Sometimes the things seen least matter most. This is the case for underclothes. Hence the adage, “Hold your friends close and your underwear closer.” Whether you patronize any of the classic double-named establishments on Jermyn Street—New & Lingwood is a favorite—or stay closer to home, the closest thing to your body shouldn’t be an embarrassment. (It probably shouldn’t be featured in a television advertisement either.)
Classic boxers come in patterns that tailors use for their shirts—pinstripes, checks, solids—and you can’t really go wrong with any. Turnbull & Asser, the English mainstay which makes Prince Charles’s shirts, offers Egyptian cotton shorts that are worthy of any man. Their signature “tunnel” waistband, where the elastic is threaded through fabric as opposed to being sewn on the waist itself, means you don’t feel it against your skin. The result is great comfort, and, naturally, it comes at a great price (upwards of 35 pounds sterling). But you can find good boxers for much less, some with mother of pearl buttons. Is that excessive? Not if they last you five years.
Others prefer boxer briefs. In fact, a recent survey showed 67% of women prefer them on you. A boxer brief combines the support of a brief with the freedom of a boxer. For their popularity, we have Marky Mark and his Calvin Klein adverts circa 1990 to thank. Most luxury companies that make boxers also tighten them a bit to present boxer briefs, too. You’ll probably want to forego loud checks and pinstripes here and stick with solids wrought in Egyptian cotton with a touch of Elastan for tightness. Schiesser, a 125-year old German company, makes a very handsome pair with gusseted seams, generous pouch and no shrinkage.
You can, of course, also seek out novelty underwear—but is that a region you want to be the source of mirth for others?