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!

Vanity Fair has excerpts from various sections of the upcoming book True Prep: It's a Whole New Old World, written by Lisa Birnbach as a sequel to her 1980 bestseller The Official Preppy Handbook. TOPH (a complete scan of which can be found here) was apparently originally intended to be a humour book, but over the years many have adopted it as an earnest guide to creating the ideal preppy lifestyle. Sadly, the book is now significantly outdated, with all its meticulously-researched addresses, phone numbers, and postal rates having become all but useless to the modern reader. Combine that with the recent resurgence in preppy style and the fact that the original is long out of print, and is it any wonder that a sequel should arrive? 

True Prep is essentially conceived as an update of the original, to reflect social changes that have occurred in the last 30 years. For example:

If, in 1980, you had whispered to friends that within the next few decades America would elect a thin, black, preppy, basketball-playing lawyer to be president, they would have laughed at you and exhaled [smoke] in your face, inside the restaurant or club where you were sitting.

Now, contrary to what you might first assume, TOPH wasn't just a style guide, but an insight into an entire way of life, covering not only the "correct" schools, sports, decor and pets, but also delving into more abstract topics, such as attitudes and manners. The excerpts from True Prep show that it contains the same breadth of coverage as the original, discussing not only the pedigree and size of logos on polo shirts—unquestionably a topic of grave concern—but also matters like demographics, career choices, and the importance of frugality.

I'm hugely looking forward to this book. Not having been "to the madras born," as it were, it's hard enough to understand true prep even with the assistance of TOPH, let alone trying to figure out what it means to be preppy in 2010 rather than in the '80s. But of course, as this is a style blog, I'm most looking forward to their thoughts on changes in preppy clothing, particularly those "recent prep brands we are forced to recognize." What are the fates of J.Crew and Ralph Lauren? Inquiring minds want to know! And I, for one, am placing my pre-order ASAP.

I'll leave you with a True Prep Preppy Playlist, courtesy of publisher Knopf Doubleday.

Let me explain. For a long time, I thought very poorly of men who wore pink shirts. To me, it just screamed "LOOK AT ME! LOOK HOW SECURE IN MY MASCULINITY I AM, FOR I AM WEARING A SHIRT IN A STEREOTYPICALLY FEMININE COLOUR!" I never even thought pink was a colour that looked particularly good on men; it seemed like a man would only wear it if he had something to prove. Also, it didn't help that the only pink shirts I had ever seen were either (a) dress shirts worn by greasy Gino/Eurotrash types—the types who would also wear iridescent ties and white square-toed loafers—or (b) polo shirts with the collars popped. In other words, only douchebags wore pink shirts. What's more, once I started to become more fashion-conscious, I realized that pink dress shirts were a fad, and I knew that those men would look back in 20 years at pictures of themselves and shake their heads at how ridiculous they looked.

But all those preconceptions changed when I started learning about preppy style. I realized that pink shirts weren't a fad; they had, in fact, been worn for decades by men who were extremely traditional. Actually, I should qualify that: pink dress shirts are, indeed, a fad. But polo shirts and oxford shirts, made by the likes of Lacoste and Brooks Brothers, had been popular in pink since well before 1980, when Lisa Birnbach published The Official Preppy Handbook. As she wrote at page 141:

The classic shirt is the Brooks Brothers button-down all-cotton oxford cloth shirt. Pink is the most famous color, and it is widely supposed that no one except Brooks has ever been able to achieve that perfect pink or that perfect roll to the collar.

Christian Chensvold, of the blog Ivy Style, traced the phenomenon in greater detail in an article for The Rake magazine:

Like the white flannels of the English gentleman, colorful sportswear signals the wearer is at play, not work. Easily soiled, the clothing is thus impractical, making it a symbol of both conspicuous consumption and conspicuous leisure. “Navy blue aside,” notes Paul Fussell in “Class,” his 1983 classic on the American status system, “colors are classier the more pastel or faded.”

“You wouldn’t have someone not from money walking around in clothing that would draw a lot of attention to himself,” explains [author and custom clothier Alan] Flusser. “Up to the ’60s it was always a brahmin, upper-class thing, because they could wear it and not be laughed at.” For Flusser, the postwar starting point of the look is Brooks Brothers’ celebrated pink oxford-cloth buttondown. “Pink symbolizes this whole subject matter,” he says. “Imagine a guy wearing a pink shirt: If people didn’t understand what that was about, you had to be prepared to be laughed at.”

“When my brother was at Harvard,” Flusser continues, “the kids were wearing blazers and red or yellow pants and would always use color in some sort of interesting way. There was a sense of who could wear the most outrageous tattersall vest. But being able to wear that kind of clothing comes from a certain lineage where you felt, ‘This is what we do, and if people don’t understand it, they don’t understand it.’”

So all it took for me to change my attitude completely towards this particular garment was to change my mental association from negative to positive. Pink shirts—polos and oxfords, anyway—were no longer douchey; they were preppy. I didn't want to be douchey; I did want to be preppy (essentially because of the associations recounted above by Chensvold, as well as others on which I'll be expanding in a future post). The conclusion was simple and obvious: pink shirts are good. So when I had the opportunity recently to acquire a Ralph Lauren polo shirt in the staple "Carmel Pink" shade for less than $20, I jumped at it. I wore it today—the first time I had ever worn a pink shirt. I wore it with lime green shorts, and then out to dinner with white linen pants and navy boat shoes. And, though you might say it's bull, I felt like a Brahmin.

I like to think that I'll look back on 2010 as my "Summer of Prep," the year that I finally came home to the style that suits me best, and towards which I've always tended to gravitate. You see, throughout my teen and young adult years, my casual summer wardrobe was fairly uninspired. I always had summer jobs, so I was focused on work clothes. (Perhaps it's fortunate that I haven't bought many summer clothes until now; it's taken me this long to figure out how they should fit!) This year, though, I haven't been working for most of the summer, so I seized the opportunity to expand my wardrobe with colourful shorts, polo shirts, boat shoes, and ribbon belts—all those perfect preppy staples.

In the process, I've really started to become a fan of Brooks Brothers. Not really in terms of wearing the merchandise, since their sizing tends to be problematic for me and it's hard to get the stuff in Canada, so much as in admiring their aesthetic. I love how they manage to be both timeless and of-the-moment, while infusing their clothes with more colour and vibrancy than you typically get even from someplace like J. Crew.

Now that fall is peeking around the corner, I'll have the opportunity to think about what prep means for the cooler months. Unquestionably, it means layering, and sweaters galore, particularly cardigans and cable-knits. As far as colours, I'm thinking vibrant orange, chocolate brown, and jewel tones, along with the usual staples of blue, white, and green. I'd say I'm generally a fan of rich, rather than bright, colours for colder weather. I've got a pair of burgundy pants from Club Monaco that I'm itching to break out, which I'll probably wear with brown suede tassel loafers.

And of course, I'm digging the styles showcased in Brooks' Fall Preview 2010. I can safely say that there is nothing there that I wouldn't love to wear. They really do have something for everybody, and I don't think you could go wrong pulling out any or all of those looks to inspire yourself this fall.

In my introductory entry, I suggested that most men should be more aware of the power of their clothes as tools for expressing, and even constructing, their selves. But what if you go too far the other way? What if clothes are all that’s important to you, and you have little or no sense of self outside of the clothes that you own and wear?

To some extent, everyone reflects who they are through the clothes that they wear. It helps you express your individuality and be more in touch with yourself, and it also lets you tell people something about who you are as a person. It only becomes problematic when your sense of self is incomplete. I think this is the position in which teenagers often find themselves. For example, I'll bet just about everybody of my generation knew someone who turned into a goth in high school. Why? Because they were trying to figure out who they were and who they wanted to be, so they were trying on different identities to find one that felt right. The healthy thing to do, I suppose, is to eventually come to a conclusion about who you are, and move forward with your life. But what if you don't?

Suppose you never finished figuring out who you are (or didn't like the person you thought you were becoming), but you had a pretty good idea of who you wanted to be. Well then, you might just fill in the gap with whatever clothes best reflected the ideal person you wished you were. You'd probably also form emotional connections with particular items of clothing, or clothing brands, whose marketing images resonated with the ideal you and your ideal life. If you dreamt of country estates, yachts and trust funds, you might stock your closet with Ralph Lauren and boat shoes; if you wanted to feel sexy and desirable, the centre of attention, maybe you'd splurge at Dolce & Gabbana or quest for the perfect black leather jacket.

Brands, in particular, have a special power, because they can pack a whole array of images and associations and fantasies into one little logo, then conjure them up again instantly whenever you see that logo. That little embroidered polo player, those little embossed initials, are shorthand for every advertisement you've ever seen, every concept and image you've ever known to be associated with that brand. No wonder that fragrances and accessories, the least-expensive products sold by virtually every fashion house, also comprise the majority of their revenue. After all, not everyone can afford $2000 for a Dolce & Gabbana suit, but just about everyone who cares to can afford $60 for a bottle of D&G cologne—to buy into the fantasy.

Everybody does this, of course. Women wear heels and lingerie when they want to feel sexy; for men, maybe it's a flashy new blazer or your favourite (lucky?) clubbing shirt. I know a certain lawyer who always seems to be wearing the same Burberry tie whenever I see him in a photograph. Now, there's a slight element of costume whenever you wear something deliberately to make a particular impression, or to make yourself feel different. It's only a problem if you're wearing that costume all the time, and you get so wrapped up in maintaining your image that you forget—or don't have the headspace—to make time for anything else.

Test yourself, fashionistos: If you were forced to stop shopping and wear a uniform every day, would you still feel like yourself? Or would there suddenly be a gaping hole in your identity? If you really care about clothes, the answer is probably yes... but if you couldn't find something else to care about instead, you may have a problem.

...apart, that is, from the fact that my friends and relatives kept telling me that I should. Because you know, there are already plenty of great blogs out there. Do I really have anything new and valuable to contribute? I mean, I’m not an expert or anything. I don’t work for GQ; I don’t have a standing invitation to Fashion Week; I don’t take pretentious photographs of people posing on cobblestone streets beside vintage bicycles with cigarettes dangling languorously from their fingers and/or lips. And, in spite of the fact that I’m a lawyer, I don’t even have the money to buy all the lovely clothes that I want, because I’m still young and broke. So what have I got to say, really?

I think my answer is the same as a lot of bloggers: I have some things that I feel that I need to say, and I believe that other people might derive some value from hearing them. Despite the fact that my interest is amateur rather than professional, I make it my business to be well-informed; I hate to put forward an opinion about something if I haven’t first taken the trouble to educate myself about it, which hopefully means that people will learn something from me. And—perhaps because of my legal training, but probably because it’s just the kind of person I am—I take a very analytical approach to things, and I always like to know whether there are rules that ought to be followed, and then to help other people learn those rules. The great thing about men’s style is that, although there are rules, they’re not that hard to learn, even though there are a lot of them. And you do need to learn them—learn them well enough to follow them perfectly—before you can even think about bending them.

The other reason I started this blog is because we all have to face one simple truth: Clothes are important, and people judge you by them. I may wear a razor-sharp suit to work every day to impress my clients, while my programmer friend may wear whatever T-shirt happens to be on top of the pile of clean laundry, but every clothing choice that each of us makes tells the world something about us. The people we pass on the street each day don’t know our life stories. Through the things we choose to put on our backs, we influence how those people will perceive us.

As anyone who’s ever taken an English class knows, though, meaning is more often found in the eye of the beholder than in the intention of the creator. One man’s razor-sharp suit is another man’s totem of corporatist hegemony; one woman’s dreadlocks are another woman’s public health nuisance. Hence, the all-important question: Who are you trying to speak to with your clothes, and are they hearing what you want them to hear?

My goal is to make you more aware of the power that your clothes wield—both to express your identity, and indeed, to create it.

Or, to put it simply: Threads count.