What to Wear: The Shirt (Part 1)

First, a ground rule: Shirts, like all matter, can be destroyed. A shirt you buy tomorrow won’t last more than two years. Chili cookoffs, leaky pens, poorly-positioned coffee lids... 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, The Editors recommend Seize sur Vingt. And if you're in Bankgok, you can get amazing quality for a fraction of the price from one of the many excellent tailors on Sukhamvit Drive. (The Dread Pirate Robert recommends Lucky & Oscar.)