Combining the snug fit of briefs with the coverage of boxers, the boxer brief, for many men, represents the best of both worlds. They were invented in the early 1990s by designer John Varvatos, who was then at Calvin Klein. Varvatos cut a pair of long johns and managed to create what is 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. To sort through all the options, we asked 11 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 suggests avoiding the Marky Mark look, instead going 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.” Phillip Wong, co-founder and creative director of Hawthorne swears by these, too: “I’ve worn only the classic Calvin Klein boxer briefs for as long as I can remember. The shape is exceptional, not too tight, and it’s very low maintenance,” he says.
Although the Calvin Kleins are Wong’s favorite, he says these boxer briefs from Everlane deserve an honorable mention. “The longer legs hug your thighs more, so there’s less of the bunch-up and movement you sometimes get with shorter boxer briefs,” explains Wong, who also appreciates their high-quality fabric. “They’re almost completely Supima cotton, and very lightweight.”
For something fun and easier on the wallet, fashion and branding consultant Ronny Opong likes these boxer briefs from Urban Outfitters. “Surprisingly, they make some great boxer briefs,” he says. He likes the zebra print, but if you’re feeling less bold, the same style is also available in solid black. You can buy a single pair for $12 or a three-pack for $28.
Tim Melideo, who runs Stay Classic, a men’s fashion site focused on finding more affordable and stylish options, swears by Hanes cotton boxer briefs. They’re simple and inexpensive, and they last.
This luxury option from a newer brand is 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 them, and it’s moisture-wicking, which, for this kind of garment, is very important.”
They’re pricier than standard boxer briefs, but Taylor loves the high-quality jersey material in Sunspel underwear.
Underwear start-up Tommy John got a lot of love from our panel, with three people recommending a different style from the brand. Derek Guy is a big fan of their “Second Skin” model, and he especially likes the micro-modal fabric the company uses. “The non-pilling blend wicks moisture away from the skin better than pure cotton, which means you feel drier and more comfortable throughout the day,” he says. The company designs their underwear with a unique, horizontal “quick draw” fly. “I was skeptical when I first heard about it,” says Megan Collins, founder of menswear site Style Girlfriend. “Like, how much better can that really be? 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.”
Stylist Brandon Garr generally prefers traditional briefs to boxer briefs because he finds them more comfortable, but the one pair he’ll make an exception for are these modal boxer briefs from Emporio Armani. “They feel like a second skin, and don’t bunch up like most boxer briefs,” he says.
“I purchased my first pair of SAXX brand men’s underwear four years ago, and I haven’t worn anything else since,” says Kyle Andrew, an actor and model. He appreciates Saxx’s “ballpark pouch” design, which he says “keeps things separated for maximum comfort.” His favorite style is the Ultra boxer briefs. They’re made primarily of viscose fabric, a moisture-wicking cotton alternative similar to modal.
Melideo says he generally prefers something less expensive that he can buy in bulk, but “I did get a couple of pairs of MeUndies,” he says, referring to the direct-to-consumer brand. “They are SUPER soft.” À la carte they’re $24 per pair, which is comparable with most premium brands. But if you sign up for the company’s monthly subscription service that price drops to $16.
Cassandra Sethi, New York City–based personal stylist and founder of Next Level Wardrobe, is a fan of another underwear start-up, Mack Wheldon. “In my past life as a senior buyer for a luxury fitness gym, our clients loved Mack Weldon. I’m a fan as well. They are based in NYC, develop their own amazing fabrics and are experts at fit as well as quality. I highly recommend their Airknit fabric. It’s super lightweight and breathable with four-way stretch.”
Barron Cuadro, founding editor of Effortless Gent, also recommends Tommy John, but he prefers this trunk-style model which has a shorter leg than the boxer-briefs. He loves this pair for the fit, wide waistband, and “ultrasoft” fabric. And unlike with other underwear, he hasn’t seen any pilling in them over the course of many wears and washes.
Collins recommends Pair of Thieves as 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.” The bold prints add some punch to a dull underwear drawer, and two-packs go for less than the price of a single pair from higher-end brands.
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