Dress Better This Holiday Season (Advanced Edition)

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.