I've been sick the last couple days, but I managed to catch The Kennedys on the History Channel last night. I am in love with this cardigan worn by Tom Wilkinson as Joe Kennedy Sr. Even the pockets have tipping!

This past Friday my wife and I visited the Salvation Army Thrift Store in the Kerr Village area of Oakville, a suburb of Toronto known for being full of rich people. I think I can fairly safely say that, at the least, people in Oakville must own really nice stuff, because what they get rid of is pretty amazing:

Each item in the above photo was $1.99, except for the shoes, which were $8.99. I don't often have good luck with clothes at thrift stores, but I can usually find at least one tie that's decent. But finding two that are so perfectly preppy is unprecedented. First we have the very nautical Chubb Marine Underwriters tie, which would look perfect with a blazer:

Silk face, polyester lining, 3 1/8" wide, made in USA.

And then of course we have the game-bird critter tie:

All silk, 3 1/2" wide, made in England.

I'm not completely certain what kind of bird it is, but going by this picture, I'm pretty sure it's a grouse.

But I think I'm probably most excited about the Sebago burgundy tassel loafers:

Leather upper, leather sole, made in USA.

I love tassel loafers, and these will go just perfectly with khakis, navy or grey dress pants - hell, even my white linen/cotton pants. Of course they need a little spit and polish, but there's nothing seriously wrong with them, so they'll clean up very nicely. They look a lot better even after just putting in shoe trees.

And the runner-up for Most Exiciting Item is definitely The Kennedys: Portrait of a Family by Richard Avedon. I actually gasped out loud when I pulled it off the shelf. It features never-before-seen family portraits of the Kennedys taken by Richard Avedon and donated to the Smithsonian before his (Avedon's) death.

Next weekend? The Oakville Value Village!

I’ve often been known to overdress. I went to a party a couple of weeks ago, and one of the hosts made fun of me for wearing a cardigan and a button-down shirt to such a casual event. He was wearing a pair of old jeans and a Carhartt T-shirt. Evidently, here was a guy who didn’t give much thought to the meaning of his clothes—even though, to the interested listener, they had plenty to say. That’s the thing about clothes: they speak for you, even if you're not paying attention. (To my mind, the way of dressing that carries the least expressive information about a person is the one that is most predicated on quantitative rather than qualitative concerns: buying the cheapest, most practical, most durable clothing one can find at mass-market or discount retailers, and wearing everything until it falls apart, regardless of changes in fashion.) But his comment got me thinking about why I wore what I wore to that party, and just generally about why I dress the way that I do. And I realized that it was, in part, a response to the way that other people dress.

As I’ve mentioned before, I believe that when people put effort into their appearance, it demonstrates respect for the people around them. But some people put effort into cultivating an appearance that is calculated to shock or affront others. Then they’re sending a different message altogether. The message that I personally get is, “Not only do I not care what you think of me, but I’ve taken the trouble to make sure you can tell that I don’t. In fact, I reject you, your values, and everything you stand for.” In other words, if no effort is a shrug, this kind of effort is a middle finger. I’m actually insulted by it.

Now, much as I’m socially liberal and unconventional in some ways, in other ways, I’m quite conservative. One of those ways is in matters of etiquette and protocol. I don’t value tradition for tradition’s sake, but in a lot of cases, I’ve made as reasoned and objective an evaluation as I can, and I’ve come to the conclusion that the traditional way is the preferable way—primarily because, at least as far as social conduct is concerned, the traditional way is the one that shows the most respect for other people and is most likely to preserve civility and courtesy in the public sphere.

So this is a significant part of why I dress the way I do: as a reaction against counterculture. Just look at me: I’m an upper-middle-class heterosexual white male, university-educated, a lawyer. I might be too young to be “The Man,” but I probably qualify as “The Man: The Next Generation.” And when I see people dressing in a way that I interpret as a rejection of tradition, I take it as a rejection of the values of civility and courtesy in general. So I dress conservatively, neatly, “properly,” in order to communicate my rejection of their rebellion. They wear their pants halfway down their ass? I put on a tie. They get another tattoo? I get another pair of penny loafers. They rip their jeans? I press my khakis. Each salvo of theirs provokes a retaliatory volley of my own, a war of values fought vicariously through personal appearance. On the one side, order; on the other, chaos.

By this time, some of you might be thinking that I’m a hypocrite. Isn’t it one of the central premises of this blog that clothing ought to be used as a mode of self-expression? Doesn’t that preclude judging people’s clothing choices, and saying that one way of dressing is “better” than another? Why are different styles spoken of as being opposed to one another? Shouldn’t they be allowed to coexist?

But what I’m talking about here is how I conceive of my identity as being bound up with certain social mores, and how I perceive others’ identities (as expressed through their clothing) as being in opposition to (and therefore threatening towards) those mores—and by extension, my own identity. In other words, I’m not saying that these people shouldn’t be free to communicate through what they wear; I just disagree with what they’re saying. The right to express is not debatable, but the merit of the content of that expression certainly is.

Yes, I am making a judgment. Do you disagree? Leave a comment, and let the debate begin.

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.