The Most Comfortable Men’s Underwear to Buy in 2021

most comfortable mens underwear
Image Courtesy of Everlane
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If you’re updating your underwear drawer for the first time in a long time, you might be unsure of where to start. Between direct-to-consumer brands and luxury labels, the underwear market has changed a lot, even in just the last few years. Besides a bevy of new brands, there are also new fabrics and styles you may not have even heard of. Modal and Pima are just a couple of examples of fabric options that go beyond regular cotton or polyester. And of course, the classic “boxers vs. briefs” debate doesn’t account for the fact that boxer briefs and trunks have become increasingly popular options. While there are a lot of factors to consider when shopping for men’s underwear, arguably the most important factor is comfort. That’s why we’ve rounded up some of the most comfortable men’s underwear that you can buy online. But in order to find what’s most comfortable for you, you’ll have to first weigh factors like fit, function and fabric.


The fit you choose comes down to preference and comfort. Boxers are loose, making them more breathable, while briefs, trunks and boxer briefs are more form-fitting and offer varying levels of leg coverage. Briefs offer the least leg coverage, trunks slightly more and boxer briefs provide the most leg coverage.


Arguably the biggest divide in men’s underwear isn’t boxer vs. brief, but fly vs. no fly. A fly is the traditional option, and it offers the obvious benefit of easier access. But some may prefer no fly, especially for athletic settings, because eliminating the fly cuts down on the excess fabric that can get in the way or impede breathability.


Fabric is crucial to comfort. Cotton is often the softest option, but not all cotton is created equal. You can look for Supima or Pima cotton, which is considered a premium option (extra-long fibers are used, which helps to improve softness and durability). The main problem with cotton is that, while breathable, it doesn’t do as well when wet and can take a long time to dry. Other fabrics include modal, which is considered a semi-synthetic fiber that is made from beechwood pulp. Modal is prized for softness and breathability, but it’s typically more expensive than cotton. Synthetics like polyester and nylon can be good options for athletic underwear, thanks to their moisture-wicking properties. However, synthetics aren’t as soft, sustainable or durable.

Other factors to consider include style — if anyone’s going to see your underwear, you want it to look good. Another very important consideration is the price. You wear underwear every day, so you don’t want to spend too much on something you have to wash after every use. By the same token, since you wear it every day, you want to spend enough to ensure you’re getting a quality product that will be comfortable and long-lasting — underwear is typically the first thing you put on and the last thing you take off, so all-day comfort is critical.

These are some of the best underwear options for men to buy now.


1. Uniqlo Supima Boxer Briefs


These boxer briefs from Uniqlo are made from soft Supima cotton, which is a popular option for its softness and durability. Supima cotton is also grown in the US. Sizing is limited right now for many of the solids, but these striped options are stocked in most sizes. They’re made primarily from cotton, with enough stretch to comfortably move in, and they have a comfortably stretchy waistband and a functional fly.

most comfortable mens underwear Image Courtesy of Uniqlo

Uniqlo Supima Boxer Briefs


2. Everlane The Longer Boxer Brief


Everlane’s boxer briefs come in two cuts, including this one, which it calls the longer boxer brief. It has a 4-inch inseam, providing extra leg coverage and helping to prevent the underwear from riding up. The boxer briefs are available in a range of stylish solids like navy, heather gray and burgundy. These boxer briefs are made from Supima cotton, making them very soft and comfortable.

most comfortable mens underwear Image Courtesy of Everlane

Everlane Supima Boxer Briefs


3. Calvin Klein 3-Pack Boxer Briefs


Calvin Klein is the brand that is widely credited with popularizing boxer briefs, and they still make some of the best options on the market. This three-pack includes stylish muted shades of blue and green, and the waistband features Calvin Klein’s repeating logo. They’re made from soft cotton, and they have a functional fly.

most comfortable mens underwear Image Courtesy of Nordstom

Calvin Klein 3-Pack Boxer Briefs


Gap Basic Briefs


Gap excels at basics, and that includes their simple and affordable underwear. These briefs are available in white, black and heather gray, although sizing is limited in the latter. The briefs are made from a blend of cotton and spandex, making them soft, sturdy and accommodating. They have a subtle monochromatic Gap logo that repeats across the waistband.

most comfortable mens underwear Image Courtesy of Gap

Gap Basic Briefs


Mack Weldon AIRKNITx Boxer Brief


Mack Weldon’s stylish boxer briefs are made from a fabric with a unique waffle-knit texture that’s designed to be more breathable and stretchy, keeping you comfortable and dry throughout the day. The fabric is a blend of polyamide, polyester and elastane.

most comfortable mens underwear Image Courtesy of Mack Weldon

Mack Weldon Boxer Briefs


MeUndies Trunk 3-Pack


If you’re looking for trunks, MeUndies’ stylish soft options are good ones to get. Instead of cotton, MeUndies uses modal, which is a soft, breathable fabric made from Beechwood pulp. The flatlock stitching and flyless pouch keep bulk to a minimum.

most comfortable mens underwear Image Courtesy of MeUndies

MeUndies Trunks (3-pack)



Polo Ralph Lauren 3-Pack Cotton Boxers


These cotton boxers are made from jersey-knit cotton, similar to your standard T-shirt or boxer briefs, and they have an elastic waistband with “Polo Ralph Lauren” printed in a repeating motif in contrasting white. They have a functional fly with a button to keep it closed. The boxers are long, providing extra coverage.

most comfortable mens underwear Image Courtesy of Nordstrom

Polo Ralph Lauren Boxers (3-pack)


Calvin Klein CK ONE 3 Pack Trunk


If you like the support of briefs but would prefer more coverage, these trunks from Calvin Klein are great options to get. They come in a pack of three, and they come in all-black or a black/white/gray mix. The flyless pouch is countered to provide additional support.

most comfortable mens underwear Image Courtesy of Calvin Klein

Calvin Klein 3-Pack Trunks


Adidas Men’s Boxer Brief Underwear


If you’re looking for the best performance underwear for men, we have a list for that. Otherwise, check out one of our top picks. The Adidas performance boxer brief comes in a pack of two and is made from moisture-wicking polyester and stretchy spandex, meaning it’s designed to move with you. It has a flyless design with a contoured pouch to keep you supported and comfortable.

most comfortable mens underwear Image Courtesy of Amazon

Adidas Performance Boxer Briefs


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