8 Best Boxers For Men: Making an Under-Statement

I remember my grandmother telling me to always make sure to wear clean underwear. “You never know if you’ll be in an accident,” she said. As I grew up, it stuck with me. I mean, of course, you should wear fresh underwear every single day. This is non-negotiable. But you should also always wear your favorite pair.

In the end, we dress for confidence, and everything we put on every day should only help that case. Your underwear is no different. Honestly, the fact that only you know what you’re wearing can add a little je ne sais quoi to your step.

The number one thing that helps our confidence is comfort. Nothing ruins a day like an uncomfortable pair of underwear. So, what exactly makes the best boxers for men? Is it the fabric, the fit, the length? The truth is, all of these details matter, and with all of our different lives and daily needs, it wouldn’t be fair to call just one pair of boxers “the best.” Below, we delve into a few different factors involved in picking the best boxers and present our eight favorites.

What to look for in a pair of boxers

Most men should probably own at least a few of each style. (And if you’re interested in having some briefs and trunks in the mix, check out our list of Best Briefs.) A nice pair of traditional woven boxer shorts is clutch when wearing a looser fitting chino pant or shorts. When wearing jeans, often you’ll need boxer briefs that won’t ride up your legs, leaving you “adjusting” nonstop throughout the day.

If you’re very active, you definitely want some more technical sport boxers in your mix. These also come in different styles. A few amazing action sports companies have developed new styles with “pouches,” which help keep everything in place, and the bigger companies have taken note and many are now offering similar constructions.

It’s hard to pin-point the best material for boxers. With so much attention to men’s grooming, self-care and fashion, it’s no wonder we have seen so many innovations in the underwear market. And most of these innovations start with fabric. Of course, knit and woven cotton still dominate the market, but we have so much more choice today. Micro modal is super soft and comfortable, and way more sustainable than cotton. Supima adds moisture-wicking and anti-stink properties, and, of course, silk will leave you feeling special all day long. The options seem endless, but our curated selection of the eight best boxers for men is truly the crème de la crème of what’s on the market today.

The 8 Best Boxers in 2021

BN3TH breathe infinite iconic boxer in ash grey

Best Snug Fit: Bn3th Infinite Ionic

I’ve been a fan of Bn3th (pronounced “Beneath”) since day one. The trademarked MyPakage Pouch Technology was one of the first on the market and is still the best available today. Bn3th was born out of skateboarding and has always kept their emphasis on active lifestyles, so, of course, they offer an array of cool colors and patterns to really stand out. These briefs are built for athletes, so most of their styles offer moisture-wicking properties and different lengths of briefs for different activities. 

The Infinite Ionic features groundbreaking IONIC+™  No Stink Technology and, let me tell you, this is no joke. A permanent silver strand is weaved into their modal to kill stink before it starts by preventing the growth of odor-causing bacteria. And the best part? Because it’s not a spray or coating and is actually weaved in, it never wears out. As their saying goes, Bn3th “feels like Sunday, grinds like Monday.”

Everlane Uniform Boxer Brief

Best Minimalist: Everlane Uniform Boxer Brief

Every once in a while, a brand flips the norm and leaves us thinking, It’s about time. Why didn’t anyone do this before? And usually, it’s a not a gigantic change but a small detail. Like not putting a logo on a men’s boxer brief waste band. Well, Everlane has done just that, and it just might be a new favorite for us. Simple things are harder to design – everything has to be just right. So after two years and 12 prototypes, Everlane delivers a meticulous fit in an amazing US-grown supima cotton and a soft no-branding waste band. Going a step further in keeping it minimalist, they offer classic colors and no patterns. Not sure? The Uniform 365-day guarantee makes it easy.

Calvin Klein Boxer Briefs

Most Iconic: Calvin Klein Modern Cotton Stretch Boxer Brief

In the 90’s, Calvin Klein had us all thinking that wearing Calvin Kleins was the only thing to do. Everything else would work out. And it wasn’t just Kate Moss and Mark Wahlberg. I mean, they were the stars, but everyone in their ads just looked so effortlessly cool, and, man, were those ads hot. Many were deemed too hot for TV and were outright banned. Today, if my waistband has to be branded, I’d still rather it says CK, thank you very much. (Hi, Kate.) 

The Modern Cotton Stretch is extra soft and has what the 90’s didn’t have…stretch. So these bad boys won’t ride up your legs and bunch up, and they’re much thinner. They’re super breathable, retain shape for a long time, and the iconic waistband is really comfortable. These have a contoured pouch for extra support, adding even more comfort. All good things come in threes, and we’re in luck, because that’s how these are packaged. Best of all, they’re your girl’s favorite, too.

J Crew printed boxers with astronauts in navy blue

Best Breathability: J.Crew Printed Boxers

If I had to choose one word to describe the J.Crew printed boxers, it would be “classic.” J.Crew has a reputation for preppy, no-gimmick Americana, and these boxers are no exception. Offered in a huge assortment of rich colors and patterns, these are great for summer days. The loose fit keeps things super breathable and free, and the colors and patterns are so nice these could double as a swim trunks if you were in a jam.  The organic cotton and brushed cotton waist band keeps everything soft and comfortable, and discreet branding and a fly front keep these classy. We love the Blue Anchor Ropes, the Sunset Beach, and the Boxing Crabs, but don’t take our word for it. Find your favorite.

Royal Silk Crimson Tie Dye silk boxers

Most Flirtatious: Royal Silk Crimson Tie Dye Boxers

These silk boxers will have you feeling frisky all day long. Your confidence will be at an all-time high throughout your day. These are definitely not your dad’s silk boxers. Tie dye and silk go hand in hand, and this fabric is obviously the right choice for this rich dye. The colors are super vibrant but somehow it works and doesn’t overpower the shorts. We love these and would definitely wear them on our next Tinder date. Royal Silk offers a variety of colors to choose from and they also sell a silk washing bag at a reasonable price to help you out with your silk maintenance.

Derek Rose Silk Boxers

Best Luxury Pick: Derek Rose Classic Fit Boxer Shorts

Derek Rose began making boxer shorts to use up remaining fabrics from their pyjama productions. They decided to keep the 2-button adjustable waistband on the underwear in order to maintain the same level of quality and comfort. The cut is great for those who prefer a little more room than classic boxers and a nice, relaxed fit. The silk is beautiful and has a soft satin finish. I love that these are only offered in rich Navy. For a more streamlined fit, try the “modern fit” options. These are built with a flat fell center seam with enclosed material edges for minimal skin contact and less irritation. These boxers are ridiculously comfortable and about as understated as silk boxers could ever be. I would wear these every day.

Ralph Lauren Polo Boxers

Best Cotton Boxers: Polo Classic 3-Pack

Ralph Lauren has been dressing men from head to toe for longer than most of us have been buying our own underwear, and no one does it better. When it comes to boxer shorts, Polo uses lightweight breathable cotton and puts it together in a classic silhouette, with open fly and soft elasticized waist. The classic 3-pack is a no-brainer. They offer a ton of colors and patterns at a modest price. So if you’re looking for a tried-and-true pair of boxers, these are a great choice.

Mack Weldon Airknit Boxer Briefs

Best Tech: Mack Weldon AIRKNITx Boxer Brief

Mack Weldon claims to be reinventing men’s basics, and we have to agree – the AIRKNITx Boxer Brief stands out amongst everything out there. The soft, lightweight microfiber maximizes airflow and stretches in all directions. These also feature an odor-fighting, moisture-wicking finish to keep you dry through workouts and long workdays. The fit is super comfortable. With the supportive pouch, no-roll waistband, and stay-put leg construction, it’s easily one of the most comfortable boxers out there.


As mentioned earlier, picking just one fabric is a challenge, but we love the AIRKNITx microfiber as it has all the technical properties you would want in a undershort while not looking more fashion than sporty.

Men have been trying to answer this question for years. 90% of the time, briefs will keep you more comfortable and will require less adjustments throughout the day. But on a nice summer day on the boat, reach for that boxer short. Their breathability can’t be beat.

Does this pair of boxers still make you feel a little tinge of confidence when you put them on? If the answer is no, it’s time for these to go.

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