As a follow-up to my beginner's guide, in this edition I'll share some pointers for fine-tuning your attire, and in particular, how to make your existing clothes look better. In dressing, as with most things, the details often make the difference between glorious, soaring success and dismal, soul-crushing failure.

1. Suppress Your Waist
I've said it before, and I'll say it again: the ideal male body is supposed to have a triangular torso, wider in the shoulders and chest than in the waist. To achieve this ideal shape (or the illusion thereof), a suit jacket should taper inward at the waist, rather than falling straight down from the underarm to the hip. This tapering is known as "waist suppression." Ever wonder why your suits never look as good as movie stars' do? Waist suppression may be the answer (that, and the fact that their suits probably cost 5-10 times as much as ours). Now, many suit jackets, especially the less expensive, don't come this way off the rack, but even if they do, you should engage the services of a tailor to alter the jacket in order to achieve the most flattering shape for your body. Note that, if the fabric of the jacket wrinkles in a pronounced "X" shape when the button is done up, you've got too much waist suppression, and the jacket is too tight. A good rule of thumb is that, when the jacket is buttoned, you should be able to fit your clenched fist inside of it, between your stomach and the fabric—no more, no less.

2. Hem Your Damn Pants

Shoes, Bruno Magli. Pants, After Six.
I couldn't count the number of times that I've seen men with a veritable puddle of excess pant length pooled around their ankles. It makes them look absolutely slovenly! There's really no excuse for this offence; a proper pant hem can be had for $10 or less at every quick-service mall alteration shop in the land. But the key to a perfect hem lies in you, the customer, giving proper and precise instructions. First of all, be sure that you're wearing your dress shoes, i.e. the ones that you'll be wearing most often when you wear the pants. Then, I usually request that the back of the hem fall half an inch above the top of the heel, and also to have the hem angled so that the front is slightly shorter than the back. This keeps the break neat and tidy.*

* Theoretical background: Think of the crease in the front of your dress pant as a straight line, falling from your thigh all the way to your foot. If you had no excess fabric, the pant leg would fall uninterruptedly down, barely touching your shoe, and would flap around your ankle as you walk. A little bit of extra fabric creates a "break" in the line of the crease, and allows the hem of your pant to stay more in contact with your shoe as you walk, minimizing the undesirable "flapping" effect. Too much extra fabric just looks sloppy.

3. Shorten Your Damn Sleeves
Can you tell I'm a little bit frustrated here? Even Conan O'Brien, an otherwise nearly-impeccably-attired man, is guilty of this transgression. In the simplest terms: when you are standing with your jacket on and your arms at your sides, do not allow your jacket's sleeve to entirely cover your shirt's sleeve. The jacket sleeve should be short enough that one-half inch of shirt cuff (or perhaps a smidge less) is visible past the end of the jacket sleeve. Aesthetically speaking, the contrast created by the shirt attracts attention to the hands, one of the only areas of flesh visible when a man is wearing a suit. I also think that without it, jacket sleeves just look too long—as if they're on the verge of falling over your hands. Also, if you're wearing a French-cuff shirt, no one will ever see your cufflinks.

4. Try a Pocket Square
Whether it's a stark Mad-Men-esque strip of pure white linen or a devil-may-care spray of asymmetrical silk points, a pocket square instantly ups the style factor of any outfit. Although they fell out of favour in the nineties (along with just about every other tenet of proper masculine dressing), pocket squares have been back in a big way for the last 5-10 years, and show no signs of going away—at least not as long as Don, Roger, and the gang keep pouring Old Fashioneds. Style gurus often say that your pocket square should be of a different fabric from your tie: a silk tie calls for a linen or cotton square, while a cotton or wool tie necessitates a silk square. I personally don't think it matters that much; actually, I prefer to coordinate the fabrics, to avoid a jarring contrast. However, your pocket square should never match your tie; rather, it should pick up a colour in it, or from another of the elements of your outfit above the waist. If you're feeling foppish, try matching your pocket square to your socks, but be warned that this is an advanced manoeuvre and should not be attempted by amateurs.

5. For Further Festive Frivolity, Fun Footwear Makes Fine Fare
Socks, Polo Ralph Lauren.
 Normally, I don't really like zany socks, especially the multicoloured candy-striped versions I've been seeing on otherwise well-dressed men for the last few years. To me, they seem like a useless trend, an excuse for upscale menswear retailers to charge you $25 or more for something you absolutely don't need. But you can't go wrong with a classic Argyle pattern, like the one on the left. Under no circumstances, however, should it be paired with a suit (I was wearing a blue blazer with those grey pants). On the other hand, a subtle seasonal solid colour, like burgundy or forest green, will go nicely with a either a suit or casual clothes. For an added dash of panache, coordinate the socks with one of your other accessories. This would be a bit over-the-top for business wear, but hey, it's the holidays! Cut loose and have fun.

Slippers, H&M.
If you're feeling even more dandyish, you might try a pair of embroidered velvet slippers. For those who don't own a burgundy velvet smoking jacket, they may be just the thing to add a touch of Hefnerian loucheness to your wardrobe. Perhaps the best-known are made in England by Stubbs & Wootton, but if you're like me, you'll probably find the $400 price tag rather steep for the amount of use you'd get out of them. Instead, consider this pair from H&M, a relative steal at $35 ($30 in the U.S.). Bonus points if your last name starts with a "C." They're not for the faint of heart, but if you want to make a statement (or are going stag to a New Year's party and need an icebreaker), I can't think of a better footwear choice. Just wait until you get inside to change into them, won't you? Road salt is definitely not the kind of stain that you'd expect to find on your clothes after a good party.


Men: do you not know the first thing about dressing up? Ladies: are you sick of your man looking like a schlub? Want to dress better but don't know where to start? Look no further. I've compiled the following list of tips which, taken together, will go a long way towards making you look more like Conan O'Brien and less like Conan the Barbarian. If you're pressed for time (or are just efficient), all you really need to read is the bold-face text, but the subsequent explanations will add context and clarity.

1. Never, EVER button the bottom button of a single-breasted jacket.
Why not? Well, logically speaking, it's because a properly-tailored jacket is designed to flare out slightly at the hips, to give you more room when walking or sitting, so if you try to do up the bottom button, it will be too tight. But illogically speaking, you just don't do it. Period. It's just one of those rules. I didn't make it up; I'm just telling you so that you don't look silly to people who know the rules. (N.B.: For double-breasted jackets, all buttons should always be kept buttoned unless you're sitting down.)

2. The bottom tip of your tie should fall in the middle of your belt buckle.
This isn't always easy to accomplish for shorter men or men with small necks, because we don't tend to use up enough of the tie. The problem can often be solved by using a different tie knot. For most men, the knot they know how to tie—the one they were taught by their dad, or by some chagrined girlfriend 15 minutes before leaving for a semi-formal function—is the four-in-hand. It's a compact knot that forms an asymmetrical (scalene) triangle. Now, if you find yourself with too much tie, try the half-Windsor. It's a slightly more bulky knot that forms a symmetrical (isosceles) triangle. It also uses more of the length of your tie, because you wrap the tie around an extra time before finishing the knot. Result: no more sloppy extra length.

Bonus tip: Always allow yourself a minimum of 10 minutes to tie your tie. This prevents you from feeling rushed when you're getting ready, and gives you enough time to retie several times if you don't get it right the first time (and it will be a miracle if you do).

3. Chinos are not semi-formal, unless you wear them with a jacket.
"Chino" is the generic term for a khaki-style pant (i.e. one made of cotton) that's not khaki-coloured. If you're invited to a holiday party with a semi-formal dress code, wearing chinos with a dress shirt and tie is not good enough. At a minimum, you should wear dress pants. The only exception to this is when you're wearing chinos with an odd jacket (sport coat or blazer).

Bonus tip: An "odd jacket" is any jacket that is not part of a suit, i.e. not worn with trousers made from the same fabric. A "blazer" is a solid-coloured jacket with metal buttons. A "sport coat" is a patterned jacket with plastic, horn, or leather buttons. A solid-coloured jacket with plastic buttons of the same colour as its fabric should not, in most cases, be worn as an odd jacket.

4. Pleated pants don't look good on anyone.
If you're thin, pleated pants add bulk to your thighs and midsection. If you're not thin, pleated pants put more fabric and detailing in the area towards which you least want to draw attention. Flat-front pants look better on everyone, and are always correct.

5. These are not dress shoes.
These are casual slip-ons, and ugly ones at that. A dress shoe is (for the most part) plain, unembellished, simple, and elegant, ideally with a leather sole. If you only have one pair of dress shoes, they MUST lace up. (Some dress shoes are slip-ons, but these are for the most part monkstrap loafers, which are unusual enough that they should really only be your third or fourth pair of dress shoes.)

The following is the prototypical dress shoe, the Park Avenue model by Allen Edmonds:

The piece of leather across the toe part of the shoe is called a "cap toe." Plain black cap-toe laceups such as these are perfect for any formal or semi-formal occasion. They can be bought for less than $100 by manufacturers such as Florsheim and Bostonian. Please invest in a pair. If you only wear them a few times a year, they'll last a long time, and they'll never go out of style.

Bonus tip: Buy shoe trees as well. Shoe trees are spring-loaded pieces of cedar carved in the shape of feet, which you put into dress shoes while you're not wearing them so that they maintain their shape and don't crease too much where your foot bends. A $20 investment in a decent pair of shoe trees will dramatically extend the life of your shoes.

6. Nor are these dress socks.
The same socks that you'd wear with jeans or other casual pants are absolutely not acceptable for semi- or formal wear. You need dress socks, which are very thin, because they are designed not to interfere with the close fit of dress shoes. They are usually made of cotton, wool, or a rayon blend. (I personally swear by Calvin Klein socks, which can be gotten fairly cheaply at your local Winners/TJ Maxx/Marshalls/TK Maxx.) If you've never worn dress socks before, you may imagine at first that they feel like pantyhose. This feeling will go away. Please note that you should match the colour of your socks to your pants, not your shoes.

Bonus tip: Always wash dress socks inside-out in cold water to prevent fading.

7. A dress shirt collar is supposed to fit snugly.
This is so that, when you button the top button and put on a tie, there won't be a gap between the collar and your neck. If there is a visible gap between your collar and your neck anywhere around the circumference, your collar is too big. You should be able to fit two fingers in between the shirt and your neck, and that's all. If you want to be sure of a correct fit, have a friend take a flexible sewing tape measure and measure around your neck where a shirt collar would be. Note the measurement to the nearest half-inch. Now, when you go to a store to buy a shirt, buy a shirt which is sized one-half inch larger than your actual neck measurement. To ensure accuracy, you can unfold and unbutton the shirt, and then measure the back of the shirt's neck from the middle of the button to the middle of the buttonhole. Again, this should be one-half inch larger than your actual neck measurement.

Bonus tip: Your tie should always be darker than your shirt. If you must wear a very dark or black dress shirt, minimize the contrast between the shirt and tie. Also, always take dark dress shirts to the dry-cleaner so that they don't fade, and be sure to specify that you want them dry-cleaned, not laundered. Light-coloured dress shirts should be machine-washed on warm and hung to dry, never put in the dryer (unless you want them to shrink).

That's all for now. Check back soon, when I'll present the advanced version of this guide, with tips on how to make your suit fit like a movie star's.


The Innovative Design Protection and Piracy Prohibition Act, S. 3728, is a piece of U.S. legislation created to protect innovative fashion designs from being copied (knocked off/pirated) before their creators can legitimately profit from them. It's the successor to the Design Piracy Prohibition Act, which had been before Congress in 2008/2009. The IDPPPA still needs to be voted on in both the House and Senate, as well as receive presidential signature, before it becomes law.

[Forgive me if this part gets a little technical; I am, after all, a lawyer by trade.] The bill proposes a short, 3-year term of protection for truly novel and innovative fashion designs. (Old designs will remain unprotected.) It would amend chapter 13 of the U.S. Copyright Act, which currently applies only to vessel hulls. Designers will not be required to register designs in order for them to be protected, which makes the protection more in the nature of copyright than of patent or trademark; however, the standard for a design to be found infringing is one of being "substantially identical" to the original, which standard is more or less borrowed from trademark law.

Big deal, you say. Why should I pay $300 for something when somebody else is selling something virtually identical for $30? Because, when someone copies a new fashion design, they are depriving the original designer of the ability to profit from selling the design, and those profits are necessary to ensure that the designer's business remains financially viable. It's the same basic principle as patent law: if you don't stop people from stealing inventions, nobody will want to invent because they can't make any money doing it (not to mention recouping their development costs), and society as a whole will be disadvantaged by a lack of new innovations.

I could talk about this for hours. It's such a fascinating area of law to me. Thanks to Susan Scafidi of the fashion/law blog Counterfeit Chic for keeping us updated on this legislation. Click here to read her update on the current status of the bill, and click here for her summary of the bill's provisions.


TOMMY at Yorkdale Shopping Centre, Toronto.
Tommy Hilfiger opened a handful of new stores last month under a new banner: TOMMY. But there's something very different going on here. You see, ordinarily, when I think "Tommy Hilfiger," I think of button-down shirts, khakis, and V-neck sweaters: that kind of just-slightly-dressed-up, office-appropriate, not-quite-casualwear that took over most workplaces in the late 1990s. (Some people might also think of oversized sweatshirts and baggy gangsta jeans, if they're recalling how the brand was hijacked from its preppy roots by street culture.) The corporate-casual side of Tommy Hilfiger is a rather sanitized version of prep, without much personality or unique appeal; it lacks the colourful palette of Brooks Brothers, the urban edge of J.Crew, the WASP sophistication of Ralph Lauren, the pedigreed authenticity of J. Press.

TOMMY, on the other hand, has personality. Attitude, even. It's got a few of the preppy staples—Oxford shirts, khakis, crewneck sweaters—but most of the clothes have twists to them: bright colours, bold stripes, contrast trims, inverted seams, zany patterns, and so forth. Check out the microsite to get a better feel for the clothes. It's a much more youthful approach to what Tommy Hilfiger is known for, and seems intended to compete with the likes of American Eagle, H&M, et al. It's slightly hipster-ish, unfortunately, but we traditionalists can work around that by combining things in the right way.

The interior of the TOMMY store at Yorkdale.
What I like best about the line, though, is the fit. Being a 34 chest/30 waist, it's virtually impossible to find shirts and sweaters that fit close to my body, while also having a small enough collar size and/or long enough sleeves. TOMMY, I'm pleased to report, delivers on both fronts. I'm also pleased at the price point: oxford shirts, khakis, and 100% wool sweaters all seem to be in the neighbourhood of $60, with promotional discounts further sweetening the deal. When I was there this past weekend, they were offering $20 off any one (maybe all?) sweater, plus 20% off your entire purchase—so that $60 sweater became a $35 sweater, after tax. I took the opportunity to add a classic grey crewneck with turn-back cuffs to my wardrobe.

TOMMY has two standalone stores in Canada (both in the Toronto area) as well as two in New York state, but the line is or will soon be available at all mainline Tommy Hilfiger stores in Canada. And don't forget to sneak a peek at the Spring 2011 collection over at GQ.


In the footsteps of their past designer collaborations, H&M will be releasing its latest, with Lanvin, on November 20th in select stores. British GQ.com has exclusive photos and an interview discussing the collection right here.


Brand new today from Brooks Brothers, the Home Collection is available exclusively online and features bedding, towels, bathrobes, slippers, and decorative pillows. I'm absolutely in love with the repp-striped cushions! Well... with everything, actually.


I had the pleasure of meeting Lisa Birnbach, author of True Prep, in Toronto this past Tuesday, October 12th. It was an intimate little event at the Cole Haan store on Bloor Street West. Among other things, I was able to chat with Lisa about preppy fragrances (she posited Aramis as a possible successor to Eau Sauvage) and her appearance on The Colbert Report (he cautioned her to remember that "Stephen Colbert" attended Dartmouth, not Hampden-Sydney). I was thrilled when she complimented me on my watch (vintage, by Vantage, a Hamilton second line), and when the conversation turned to the disadvantages of Canadian autumn weather—which sadly all but necessitates the wearing of socks—I even earned a hug for proudly revealing my bare ankles in defiance of the 13°C (55°F) temperature. And as if that didn't make the event memorable enough, notice that the "To Do" list on the book's back jacket is dated October 12! (And yes, that's her handwriting in the picture at left.) I had a truly fantastic time.

And I can also report on the actual substance of the book, since I've finally finished reading it. First of all, if you were a fan of the original 1980 Official Preppy Handbook, True Prep certainly will not disappoint. It contains updated information on essential topics like schools, clubs, vacation destinations, and domestic employees, as well as new coverage of touchy subjects such as adoption, divorce, diversity, death, and scandal. However, if you're new to the whole "preppy" thing, in some ways I don't think True Prep makes quite as good an entrée as did the original OPH. I've heard at least one other person say that there's less explaining being done this time around, and I'm inclined to agree.

Unfortunately, nowhere is this more true than in the section on fashion and style. The original Handbook was invaluable for the excruciating detail with which it catalogued the necessary elements of the prep wardrobe, right down to the fiber content of shirts and the widths of ties and pant cuffs. The sequel, by contrast, paints the wardrobe section in rather broad strokes, with one notable (and welcome) exception being the section on polo shirt logos. I also found it helpful that the authors took the time to give their seal of approval to several brands not featured in the original, both expected (J.Crew, Vineyard Vines) and not (Hermès, Verdura). As for Ralph Lauren: they gave him an entire page to himself (pictured at right), and even apologized for not including the brand in the original!

One thing I found odd about the book is that, much as I've been given to understand that the original OPH was intended to be satirical and tongue-in-cheek, the promotional angle that's being taken for True Prep makes it seem as though it takes itself much more seriously. Sure, there are knowing winks here and there, but I really don't get any sense that the authors view their subject-matter with particular irreverence, or as anything approaching a joke. This makes the book more valuable as a social chronicle, but perhaps less valuable as a work of satire.

Now let's talk about the book's title. True Prep. The closest thing to an explanation within the book's pages is the introductory Manifesto (pictured at left). But this is really not what I imagined when I first heard the phrase "True Prep." To me, true prep would have to be more specific, more pedigreed, and more circumscribed than anything that this book espouses. As I mentioned in a previous entry, one has to question how "true" the prep is if anyone can be preppy. Like Mark Oppenheimer in Slate, I wondered what the difference was between truly being prep, and merely performing prep. To me, true prep would almost have to be inherited, "bred-in" if you will, and would definitely require immersion from birth. I feel like you almost certainly wouldn't qualify if you had ever tried to be preppy, if you were ever conscious of the question of whether or not something was preppy (of which I'm undoubtedly guilty).

The closest analog would be, I suppose, an accent. You can't just start speaking with an English accent halfway through your life. It's only authentic if you develop it naturally when you're young. You either have it or you don't. To cultivate it later in life—how can that be anything other than phony?

I don't know the answer to that question, but then, it's probably impossible to reconcile my conception of "true" prep with the authors'. They seem to posit two categories of prep identifiers: tangible (clothes, houses, vacations, schooling, leisure activities) and intangible (attitude, demeanour, discretion, manners). Neither is sufficient, and both are necessary. And it seems that the intangibles are probably the most important; you can't be preppy if you're a boor, no matter how picturesque your beach house or how salt-stained your Top-Siders. I think that to really live up to its name, the book should have spent more time on the intangibles. It does have an etiquette chapter, but that's only one out of twelve, and it's hardly the beefiest of them all.  But fortunately, you can do something to make up the difference: contact the bookstore of Hampden-Sydney College and order yourself a copy of To Manner Born, To Manners Bred: A Hip-Pocket Guide to Etiquette for the Hampden-Sydney Man. It costs only $4.95 plus shipping.

In the end, though, that's all just a lot of nitpicking. True Prep is a cracking fun read, and a truly enjoyable book. I'm very glad to have my own (autographed!!!) copy.


A collaboration between Street Etiquette and Unabashedly Prep has been making waves in the style blogosphere over the past week. The project, entitled "The Black Ivy," is a set of photos depicting several  preppy black students going about their daily lives around the campus of the City College of New York. The slideshow concludes with a different series of photos, shot by Alfred Eisenstaedt at Howard University (one of America's historic black colleges) in 1946. Rather than any racial implications of either photoset, their juxtaposition got me thinking about the interrelationship between style and fashion, and particularly how fashion trends tend to date clothes.

Let's take a look first at these two photos from 1946. You'll notice many ways in which the suits of that era differ from the suits of today: higher-waisted trousers with wider legs, plus longer jackets that had wider lapels, longer sleeves, and higher button placements. And of course, hats were fairly common for everyday wear in 1946, whereas now they're exclusively reserved for the realm of fashion statement.

What we're seeing here is representative of the very particular way that men's fashion tends to change over time. That is to say: Men's fashion is a series of deviations away from one universal reference point. This reference point (or, for the Aristotelians in the room, the "Golden Mean") is a particular point in time, usually around the origination of the garment in question, which sets the standard for all subsequent iterations of that garment. In the case of suits, the reference point is the classic British/Savile Row cut of the 1930s (see photo at right). And the reason why I call it the "Golden Mean" is that the reference point is usually perfectly in balance with the proportions of its wearer, because (in the realm of suiting at least) the garment would have originally been custom-made to fit its particular wearer's body. No aspect of the garment is exaggerated or out of proportion; everything is perfectly suited to the particular individual. The width of the trouser leg is in proportion to the wearer's shoe size; the width of the lapel is in proportion to the breadth of the wearer's shoulders; the placement of the jacket's buttons and the height of the waist of the trousers are in proportion to the wearer's overall height. And, when you have a suit that conforms to the Golden Mean, it becomes nearly impossible to date. It is timeless. That's the reason why the evil EPA agent in Ghostbusters would still look perfectly well-dressed if he brought his suit from 1984 to today: because it is, essentially, outside of fashion.

Bearing that in mind, let's now consider one of the modern-day Black Ivy photos.

What we see here is a deviation in the opposite direction from the 1946 photos. In 1946, it was all about more and bigger: longer jackets, wider lapels, wider pant legs, longer hems. In 2010 (and for pretty much the last decade), it's all about less and smaller: shorter jackets, narrower lapels, skinnier pant legs, shorter hems. Note the fellow in the middle, wearing the light grey sport jacket with jeans: the width of his pant leg is ludicrously narrow relative to his shoe size. The chap with the tan striped sport coat? It's so short that it's barely covering his ass. Also note the two guys with their skinny pant legs cuffed or rolled a few inches above their shoes. Sure, this looks spiffy now, because it's 100% on-trend in the minds of those who follow fashion. But ten or twenty or sixty years down the road, these sticklike pants will look just as ridiculous in retrospect as those tentlike '40s pants do to us now.

Contrast those outfits with the one at left. Admittedly, the shawl-collar cardigan with toggle closure is a bit of a trendy style. But it references classics from the past history of menswear; shawl collars and toggle closures are both authentic details, though not necessarily on the same garment. And more importantly, the fit of what he's wearing is relatively timeless. The khakis are neither tight nor loose, long nor short, skinny nor wide; they're perfectly proportionate in every way. Likewise, the fit of the sweater is close, but not tight. In short, everything balances. No one aspect of the ensemble stands out as being exaggerated in any direction.
The lesson here: When you're putting together an outfit, avoid trendy extremes to avoid dating yourself. Don't go for the jacket with the 1.5-inch lapels or the pants with the 7-inch leg opening. Think first and foremost about what suits you: your body, your personality. Wearing things just because they're fashionable (hello, square-toed loafers and multicolor-striped shirts) is the surest way to look back ten years from now and regret every photo ever taken of you. Instead, dress to suit yourself. That way, you'll avoid becoming a fashion victim, and instead grow further towards your own personal style.


I posted the following as my Facebook status earlier today:

Attention, Wal-Mart shoppers: Would it kill you to put on a pair of freaking khakis? You look like shit. Seriously.
My brother-in-law's girlfriend left the first comment. I decided to use it as the title of this post. It got me thinking about why I said what I said, what I was really trying to say, and how the message may have gotten skewed by the way I chose to say it.

First off, I'm not asking for people to “dress up” when they go to Wal-Mart. I recognize there's an appropriate time and place for dressing up. I don't expect the average Wal-Mart shopper to look as nice as the average Michelin-starred restaurant-goer. (As one of my other friends archly observed, “Extensive socioeconomic research has actually revealed that many lower income families are unable to afford tuxedos for everyday wear.”) But the issue isn't “dressing up.” It's really just “dressing nicely.” Just a modicum of effort to not look terrible.

Image from http://www.peopleofwalmart.com
I like to think of it as analogous to proper spelling and grammar use on the Internet. The fact that it does require some effort to present yourself well, coupled with the comforting shield of anonymity (“I'm not going to see anybody I know”), may tempt you to let your standards slip, just because it's easier. It's not like it's a job interview, right? It's not your resume! It's just the Internet! It's just Wal-Mart, for God's sake! It's not like people are judging you based on what you're wearing!

And that, in fact, is the crucial assumption: people are judging you, no matter where you go. You might think that they're too busy trying to get everything they need so they can get home and cook dinner, and maybe some of them are... but probably, some of them aren't. But hey—that's okay! You don't give a damn what they think, do you? What right do they have to judge you? They don't even know you. Maybe you're dressed this way because you've got the flu, or your grandmother just died, and it was all you could do to drag your carcass out of bed to Wal-Mart to get more chicken soup and tissues.

Okay, that's fine. I suppose I can't say with certainty whether such an excuse applies to any one particular shopper, so I can't soundly make a judgment about any particular person I see based on what they're wearing on any particular day. But I think I can safely presume that it doesn't apply to everyone at Wal-Mart all the time, which means that I can soundly make a judgment about people and their appearances on a more general level.

I really think it's a shame that the common discourse (both appearance-wise and language-wise) has degenerated as far as it has. When you dress up for a job interview, and when you take the trouble to compose a typo-free resume, the effort you expend is a sign of respect for your audience. Your effort demonstrates that you do care about what they think, because you value their opinion enough to put in the effort to make sure that it's a positive one. If you don't care what people think, you don't put in the effort. So, when people put in little or no effort to make themselves presentable, I essentially see it as a sign of general disdain for the opinions of everyone who's going to see them that day. And this is why I think it's much worse to look shabby at Wal-Mart than to look shabby at the corner store: so many more people are going to see you! I just think it's unfortunate that so many people are giving this big sartorial "fuck you" to the rest of the world on such a regular basis.

All I ask is a little effort. I don't think that's unreasonable. And besides—you never know who you're going to run into.


I'm not going to go out of my way to link to every piece of True Prep media coverage, but because I love Colbert so much—and because he's part of True Prep's Preppy Pantheon—I had to post this video from last night's episode (for Canadian residents only; if you're watching in the U.S., click here.) I just wish the interview had been longer!


Less than two weeks left! I'm not going to add too much of my own commentary, but it was really interesting to hear Ellen Mirojnick's thoughts about her costume designs for Wall Street and its upcoming sequel. The fascinating thing is thinking about who the characters are, what place and time they're in, and then thinking about how you reflect that in their clothes—how does that translate into wardrobe design. The contrast that I noted earlier, for example, between Gekko's casual clothes and his suits, is actually an evolution of his character over the course of the film. The casual clothes are at the beginning, when we first meet him and when he first meets Jacob Moore. He's lost his way a little bit. And so when he gets out of the off-the-rack stuff (Canali, e.g.) and back into the custom-made suits, it's a stylistic homecoming, but also a renaissance: he has to evolve. As Mirojnick says,

I didn't want to put him in contrast collar, I didn't want to put him back to exactly what he was. He was a groundbreaker at that time — he was outshining everyone around him — so why would he go back to that? Naturally, as a person of strong personality, such forceful instinct would progress. Sharks need to move forward. If they're not moving forward they're dying.


... is because, before I went to Chapters today, I went to H&M first, and ended up buying a couple of fantastic cotton sweaters for the fall.

My wardrobe has just been crying out for cable knits, and lo, the Good Lord provideth! I am absolutely loving H&M this season because they have great preppy sweaters and shirts that actually FIT my twiglike frame. (Sweaters are a nightmare for me to find a proper fit - even Ralph Lauren's "small" and Lacoste's size 3 are way too big for me.) And after seeing a perfect navy cardigan with white tipping (not in my size), and a perfect off-white tennis sweater with navy-and-green tipping around the V-neck and cuffs (also not in my size), I decided I had to seize these two before it was too late. That's the only thing I don't like about H&M: they always run out of small sizes first.


As if Brooks Brothers hadn't already answered the question "What does prep mean for fall?"...

And unfortunately, once again, I'm flagrantly behind the times; these pics were making the rounds of the blogs in mid-to-late July. However, when I picked up my copy of the September issue of Vanity Fair (because of the True Prep preview inside), right after the Table of Contents I found Tommy Hilfiger's ad campaign for Fall 2010, entitled "Meet the Hilfigers." Photographed by Craig McDean, the campaign apparently envisions some kind of nouveau-preppy family (or loose passel of relatives, at any rate) and depicts them during a tailgate party. Visiting the Tommy Hilfiger microsite, where the members of the fictional family are profiled, all the prepquisites are there: Columbia, Wellesley, basset hounds, fundraising, Vermont vacations, socklessness. But clothing-wise, I found the photos provided ample inspiration for fall. I particularly liked the patterned sportcoats; the crested, cable-knit, and tipped sweaters; and of course, loafers galore.

I have to say that Tommy Hilfiger hasn't generally been among my favourite brands. The brand and the logo just don't have the same value to me, the same positive associations, as Ralph Lauren or Lacoste do. The clothes themselves are pretty decent, though; actually, one of my favourite pairs of khakis is Tommy, and their Custom Fit sport shirts in size extra-small are among the very very few off-the-rack items that fit my skeletally thin (or, as I'd prefer to think of it, "aristocratically slender") frame. Their sweaters, jackets and ties have never fit me, but these ads leave me hoping that I can manage to find something that does.

Click each pic to enlarge, and scroll down for a video.


Author Lisa Birnbach with Chip Kidd
With the release of True Prep only four days away, here's a quick update for those who haven't been following the latest buzz on the book's Facebook page:

And finally, an item that's three months old, but obviously not very well-publicized, since I just stumbled across it the other day: publisher Knopf has posted an 11-page sample from the book on Slideshare. (Download the PDF version here.)

I found the piece in Slate to be the most interesting and insightful of the bunch. Like many, when I first heard about the book, I wondered about the significance of the title "True Prep." (What exactly is "true prep"? Presumably the book is going to tell us. But how do the authors know, anyway?) So I was intrigued when reviewer Mark Oppenheimer said:
It's clear that, at least as far as Birnbach and Kidd see it, the leavening earnestness is gone: It's all irony now. There are no true preps, to be both admired and needled—instead, we're all just performing prep.
This Obama-era preppiness (he is preppy, too, according to our authors, as is Michelle) is a problem, because the appeal of preppiness, indeed its very inclusivity, depends on an outward exclusivity. The club should require a little effort to join. If everyone who has ever gone to a private school is preppy, then ultimately prepdom is just about money, which actually places preppiness out of reach for most people.
The authors are far too careful to [not] make preppiness identical with money; they don't present McMansions as preppy, or cruise-ship vacations. But in trying to make prepdom accessible, Kidd and Birnbach have made it less desirable. It's noteworthy that the great prep designers, from J. Press to Louis Pearlstein to Ralph Lauren to André 3000, have been non-WASPs trying to master the code of the WASP; in mastering it, minorities continue to define it. (It is entirely unsurprising that this book is by a Jewish woman and a gay man.) But if they define prep too broadly, they diminish their own success.

This time around, I do not think that Birnbach and Kidd are being prescriptive so much as descriptive. That is, they may not be leading prep fashion so much as responding to it. After all, is there a cohesive prepdom any more?
True Prep is an enjoyable but maddening wake-up call that we are watching a culture unravel, one lambswool thread at a time. If we don't snap to attention, throw on our duckboots, thread the duck's-head insignia belt, leash up the English setter, have a Pimm's Cup, and figure out what this culture is, it will be gone.
I would have said that the concept of "true prep" did require some sense of exclusivity; that's what makes it desirable to be preppy. But to hear Oppenheimer tell it, the book seems to democratize prep to nearly the point of meaninglessness. Birnbach herself said, in a different interview with Amazon from the one linked above: "Everyone can be a preppy. There’s no barrier to it. You want it? We’ll let you in."

From what I can tell, there seem to be two elements to Birnbach's "true prep": the clothes, and the lifestyle (which includes important things like discretion and manners). I gather that the point is that both of these can be acquired at any time if one doesn't already possess them. And apparently you needn't have actually attended a prep school or "one of your corduroy-jacket elbow-patch colleges" (to borrow from Stephen Colbert) to be "truly" preppy. You can see this in an interview that Birnbach did for Ivy Style back in April:
IS: One of the things that’s changed since 1980 is the commodification and parody of preppy — as in the Smirnoff “Tea Partay” commercial. In the OPH you’re describing a certain Northeastern upper middle class tribe or caste that was largely hidden from the general public. But in the last 30 years preppy has become so mainstream as a fashion style. Is there such a thing as authentic preppy anymore? And what is the significance of the new book’s title “True Prep”?

LB: The first book was a big giant reveal of a private tribe. There was a little bit of discomfort with the code being shared. I totally get that, but so be it. There wasn’t a lock and key on it. In every city I visited, I heard, “Oh, I had the idea to do this book.” It was a tempting Baedecker to create. And even when I was first working with Workman Publishing, they wanted to call it the “Preppy Catalogue,” and to be just about stuff and clothes. But there was no good way of explaining stuff and clothes without explaining context and worldview.

Is there a difference between someone wearing a polo shirt, khakis and a belt, and a preppy who went to St. Paul’s who’s wearing the same clothes? Sure there is, but it doesn’t fit the 21st century to keep people out. I can understand why someone from a certain restricted population might not want to share, but that’s really passé.

Personally, I feel the tension. On the one hand, "preppy" is valuable to me because it connotes a certain exclusive, upper-class, privileged way of life that's highly desirable. But on the other hand, I have to recognize that I myself would not qualify if the strictures of "true prep" required education at certain institutions, or a certain family pedigree. And if you want to be preppy because you like these upper-class/exclusive connotations, it diminishes the value of being preppy if anybody can do it. It's a genuine case of "I wouldn't want to belong to any club that would have me as a member."

I'll reserve judgment till I've read the whole book. But for now, colour me concerned, and a bit confused.

UPDATE: Read my review of True Prep.


With only 4 weeks left until the release of the five-months-delayed movie starring Michael Douglas and Shia LaBeouf (pronounced "shy-uh la-buff," by the way), it's time for a peek at what the film's stars will be wearing once it hits screens on September 24th.

But first, I'd like to suggest that you take a look at this excellent post at Clothes On Film for a refresher on the style of the original Wall Street. Remember the eighties: contrast collars, big suspenders, big pleats. And more importantly, remember the difference between Gordon Gekko and Bud Fox. As the linked post points out, Fox starts the movie as a very plain, conservative, Brooks-Brothers-type dresser. As he enters more fully into Gekko's world, he begins to emulate Gekko's flashier manner of dress, particularly with regard to accessories.

So too in the sequel we can see the contrast between Gekko and his new protégé, Jacob Moore. But here, the positions are reversed: Gekko is conservative and dresses like "old money," while Moore is contemporary and dresses like "new money." Just take a closer look at the movie poster up there. Gekko: three-piece suit, bengal stripe shirt, simple dotted tie, pocketwatch. Moore: single-breasted peak-lapel (SBPL) suit, white shirt, Hermès tie.

This nearly seems to be Moore's uniform, at least while he's wearing a suit. Always a SBPL suit, always a white shirt, almost always an Hermès tie. He also favours narrow trouser legs hemmed short with substantial cuffs, and appears to wear nothing but Gucci horsebit loafers with every outfit, including casualwear. And don't forget that white linen pocket square, with its artfully scalloped peaks. Much of Moore's clothing is extremely trendy, particularly the SBPL suits with the narrow legs and the cuffs. His wardrobe selections seem to have been made to reflect the Wall Street trader stereotype, the guy who buys new clothes constantly, ensuring that his wardrobe is both of-the-moment and certain to become dated. I don't want to speculate too much on what Moore's clothes mean for his character's identity without having seen the film. But I think it's worth asking whether he's dressing this way because he feels these clothes really belong to him, or whether he's trying to fit into a world where he doesn't quite feel he belongs. The $38,800 watch he apparently wears has to make you wonder a little bit about insecurity.

Gekko, by contrast, wears many more conservative pieces this time out. You might call it the "rich old white guy" look. In the HD trailer, for example, the sharp-eyed observer will spot a Canali label inside one of Gekko's jackets, a very traditionally-styled (and high-quality) line. And when Gekko walks side-by-side with Moore, the contrast becomes even more apparent: Gekko's jackets have a more conventional, slightly longer, length, with lapels of moderate width (generally notch, not peak), paired with shirts and ties of relatively muted colours and patterns. The pants are plain-hemmed, not cuffed, and fall to a normal length, while the shoes are understated lace-ups.

Gekko's wardrobe still has elements of pizzaz, of course, but they're subtler, and they seem to come out more strongly in his suits than his casual clothes. Photographed for Vanity Fair, he wears a three-piece suit with an unusual double-breasted vest, with even more unusually slanted rows of buttons. In the other photo for Vanity Fair and at right, he wears a chalk-stripe suit (with purple stripes!), purple large-foulard tie, and purple pocket square. The shirt, with its simple striping, anchors everything down and prevents it from becoming totally ludicrous (although I have to wonder whether outfits like this might be regarded in decades to come with just as much bemusement and curiosity as Gekko's eighties trainwrecks originals are today). We even see flashes of flair in suitings: right at the end of the trailer, Gekko is wearing a black suit with a strong but unidentifiable textured fabric. Essentially, Gekko tends to be conservative in the fit and cut of his suits, but brings in more contemporary (and ostentatious) elements in the choices of fabrics and accessories.

Maybe it's just because Gekko's personality is already a known quantity from the first Wall Street, but I think there can't be a doubt in anyone's mind that he absolutely owns his clothes. He takes what's already inside him and projects it outward, making his clothes match his inner self, expressing himself through his clothes. And, though he's saying it in different ways, he's saying the same thing in both movies: "I am in your face and I am bigger than you and I will destroy you if you cross me." But there's also the element of comfort there, the sense of being at home in his clothes.

The question I have about Moore is whether he's doing just the opposite of Gekko: putting clothes on on the outside, and then hoping that they can change what's on the inside. I don't get a sense of personalization from Moore's clothes; it seems like he could be thinking "this is what a trader wears and I need to look like a trader so I need to wear these clothes." It doesn't seem like it could be his personal uniform, so much as it's the uniform of an occupation that he happens to hold at the time. They're someone else's clothes, essentially. I'm interested to see whether this bears out in the plot of the movie itself.

I'd like to close by saying how amused I am that, where the filmmakers decided to ditch Gekko's classic slicked-back hairstyle, they appear to have replaced it with that of another infamous figure in the financial world: Bernie Madoff.

Left, Bernie Madoff; right, Michael Douglas as Gordon Gekko.
(Or, at least, what Madoff would have looked like if he had as much hair left as Michael Douglas does.)


Although it's three years old, I just stumbled on this excellent photoessay from TIME Magazine on JFK's personal style. It's a slideshow of pictures narrated with commentary on what made Kennedy's style so unique and influential. And it occurred to me as I was looking at these pictures that JFK's style can be seen as a combination of two huge trends in men's fashion over the last 3-4 years: traditional Americana/prep, and the '60s revival brought about in large part by the TV series Mad Men.

Left, President John F. Kennedy; right, Mad Men's Don Draper.
Look at above picture—the entire JFK slideshow, in fact—and you'll see the building blocks of Don Draper's wardrobe: narrow lapels, narrow ties, white shirts with small-proportioned point collars. But also in those pictures, especially the more casual ones, you'll see the foundational elements of classic American sportswear: button-down shirts, polos, crew-neck sweaters, khakis, sneakers, Ray-Bans.

Left, JFK; right, a page from the J.Crew September 2010 men's catalogue.
These elements are as close to timeless as you can get. They're the basic staples of the American man's wardrobe. They may pass in and out of fashion, but they are never out of style. GQ even went so far as to compile a list of "10 Things That Will Never Go Out of Style," and, while I think that it's a little too early to make a judgment call on Timberlands, I don't seriously disagree with the rest of the items they list. (Ray-Ban Wayfarers have made a rather tragic hipster comeback lately, but hopefully they'll soon return to their roots.)
Now you may argue that it's facile to compare Kennedy to a J.Crew catalogue when J.Crew doubtlessly draws conscious and perpetual inspiration from Kennedy, but in a way that's exactly the point: you can't draw perpetually from Kennedy unless there's something timeless about his clothes. And these staple clothes are the ones you'll always be able to find in stores. You could do worse than to build a wardrobe around them.

As for Mr. Draper, it could be said that the '60s skinny-suit trend is really just an iteration of the skinny-suit trend that started with Hedi Slimane and Dior Homme in the early 2000s. Really, how long were D&G (and H&M, for that matter) doing narrow lapels before Mad Men came on the air? But the Mad Men look is a little bit different: the jackets are slightly less fitted, the closures somewhat higher. The Dior Homme look was more about leanness and length and androgyny; the Mad Men look is vintage '60s, when men were men, and even a refrigerator-shaped gentleman could get away with a slender tie and lapels. I'd caution anyone against embracing it too fervently, since the pendulum is bound to swing back the other way, but I personally have one grey pinstripe slim suit from H&M in my wardrobe, and it's great fun to Draper it up with a white French-cuff shirt and a skinny black tie every now and again. All you need to top it off is a pack of Luckies, two fingers of rye, and of course, the right gel. Smashing!

...or at least, smashed.


You can always count on a pocket square to add flair and panache to an outfit. (I hope I don't have to tell you how to fold one. If so... I'll look the other way while you click here.) I get a little self-conscious wearing a pocket square to the office, though; I worry that anything other than the plain single-fold might come across as too flashy, even uppity. But one day, I had a wonderful stroke of luck while trying to achieve that perfect devil-may-care spray of asymmetrical points:

Pocket square, Hugo Boss. Jacket, H&M. Shirt, Tristan. Tie, vintage.

Such a unique shape! But what on earth was it? At the time, I thought it looked like the Guggenheim Museum in Bilbao, Spain:

But only today did I realize that this impression wasn't accurate. What it actually reminded me of was a piece of furniture: the "Tatlin" sofa, designed in 1989 by Mario Cananzi and Roberto Semprini, and manufactured by Italian furniture company Edra:

Cananzi & Semprini's design was based on a tower designed (but never constructed) by the Russian architect Vladimir Tatlin. The sofa might already be familiar to you if you're a Star Trek fan; it featured prominently in the Next Generation episode "The Most Toys," where it belonged to the unscrupulous trader and collector Kivas Fajo.

As for the pocket square? It was raining that day, and by the time I got to the office and took off my trenchcoat, the fold was ruined. I could've probably tried for half an hour and still not succeeded in duplicating it. Maybe someday I'll figure out how to do it again...


I've been writing a lot of personal thoughts and musings here in my first few entries, but I also promised to provide some concrete style rules for you guys. The most stringent rules for propriety in dress come, not surprisingly, in the world of suiting. They require significant study, care, and attention to detail before they can be mastered, which is why I've devoted a lot of time to learning about suits and their related accoutrements. So now it's time for a bit of practical advice. In no particular order:

1. Size does matter.
You need to know your size. This really should go without saying, but I can't count the number of times I've asked a guy what his jacket size is and had him tell me one way or another that he had no idea. Here's what you do: get a tape measure. Even a metal one that you'd use for measuring wood will work. Wrap the tape measure around your chest at its fullest point, usually right around the nipples. The measurement in inches is your jacket size. And chances are, if you subtract 6 inches from that, you'll get your waist size. This is how a standard suit is sized; the difference between the chest measurement and the waist measurement is called the "drop." 6 inches is the standard drop for men's suits.

Once you know your chest measurement, knowing what length of jacket (regular, tall/long, or short) to purchase is fairly straightforward. The two rules of thumb are (1) the jacket, like a good lawyer, should cover your ass, and (2) the hem of the jacket should fall roughly even with the knuckle of your thumb when your arm is at your side, though many jackets today may be an inch or even two inches shorter. Generally, if you're between 5'8" and 6', you'll probably take a Regular; outside that range, you should try both Regular and the other to see what looks best.

2. The most important fit is not the chest, but the shoulders.
Having said all of the above, the first thing you need to look at when trying on a suit is the fit of the shoulders, because in spite of what the salesman may tell you, shoulders cannot be tailored. The entire jacket is constructed around the shoulders; they are the garment's foundation, and if they don't fit, forget it. How do you tell whether they fit? The outermost point of the shoulder should not extend beyond the muscle of your upper arm. You can test it this way: if you stand perpendicular to a wall and edge sideways towards it, the shoulder of the jacket should not touch the wall before the rest of your arm does. If the jacket fails this test, go down a size. Generally speaking, if the jacket makes your shoulders look broader than they actually are, it's not a proper fit.

3. Tapered waists aren't just for women.
I will never forgive the salesman at Moores who, when I suggested that the waist of my first suit jacket needed to be taken in so that it curved closer to my body, told the 18-year-old me that "only women's suits do that." WRONG. A man's jacket should not hang straight and shapeless from his underarm to his thigh. Although suits have been cut this way from time to time over the last century, notably the "sack" suit popularized by Brooks Brothers, this shape doesn't flatter the body at all. Speaking in terms of ideals, men are supposed to have shoulders that are broader than their waist; essentially, a triangular-shaped torso is the most desirable. To create this shape (or the illusion of it), the jacket must taper in at the middle, contouring to the wearer's body so that the waist appears smaller than the shoulders and chest. This is known as "waist suppression." And regardless of the man's actual shape, tailoring a jacket this way makes him look better.

4. You need a good tailor.
It's highly unlikely that a suit will fit you perfectly right off the rack; at bare minimum, you'll have to have the pants hemmed. But it'll probably need a lot more work than that if you want it to fit like the ones you see in movies. The good news is, though, that if the jacket is a bit baggy, its sleeves are a bit too long, or the pants are a bit too big, a tailor can fix them. (Personally, my spine is little too straight at the top, so I always get a roll in the back of my jackets just below the collar that has to be corrected.) Having said that, tailoring can get expensive, and remember: he's a tailor, not a miracle worker. If the suit jacket is totally the wrong size, a tailor can't fix it. (Pants, yes, if you're prepared to pay for them to be taken apart entirely and basically re-cut into a new pair, but even then you can probably only go down one size.) The general rule is that it's usually possible to take something in, but it's not necessarily possible to let something out, because the extra fabric may simply not be there.

5. Money isn't everything.
I've heard it said many times: a $400 suit that fits properly looks better than a $2400 suit that doesn't. If you have the knowledge to properly instruct your tailor, you can make a cheap suit look pretty damn good. Sure, a $2400 suit is very nice, but if you have to wear one to the office every day, it becomes rather cost-prohibitive. Personally, as far as the lower end goes, I really like Club Monaco and Zara. They both have great designs at a sub-$400 price point which, importantly, usually come in 100% natural fibres (wool, cotton and linen). If there's one minimum standard I would advocate for a suit, it's the 100%-natural-fibre rule. You often find polyester in cheap suits at places like H&M, Le Chateau, etc., but wool is superior in every way, primarily because it looks better and wears better.

And there you have it. Coming soon: specific ideas to get more mileage out of your existing suits, using tailoring and accessories. Questions? Leave a comment!