The Best Men's Underwear, According to Menswear Experts

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SPY consulted with designers and stylists to see which men's underwear is worth purchasing and wearing daily.
Uniqlo makes really thoughtful, quality products, but affordable ones, too. These $15 boxer briefs are made with the Japanese retailer’s proprietary AIRism technology, which makes them super breathable, keeping you dry and cool. The knit construction creates a woven effect, helping to ensure they don’t fray and break down over repeated wears — so you can snag a few pairs at once without being concerned about having to pitch them two weeks later. “I’m a man of loyalty — if it ain’t broke, I don’t fix it,” said Appugliesi. “The AIRism Boxer Briefs from Uniqlo are the only undies a guy can ask for, and they have matched function and price very well.” The high-quality, feature-rich design (which feels weird to say about briefs, but here we are!) makes it a pair of underwear that punches well above its weight. Once you add in the price, it’s hard to argue with — and this pair handily wins our best overall pick for men’s underwear.
Fresh Clean Threads’ Black Boxer Briefs are made with luxe silky micro modal fabric that provides a smooth fit and enough support for comfortable all-day wear. They’re engineered with a waistband that sits snug without rolling or bunching up, and the stretchy spandex helps each pair fit comfortably on different body types. They’re breathable enough for workouts and travel but durable enough to be an everyday go-to for the office as well. At $18 a pair, they’re not prohibitively expensive and easy to stock up on, but also don’t feel like they’re bought in bulk making them our runner-up pick.
Why It Stands Out: The comfort! “These feel like a soft t-shirt [against my skin] and don’t hug my waist too tight, which is the most important thing to me,” said Hayes. “The waistband is seamless instead of an elastic band, which I find more comfortable.” Made For: Those who don’t like boxer briefs. “The tightness of [boxer briefs] makes them slide off me sometimes when I bend over, and I don’t really want to be worrying about plumbers crack in the office,” said Hayes. ROI: Super soft boxers that are absolutely worth more than their $18 price, thanks to higher quality construction, materials, and features.
Why It Stands Out: Sometimes, the brand name isn’t worth it — but that’s not the case with Calvin Klein. Made immortal in Back to the Future and their famous ad campaigns, the ol’ CK remains a mainstay in the underwear world because they’re comfortable, rarely ride up, and (let’s face it) remain cool. Made For: The Creature of Habit,” per Corrigan. “You can't go wrong here, they will never let you down. Get one for every color of the week.” ROI: The cotton stretch version is extra soft and even includes a bit of moisture-wicking material to keep you from overheating.
Why It Stands Out: “Support and breathability are crucial in this category,” said Corrigan. “Your lower half will certainly thank you for making this decision after your next intense workout.” Made For: Guys who want more of a brief feel during their workouts instead of a compression short feel — while still getting that sweet, moisture-wicking feeling. ROI: Adidas’ performance mesh boxers are constructed from a polyester and elastane blend with mesh (including in the crotch) to make your workouts a little easier down under. The only “riding” that’ll happen is what you do on the exercise bike, as these briefs are designed to not ride up no matter the activity. Plus, since these come in a three-pack, most of your gym visits will be covered with one purchase.
Why It Stands Out: “The Merino Boxer offers superior comfort and moisture management to keep all things sweaty and swampy from ruining your day,” said Corrigan. Made For: The Merino wool construction means these boxers actively wick moisture away from your body, which means you can use them for, well, pretty much anything. Whether it’s high-sweat activities like hiking or even just wearing them under your clothes during a commute, they’re suited for just about anything. ROI: While they’re a little pricey, the wool construction keeps you comfortable, odor odor-free, and makes them more than worth their price. In other words, they’re worth every penny.
Why It Stands Out: Just like the pack of Pokemon trading cards you used to get as a kid, you don’t know what patterns will be on each of the three different kinds of briefs from MeUndies. It’s a fun and surprising way to change your underwear rotation. Made For: “Adult life doesn't bring many style surprises, which make these mystery packs that much more fun,” said Corrigan. “Who doesn't want a little throwback to the days of wearing Scooby Doo or a fun bold pattern under your shorts? ROI: You’re getting three briefs for less than $20 per pair, and they’re all crafted from the MicroModal that’s soft, flexible, and super comfortable above all else.
Why It Stands Out: The perfect intersection of money and quality, with a strikingly branded three-pack of Armani briefs. Made For: Those who want real good, long-lasting, and quality underwear all at once without having to pay a ton to get it. You’ll get three pairs for about $18 a piece that are trendy and fit every part of you really well. ROI: “Hear me out: while $54 for a pack of 3 might feel outrageous, you know that the fit will be impeccable, the quality will be top-notch, and they might just give you that extra spring in your step,” said Corrigan.
Why It Stands Out: These are quality boxer briefs that you can likely grab from your local mall at a steep discount. Made For: The skeptics who don’t believe you can get good underwear from mall brands, Jake Woolf totes these as his go-tos and sent a frantic dispatch about them during Fashion Week to us. With regard to them being on sale, he stated he was “kinda shook” about how “not very available” some of the colorways were. ROI: The soft cotton spandex with a brushed waistband makes them really comfortable and cozy. Also, there’s very rarely a reason to buy a basic at full price from a retailer like J.Crew. They’re almost always having a sale, so if this product isn’t currently discounted wait a week or so and chances are it will be.