The Best Men’s Underwear for Every Conceivable Situation

Your underwear drawer could use a makeover. We're here for you.

Updated December 8, 2020 8:42 am
The Best Men's Underwear for Every Situation

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It’s easy, living in a modern menswear wonderland of slub hemp tees, Japanese denim and blanket-lined shirt jackets, to forget about the basics underneath. But your undergarments, especially men’s underwear, are well worth your attention — and cash.

Longtime powerhouses Fruit of the Loom (168-years-old) and Hanes (119-years-old) are still kicking it, and still fill the bottom drawers of many a Baby Boomer’s nightstand, but lately, younger, hungrier brands like Mack Weldon, Tommy John, and Saxx have entered the men’s underwear space, selling briefs and trunks with silver threading, hammock-inspired pouches, and “stay-put” technology.

These advancements in men’s underwear have also brought us to an important conclusion: if you’re running and sleeping in the same pair of skivvies, you’re doing yourself a disservice. Your drawer should be a diverse group, with technical options for a range of use cases. Which is why we recently spent a few weeks testing 10 different pairs, and decided on the situation each would thrive in. Below, find a pair for everything from flights to date night, plus our favorite overall boxer brief, which will serve you well for just about any activity.

Mack Weldon Silver Trunk Men's Underwear

THE BEST OVERALL: Mack Weldon Silver Trunk

Believe the hype. Mack Weldon makes our favorite undergarments. I picked up two pairs of the Silver Trunk late last year and have looked forward to laundry day ever since, so eager am I to get them back into the daily rotation. Mack Weldon’s been around since 2012, and operates similar to an athleisure company, but with a heightened focus on function. They churn out elevated basics using unparalleled materials. The Silver Trunk is a Supima cotton/polyester/lycra blend, enmeshed with an antimicrobial silver threading that repels odor and keeps the fabric fresh with repeated uses. NASA uses it, Olympic athletes wear it, you need to feel it for yourself. This pair of briefs sit tight on the thigh (hence the “trunk” title), so we’d recommend it for workdays or working out. But they’re so goddamn comfortable that you can really wear them whenever for whatever.

Tommy John Second Skin Trunk Underwear

FOR THE 9-TO-5: Tommy John Second Skin Trunk

Tommy John is another new brand in the men’s underwear space. Husband-wife team Tom Patterson and Erin Fujimoto quit their jobs to design an undershirt that stayed tucked back in 2008, and these days the brand sells an extensive line of serviceable, stylish everyday essentials, including socks, polos and hoodies. But we’re here for their boxer brief. We tested out the Second Skin Trunk. The inseam here is only 4.5″, but this company is clearly committed to garments that don’t annoy. During long days at work, these guys never bunched or pinched, and the rayon/spandex blend is as comfortable as it is flexible. Wear these to work and settle in.

Texere Bamboo Boxer Shorts Men's Underwear

FOR SLEEPING: Chill Boys Bamboo Boxer Shorts

From Dr. Maria Sophocles, who spoke to us earlier this year on fertility: “It’s all about heat. Tighter men’s underwear/pants mean the testicles are closer to the body which means they are warmer. That’s not to say don’t wear form-fitting things; it just means be aware and take breaks (like sleeping naked or in something loose fitting).” If you’re not sleeping in the nude, which obviously isn’t for everyone, you need a pair of flowy, unobtrusive briefs. If you feel like a grandpa when you put them on, you’re on the right track. I like this pair from Chill Boys, which is made with bamboo viscose — an absorbent, sustainable material that self-regulates its temperature. Also, these are tagless, which I appreciated.

Saxx Underwear Sport Mesh Men's Underwear

FOR THE GYM: Saxx Underwear Sport Mesh

Skip the mesh shorts from Under Armour or Nike. Their underwear is an in-house afterthought. Saxx, meanwhile, was literally founded on the concept of preventing chafing, back in the late aughts. The founder, Trent Kitsch, invented a hammock-shaped “ballpark pouch” meant to reduce the floating around (and subsequent friction) of your parts down there. I’ve worn them for lifts, cardio, jump roping, you name it, and Saxx is the real deal.

Flint and Tinder Heritage Brief

FOR WEEKENDS AWAY: Flint and Tinder Heritage Brief

Flint and Tinder is Huckberry’s workwear brand, and you’re probably used to us writing about their waxed trucker jackets and Henleys. But the brand makes a mean pair of boxer briefs, too. The Heritage Brief sits about a third of the way down the thigh and is knit, cut, sewn, dyed, and washed with 95% organic cotton in Los Angeles. If you’ve worn an organic cotton tee on your shoulders, just wait until it’s hugging an area that really counts. We like these for travel; Flint and Tinder ethos is big on getting out there and after it … these will serve you well on flights, road trips, cross-continental motorcycle adventures, etc.

Tommy Bahama Woven Boxers

FOR THE COUCH: Tommy Bahama Woven Boxers

Tommy Bahama’s business plan — get average-sized, normal guys to wear Big and Tall Hawaiian shorts as often as possible — is goofy, but I’ve been beating the drum on their loungewear for a long time. They make some of the best Sunday afternoon gear in the game, and that extends to their woven boxers. I’ve worn them on the couch, to bed, and to the grocery store for four or five years, and they only get softer. Not to mention, the designs are fun and different after wearing self-serious monochromatic undergarments 90% of the time.

Hanro Micro Touch Men's Underwear

FOR DATE NIGHT: Hanro Micro Touch

Hanro is a Swiss brand that specializes in luxurious sleepwear. Their briefs are on the pricier end of the spectrum, about as expensive as a pair of canvas sneakers, but you only need one pair. Christen ’em your “night out pair” for special occasions with your significant other. These men’s underwear are as much for your better half as they are for you — they’re constructed from a sleek microfiber, and feature a “seamless rear,” which will apparently make your posterior look great. Only one way to find out.

Smartwool Merino 150 Printed Boxer Brief

FOR HIKING: Smartwool Merino 150 Printed Boxer Brief

These are the real deal. Smartwool’s been looking to branch out its offerings beyond socks in the last few years, and their Merino briefs are a worthy addition to the collection. I wore these during an arduous seven-mile hike through Yosemite back in June, that saw us walk through multiple waterfalls. The Merino is an unfamiliar feel down there, but in a good way. Huge points on breathability, fit, anti-chafing capabilities. As I’m not barnstorming National Parks every weekend, I also wear them casually for runs and workouts, where they excel as well.

Calvin Klein Boxer Briefs

FOR THE COST-CONSCIOUS: Calvin Klein Boxer Briefs

The nether-regions’ resident Chuck Taylors. Calvin Kleins are about as iconic as men’s underwear is going to get, and the quality’s still decent enough to back it up. I love them as a bulk option from Nordstrom Rack, which pretty consistently offers a pack of three for $20. Consider ordering a size up, though, because, with repeated washes, they will definitely shrink a bit. (100% cotton probz.)

J.Crew Knit Boxer Briefs

FOR PHIL DUNPHY DADS: J.Crew Knit Boxer Briefs

True story: I forgot to pack a pair of boxer briefs for the day last week, on the same morning I wore lined gym-shorts to my workout. Mayday. After an unconscionably uncomfortable morning of wearing gym shorts under a pair of jeans, I went to a nearby J.Crew during lunch to pick up a pair of “rescue briefs.” Feeling buoyed by the end of my torture, I went for a whimsical pair: these knit boxer briefs which are covered in pizzas. Every man should have a couple of silly boxers, if only to remind himself first thing in the morning to not take life so seriously. Plus, they’re comfy and true to size.

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