Much like socks, the best 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 active men across all categories: briefs, boxer briefs, trunks, boxers, and performance underwear for working out and other active pursuits. Read on for all the 17 pairs recommended by our 15 cool guys. (Yes, there’s a lot of Calvin Klein, but there are plenty of other options too.)
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 three guys (or four, if you count our columnist 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 marketing manager at rare-sneaker dealer Flight Club, and Elliott Foos, the director of coffee at Daymoves in Williamsburg, who adds that “Uniqlo’s basics are unrivaled, and these carry the torch. I’ve been in 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.”
While certainly 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, Ian Taylor, the London-based editor-in-chief of men’s style site FashionBeans, 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.”
For something even simpler than the Uniqlo boxer briefs, Tim Melidio, the founder of men’s fashion site Stay Classic, likes these cotton boxer briefs from Hanes. At $14 for a five-pack, they’re also an even better bulk deal than the above Calvins.
Thomas Fortune, the creative director for footwear brand Stubbs & Wootton, also 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 with 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.”
Pretty much everyone we spoke with agreed that Calvin Klein is the undisputed “big name” in underwear, but we heard about plenty of other brands with diehard 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, importantly, “the signature waistband.”
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, 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).
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 long-time 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.”
Cohen also mentioned 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.”
For a “luxury” 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 1970’s playboy,” says Cohen, who especially loves all the color options, which include six “shades of nude.”
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.”
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 “micromodal” and spandex for stretch. “The modal blend is super soft and comfortable (also relatively quick drying) and just feels great when you have them on,” he told us, noting that “the band is nice and wide which also adds to the comfort level.”
The guys we spoke with tend to like cotton boxers for sleep or loungewear (they prefer something slimmer and more supportive for everyday wear while out and about). “I just wear them for sleep, but some guys still wear them [as underwear],” Cohen says of the cotton boxers from J.Crew, which come in a variety of fun prints. “They’re really well-priced,” he explains, adding that the 100-percent-cotton fabric “has a nice hand.”
“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 pair, which, in addition to stripes, comes in solid shades of white and light blue. 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.”
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.”
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.”
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. This pair, made from a high-tech mesh fabric, is designed with activewear in mind, but personal trainer Sean Sewell — who runs the gear-review site Engearment and the online-fitness program Mountain Fitness School — told us they’re also great for “non-sport use.” He’s worn them “under a suit and with business casual often, and under jeans for date nights” and says they’re “very comfortable and not compression-feeling at all.”
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 outdoors-y pursuits like camping, when “you need to wash and hang dry” underwear. “Overall, they’re really comfortable,” he adds.
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