On 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.


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.