What’s The Best Men’s Underwear?

Best Men's Underwear
Photo-Illustration: retailers

Much like socks, the best men’s underwear should be comfortable, durable, and stylish (either for you or for someone else who might be looking). Unsurprisingly, men are quite picky about their underwear and many have strong opinions about which style and brand is best. Here, we do not set out to resolve the great brief-versus-boxer debate; instead, we’re featuring some of the best options recommended to us by stylists, fitness professionals, and other discerning and active men across all categories: briefs, boxer briefs, trunks, boxers, and performance underwear for working out and other active pursuits. Read on for the favorite pairs of our 27 cool guys — and, yes, there’s a lot of Calvin Klein, but there are plenty of other options too.

Best boxer briefs

Boxer briefs were the most popular underwear style among the men we spoke to. Of all the pairs we heard about, none received more recommendations than Uniqlo’s simple and affordable supima-cotton pair, which five guys (or six, if you count contributor Chris Black) told us they swear by. One of those guys, photographer Sam Schmieg, says these are even superior to Calvins. “I wore Calvin Klein for a minute, but at this price and comfort level, I can’t pass up Uniqlo,” he says. “They’re soft, breathable, and keep their shape well even after many washes.” Other fans include Malcolm McNeil, a photographer and the content manager at rare-sneaker dealer Flight Club, street-style photographer Christopher Fenimore, menswear brand 3sixteen founder Andrew Chen, and Elliott Foos, formerly the director of coffee at Daymoves in Williamsburg, who adds that “Uniqlo’s basics are unrivaled, and these carry the torch. I’ve been into these for three-plus years (I’ve been re-upping, don’t stress), and I love them.” He personally likes to “keep it classic” with the monochrome black, but notes that “if you feel you need a statement piece, other colors are available.”

Photo: retailer

For a pair of Uniqlo boxer briefs that feel even more barely there than those above, two guys recommend this style from the brand’s AIRism line. Nicolás Lazaro, a community specialist at menswear resale platform Grailed, says he used to wear cotton boxer briefs like the pair above but has “never looked back” since switching to these. “You’ll forget you even have them on,” he says, describing the boxer briefs as “ultralightweight, breathable, and moisture-wicking, with enough stretch for comfort while still providing the necessary support.” Lazaro adds that the underwear dries so quickly he can just handwash and hang dry it overnight if he’s ever in a pinch. Publicist Nick Roberts, the founder of Lawrence & Co., is another fan, telling us they’re “extremely comfortable, and, at $15 apiece, I can stock up knowing I’m getting good quality for the price point.”

While typically more expensive than Uniqlo’s boxer briefs, Calvin Klein’s are as classic as it gets (and, when bought in a multipack, are actually a pretty good deal). This pair, also featured in our list of the best boxer briefs for men, is “exceptional, not too tight, and very low maintenance,” according to Phillip Wong, the co-founder and creative director of men’s skin-care and grooming line Hawthorne. While they come in a plethora of colors, style editor Ian Taylor says sticking with darker tones is your best bet. “Grays and blacks have a bit more of a shelf life,” he explains. “White looks great when it’s 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.”

Photo: retailer

John Januzzi, a product director at men’s clothing brand Bonobos (and the author of How to Wear Socks), told us he’s been wearing these retro-looking boxer briefs for a couple of years and that all his pairs have “held up really well through washes.” That means everything he likes about them has stayed entirely intact, from the “really soft” waistband, to the comfortable seam around the hemline, to the “pretty much perfect length,” which Januzzi says prevents “any of the chafing you might find in a shorter length or a straight-up brief.” He’s not the only Sleepy Jones fan we spoke to: Writer Timothy Latterner describes their boxer briefs as “incredible” and “not unlike Calvin Klein boxer briefs, except the white band and red stripe read a bit preppier.” Latterner adds that he “started off with one pair in black, wore them once, then went and bought 30 more and threw out all the other boxer briefs I had in my dresser.” While he acknowledges that $26 for a single pair is pricey, Latterner promises that they’re worth it (and most guys probably don’t need 30 pairs). “You can’t put a price on good underwear: It’s like eating supermarket sushi for 20 years and then going to omakase in Tokyo.” The fact that we’ve seen these go in and out of stock suggests that even more guys agree.

Photo: retailer

Saxx underwear was mentioned by a few of the guys we spoke with, many of whom noted how much they like the company’s signature supportive pouch. (Celebrities like Chris Carrabba of Dashboard Confessional are also fans of the brand.) Cory Ohlendorf, the editor-in-chief of men’s style platform Valet., told us he’s swears by these “Platinum” boxer briefs. “I’ve tried a lot of underwear over the years, but this is the only brand that ticks all the boxes. They’re thin, supersoft, and yet extremely durable — I can wear them working out or on a ten-hour flight and be completely comfortable the whole time.” That’s because, according to Ohlendorf, the underwear is sewn to mold around your body shape. He’s also a fan of the aforementioned support pouch, which he says “without getting too graphic, means that readjusting is a thing of the past.”

Photo: retailer

In starting his sock brand Kane 11, Peter Hunsinger did a lot of research into what makes a great men’s basic. For underwear, he says he’s “an Under Armour guy,” describing the company’s Boxerjock boxer briefs as “far and away the best” there is. “They have support, they’re stylish, and, most of all, they’re supercomfortable, with a fit that’s second to none,” he says. Hunsinger adds that while he wears the shorter six-inch style most of the time, in the winter he has “a couple of the nine-inch versions for the extra warmth.”

Photo: retailer

Ralph Lauren creative producer Yale Breslin’s favorite boxer briefs also come from an athletic brand. While there’s no reason you couldn’t wear these (or Hunsinger’s Under Armour pair) for working out, the fact that both men told us these are their everyday underwear led us to include them here and not with the best performance underwear further down on this list. Breslin calls his favorite New Balance pair the “perfect boxer brief that makes me feel athletic even when I’m doing absolutely nothing.” Describing the feel as “tight and smooth,” he adds that there’s also “this little pocket that is so unnecessary but makes me feel like a badass at all times. Never know what I’m going to hide!”

Thomas Fortune, the creative director for footwear brand Stubbs & Wootton, is another who favors Calvin Klein boxer briefs, which he has been “wearing since he’s been old enough to remember.” His favorite pair is notably made without cotton, but rather a nylon-and-elastane blend. “The microfiber stretch is perfect for preventing the boxer riding up your leg (the worst) and also allows the skin to breathe.” They’re on the more expensive side, but Fortune promises these are worth it. “They’re very much ‘quality over quantity’ and last for years.”

While more than a few people we spoke to agreed that Calvin Klein is the undisputed “big name” in underwear, we heard about plenty of other classic brands with die-hard fans, too. These all-cotton boxer briefs from Ralph Lauren come recommended by McNeil, who told us that while he likes Uniqlo’s pair, this one is actually his favorite. “In terms of underwear I rock loyally, the G.O.A.T., Ralph Lauren, has always been a daily go-to.” He adds that these check all the boxes, “from fit to comfort” to “the signature waistband.”

Photo: retailer

These affordable boxer briefs come recommended by Sterling Doyle, a senior sales associate at upmarket men’s haberdasher Drake’s, who told us he has come across far pricier pairs that aren’t as good. First sent to him by his mother, the boxer briefs, according to Doyle, are “kind of like the Crocs of underwear; you love to hate them, but at the same time, everyone should have a pair.” That’s because the fit “kind of knocks it out of the park,” he says, describing how they sit above the hip (and have a waistband that keeps them there), don’t “cling-wrap anything” lower down, and never ride up on his thighs. They’re made from a soft, breathable cotton, adds Doyle, who concludes: “All-around, they’re some of the most solid boxer briefs I’ve ever owned.”

Best briefs

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In compiling this selection of men’s underwear, one thing we noticed from our not-scientific-but-still-quite-thorough survey: Stylists tended to prefer briefs. And the clear favorite among all the briefs recommended to us is what many consider the all-time classic of men’s underwear: Calvin Klein’s cotton briefs, recommended by celebrity stylist Neil Cohen, fashion and branding consultant Ronny Opong, barber Mark Miguez, and stylist Brandon Garr (who prefers Calvin’s slightly more revealing Hip Briefs). “I’m a briefs guy,” says Cohen, who likes the style because it doesn’t “ride up” on the leg or “add any extra bulk” when worn with slimmer pants (something thicker boxer briefs can often do). In addition to the fit, Miguez likes that these come in a number of colors. “I like to get a little funky with the loud colors,” he says, explaining that wearing bright underwear “helps my mood on cold winter days in New York.”

Although he’s a fan of Calvin Klein briefs, Garr told us that these Jockey ones are so affordable and comfortable that he’s thinking of ditching his longtime favorite for them. “I came across these Jockey briefs while recently looking for underwear on Amazon,” he says. “They’re 100 percent cotton, and the elastic is just right and hugs nicely without pushing in areas you don’t want it to.”

Photo: retailer

Dolce & Gabbana’s cotton briefs are the go-to underwear for Brian Kelly, a.k.a. the Points Guy, who calls them “super–high quality and stretchy” and “great for sleeping on planes” (being one of the most frequent fliers we know, we’re inclined to take his word for it and have to assume that they’re just as comfortable to sleep in anywhere else). If the price gives you sticker shock, we should note that this set of two breaks down to a more reasonable $27.50 per pair — or roughly the same price as the boxer briefs from (far less storied brand) Sleepy Jones mentioned above.

Cohen also told us about these briefs from Tani, a newer “high-end” underwear brand that he likes a lot. He says the brand “plays with performance fabrics” in an interesting way while still maintaining a stylish and fashionable look. These are made with a patented “Micro Modal AIR” fabric that the company describes as “thinner and softer than silk.”

Photo: retailer

For another luxurious brief, Cohen suggests Tom Ford’s made-in-Italy pair. You’re paying a bit of a premium for the name and the provenance, but you can trust that they’re made to the brand’s exacting standards. These are 95 percent cotton with 5 percent elastane for stretch, which Cohen calls an ideal blend for breathability and comfort. And then of course there’s the sleek design. “They’re very sexy, almost a throwback to a 1970s playboy,” says Cohen, who especially loves all the color options, which includes this shade of deep red.

Best trunks

Trunks are something of a middle-ground between briefs and boxer briefs; they’re essentially boxer briefs with shorter legs, and are a good option for guys who maybe want something a little less revealing than briefs but still streamlined and flattering. Foos pointed us to Calvin Klein’s cotton trunks, which he says have “a bit more structure, which means a bit more security,” adding that “while I’m no Bieber, I certainly feel like I am in these Calvins.”

Photo: retailer

Tommy John is another brand that got a lot of love in our roundup of the best boxer briefs for men, with guys praising its underwear’s design and high-quality fabrics. Barron Cuadro, the founding editor of Effortless Gent, wears the company’s Titanium Trunk, which is made from a blend of micro-modal and Spandex for stretch. “The modal blend is supersoft, comfortable, and relatively quick drying,” he says, adding these “just feel great when you have them on.” Adding to their comfort is a “nice and wide” waistband, according to Cuadro.

Best boxers

The guys we spoke with tend to like cotton boxers for sleeping or loungewear (and they tend to prefer something slimmer and more supportive while out and about every day). Two told us their favorite boxer comes from upmarket British brand Sunspel, which makes other basics that stylish guys swear by. “The only time I would venture away from Calvin is for Sunspel’s cotton boxer shorts,” says Fortune. “However these would only be for sleeping.” Menswear consultant Nick Wooster is also a fan of Sunspel’s boxers, particularly this Oxford-blue color. As Wooster puts it, “What’s better than a periwinkle shirting fabric in a boxer short?” Going against the grain, he likes to wear these with pants, specifically with “drop-crotch and pleated pants.”

Photo: retailer

For a more affordable boxer, Cohen likes this pair from J.Crew. “I just wear them for sleep, but some guys still wear them [as underwear],” Cohen says of the brand’s cotton boxers, which come in a variety of fun prints. “They’re really well-priced,” he says, adding that the 100 percent cotton fabric “has a nice hand.”

Best performance underwear

When it comes to performance underwear, Lululemon’s is recommended by two fitness pros: Dominic Mangine, a founding coach of rowing studio Rowgatta, and master personal trainer Ariel Brill. “Lululemon has great products,” according to Mangine, who says this pair of boxer briefs is “an awesome option for training because of the comfortable fit and sweat-wicking fabric.”

This Saxx pair, made from a high-tech mesh fabric with activewear in mind, are the choice of personal trainer Sean Sewell, who runs the gear-review site Engearment and the online-fitness program Mountain Fitness School. Sewell says they’re “very comfortable and not compression-feeling at all,” making them also suitable for wear “under a suit and under jeans for date nights.” Strategist contributor Steven John also swears by Saxx boxer briefs, especially on long runs, when he says their supportive pouch “reduces chafing and provides even more surface area to wick moisture from.”

Photo: retailer

While Brill is a fan of Lululemon, he says these more affordable Reebok boxer briefs are his go-to for workouts. Made from a blend featuring 92 percent polyester (a fabric often found in performance underwear due to its sweat-wicking abilities), and 8 percent elastane for stretch, he says that “they’re flexible and supportive for all gym activities.”

Another brand known for its underwear made with technical fabrics is ExOfficio, which counts Cuadro as a fan. He told us the material of these is not only “super-breathable,” but also “dries really quickly,” making them a great choice for travel or outdoorsy pursuits like camping, when “you need to wash and hang dry” underwear. “Overall, they’re really comfortable,” he adds.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best men’s wardrobe basics, white T-shirts for men, jeans for men, white sneakers for men, and flattering clothes for men. We update links when possible, but note that deals can expire and all prices are subject to change.

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