Combining the snug fit of the brief with the coverage of a boxer, the boxer brief for many men represents the best of both worlds. Invented in the early 1990s, the underwear came to be when designer John Varvatos, then at Calvin Klein, cut a pair of long johns and created the new style, now the most popular kind of underwear for men.
“They’re infinitely better than boxers,” says Derek Guy, editor at men’s style site Put This On and blogger at Die, Workwear. “They give you support; they don’t bunch up in your pants. And when they’re made from good materials, they just feel nice.” Today, there are hundreds of styles of boxer briefs to choose from. Since it’s Underwear Week here at the Strategist, we asked five menswear experts which ones are the best.
The original Calvin Klein style is still one of the best out there, according to Ian Taylor, the London-based editor-in-chief of men’s style site FashionBeans. He cautions, though, to avoid the Marky Mark look and go with a darker color like gray or black. “In photo shoots, you often see people wearing white, which looks great when it’s well-lit and photographed on a model with a six-pack, but if you’ve been wearing them for six months, they won’t look quite as pristine. Grays and blacks have a bit more of a shelf life.”
A luxury option from a newer brand, this style from Hamilton and Hare are also one of Taylor’s favorites. He says the British company is “doing loungewear and underwear better than anyone else at the moment. There’s a softness and comfort to their jersey material, and it’s moisture-wicking, which, for this kind of garment, is very important.”
Underwear start-up Tommy John got a lot of love from our experts. Barron Cuadro, founding editor of Effortless Gent, loves this pair for the fit, wide waistband, and “ultrasoft” fabric. Unlike other underwear, he hasn’t seen any pilling in these boxer briefs over the course of many wears and washes.
Derek Guy is also a big fan of Tommy John, especially their Second Skin model. “Made from a non-pilling micro-modal blend, it wicks moisture away from the skin better than pure cotton, which means you feel drier and more comfortable throughout the day,” he says.
As founder of menswear site Style Girlfriend, Megan Collins says guys “often feel compelled to share with me their own personal underwear journeys.” Since she hears a lot about men’s underwear, she wasn’t initially impressed by the new, horizontal “quick draw” fly design on Tommy John boxer briefs. “I was skeptical when I first heard about it. Like, How much better can that really be?” she says. “But then I gave a pair to my best friend’s husband to try out, and to this day he still will text me saying how much he loves them.” They’re now one of her top picks for guys looking to splurge a bit on their underwear.
For a budget pick, Collins recommends Pair of Thieves, one of the few direct-to-consumer brands available at budget prices. “Even though they’re more of a mass brand, they really do make it part of their DNA to provide the same level of — I don’t know — underwear technology that we’ve come to expect from other companies that are out there ‘disrupting’ the underwear space, as it were. The geometric prints add some punch to a dull underwear drawer, and the three-packs go for less than the price of a single pair from higher-end brands.
Scandi minimalism meets underwear in these simple, affordable boxer briefs from Swedish brand Bread and Boxers — a favorite of Isaac Hindin-Miller, a DJ and author of menswear blog Isaac Likes. “They’re a clean and minimal design — no logos — super comfortable, great short length, and they’re well-priced,” he says.
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