Part 2, Dress Shirts

They all came, some wore sentiments
Emblazoned on T-shirts, proclaiming the lateness
Of the hour, and indeed the sun slanted its rays
Through branches of Norfolk Island pine as though
Politely clearing its throat…
—John Ashbery, “The Other Tradition”

Sweet, lovely shirts. Barrel-cuffed or French, button-collar or fly, we’ll take them in any form—as long as they’re well made. Unfortunately, as we grow older, our styles age with us, and a line of bent hangers marks our sartorial missteps. Here then are some rules to help you grow your battery of shirts with care.

First, a ground rule: Shirts, like all matter, can be destroyed. A shirt you buy tomorrow won’t last more than two years. Chili parties, leaky pens, sip-tops, the world is full of ways to ruin good fabrics. So don’t get sentimental when your Thomas Pink turns pinot noir; you never should have spent that much money anyway.

For dress shirts, you’ll either buy them off the rack or have them made for you. While the latter is the preferable method, it’s also usually the most expensive. Most men buy dress shirts in three ways: from a catalog, off a hanger, or from those wooden cubby-holes that haberdashers use to make their store seem like a gentleman’s club.

In all cases, the most important thing to know is your size. We don’t mean small, medium, or large. We mean knowing the length of your arms and the girth of your neck at all times. If you don’t know, go to a fancy shirt-shop and have a caring salesman wrap you with measuring tape. Scribble down the numbers and memorize them as if they were a pass-code to a better life. And they are.

This pass-code, however, is not a universal standard (except that any man in a well-fitted shirt is probably living better than a man in an ill-fitting one). Neck and sleeve sizes don’t mandate design, so where one 15-33 makes you look like Justin Timberlake, others could drape Perry Mason. Some shirts are cut longer than others so you have enough tail to tuck. Unfortunately, most times you’ll look like you’ve crapped a blanket. Others are cut too short, so when you raise a hand your tail comes un-tucked. This is why we don’t recommend catalog shopping where avoidable; you need to sample the wares before clinching the sale.

And sampling means noticing how the shirt is made. Examine the stitching, the buttons, the hem. If the shirt looks cheap, it is. And if you wear that shirt, you’ll look cheap. If looking cheap is your thing, God save you. Shirts, while more expendable than suits, are worth the money they cost, to a point. No shirt, unless it’s made-to-measure, is worth more than $150. If you’re going to spend more than that, have it made for your body.

Let us note, before going further, that the experience of having good shirts made for your body, with all of your preferences in mind—style, collar, cuff—is a wonderful, expensive indulgence. You are choosing to pamper your vanity rather than a small village in Africa. You must be without guilt or illusions: you are paying someone a lot of money to make shirts that will fit you, and only you, perfectly. If you decide to go down this path, make sure you work with a good tailor, and have the permission of your partner. If you’re in New York, may we recommend Seize sur Vingt.

To start with style, there are a variety of collars available to the shirt-shopping man.

Straight: Possibly the most standard of men’s collars these days. This collar aims in varying degrees of “down.” There are a number of “spreads” available in straight collars, the “spread” being the amount of space visible between the collars, at the neck, where a tie might live. Choose too-narrow a spread and you could be on the GoodFellas poster.

Spread: A straight collar that’s been spread to the point of not being considered straight anymore. This collar is also sometimes referred to as the “cutaway” collar, for the large amount of visible space between collar tips; it’s also called the “British Spread,” because it’s popular there and Americans love wearing anything that smells European. Due to their construction, spread collars are typically slightly less-wide than straight collars. This collar, too, is available in a variety of spread distances.

Button-Down: The collar that’s affixed to the shirt, popular with Mormons, prep schools, mod parties, and consulting firms. I.e., either hip or square, depending on how you wear it. Never wear the collar unbuttoned. And don’t snip off the buttons to make it a non-button-down shirt: you’ll still be left with buttonholes in the collar, and people will notice. And we don’t want that.

Curved: A straight collar that has a slight curve outwards from the face. It’s a different look, for a different type of man. Yes, just different. And sometimes preferred by Steve Martin. No comment.

Tab: A collar that has a small snap-tab connecting the two collar sides together. No real idea what this tab is for. Must be a reason. Maybe it’s an added security feature.

Banded: Quite simply, no collar—just a button at the neck. Preferred by Michael Stipe circa-1990 and Robin Williams at any formal event. Come to think of it, Steve Martin’s also worn it on occasion. Good for wooing women with the I-used-to-be-a-Yoga-instructor-but-now-I-study-African-drumming look.

The point in having so many collars is that you get to choose one that suits you. It’s often said that men with narrow faces should choose collars that are wider, to help broaden their faces; conversely, men with wider faces should choose collars that are narrower, to help lengthen their faces. Personal style is really the best route, though: don’t choose a collar that isn’t you. And don’t blame your face for keeping you from wearing what you want. Only Hugh Grant is Hugh Grant, and anyway, we suspect he’s a doofus.

On to cuffs. This is the easy part. You have a few options, but it’s mainly built-in buttons or holes for cuff-links. Again, personal style. A note on cuff-links, though, in case you want to wear them: never wear cuff-links if you’re not wearing a jacket. Otherwise you’ll look like a pirate who forgot to hide his treasure.

Once you have your cuffs, size, and collar set, you’re left to fit and color. If you can wear them, always opt for a “fitted“ or “athletic” style dress shirt. This means you’ll walk away with a garment that tapers toward your waist, as opposed to the kind that billows at your back like a galleon at full sail. A well-fitted shirt will look like it was sewn right on you. Except without the drops of blood.

Finally: color or pattern. Men usually choose according to one of a few reasons: either they trust the color (men whose shirts are all either white or blue), they need some new colors (the men we just mentioned who are now sick of white and blue), or a color has become trendy (1999, Banana Republic, crimson red). Again, the most we can say is choose the style that’s right for your look, but don’t be afraid of expanding your repertoire. Remember: Shirts are where you get to have the most fun with your outfit, and it’s so easy to be boring.

But what about the sleeves? Good point. For places with summers in the mid-nineties, you can get away with long sleeves for most of the year. And don’t be afraid to roll those sleeves up when necessary. Not only does it look great, but it also suggests you’ve been hard at work on something or other. Probably.

If, however, your summers sit in a neighborhood that’s no stranger to breaking 105 degrees, feel free to wear your dress sleeves short and sit sweat-free, knowing fashion didn’t give you two weeks of carefully tended re-hydration therapy in the hospital.

Now you have your shirt, and you’re ready to get dressed. What seems to change most in dress shirt fashion is how to wear them. Right now it’s alright to leave the tail un-tucked (unless you’re wearing a suit) assuming the shirt tapers to the waist and ends before it’s half-way down your ass. Still, with the un-tucked look so pervasive, tucking or not tucking doesn’t say much, assuming you don’t look like a slob. What people really want to know is, how many buttons are unbuttoned at the top of your shirt.

Zero buttons? You’re either a) the classic nerd, b) an out-of-touch New Waver, or c) a turn-of-the-century heartland obsessive. In all cases, buy a tie; you’ll do yourself a world of good.

One button? Average. Simple. No judgments to be made here. You’re not offending anyone; you’re making nobody wonder. This is probably good.

Two buttons? If you’re starting each day this way, you’re either a cocky bastard or European, and lucky for you, we admire both types. For an American, though, it’s worth waiting until after lunch before you slip that second button.

Three or more buttons? Hope you’ve got another shirt on underneath there, Rico Suave.

Now you’ve got your shirts, you’re wearing them, and people love you. At some point, though, you need to take them off. When it comes time for cleaning, the best method is hand-washing, followed by a nice, stiff press. But who’s got time for that? Instead, get them dry-cleaned (no starch) or have them cleaned and pressed.

When they get back from the cleaners, call that special someone, make drinks, lay a fire. Escort your lover to the closet and—slowly!—take down each shirt, unbuttoning every cuff (you can use your teeth), then throw them up so the air is a cloud of stripes, an ecstasy of cotton.

We love good shirts.