Updated December 25, 2019 by Gia Vescovi-Chiordi

The 10 Best Mens Underwear

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Best High-End
Best Mid-Range
Best Inexpensive

This wiki has been updated 30 times since it was first published in March of 2015. Gentlemen, you may think that because they are rarely seen, your "smalls" are the least important item in your wardrobe. Nothing could be further from the truth. Wearing the wrong type of men's underwear can lead to itching and irritation, overheating, and discomfort all day long. Find a pair from our selection that not only feel good, but look great, too, for those intimate occasions. When users buy our independently chosen editorial recommendations, we may earn commissions to help fund the Wiki. Skip to the best mens underwear on Amazon.

10. Fruit of the Loom Assorted

9. Eyushijia Bamboo Fiber

8. Jockey Classic 9950

7. David Archy Breathable

6. Calvin Klein Cotton Classics

5. Jinshi Soft

4. Hanes Exposed

3. Under Armour Boxerjock

2. Chill Boys Quick-Dry

1. Saxx Underwear Co. Kinetic

Special Honors

Mack Weldon 18-Hour Jersey Offered in dozens of colors and patterns to suit your aesthetic tastes, the 18-Hour Jersey Boxer Brief by Mack Weldon use a proprietary blend of cotton, smooth modal, and stretch Lycra that rests for 18 hours before it's cut for a softer feel and consistent fit. Each pair is outfitted with a no-roll waistband, mesh cooling zones, and stay-put legs. mackweldon.com

Derek Rose Modern Fit Brindisi 37 Men who prefer boxer shorts with a slimmer fit than most others will appreciate this silhouette by Derek Rose. The Brindisi 37 feature an understated geometric pattern that's inspired by the Botanic Garden of Santa Barbara, California, and is digitally printed in Italy on fine silk. Each pair is hand-cut and sewn, with a slim fit that's specially designed to touch the skin as little as possible. They also boast a self-seeking magnetic fly for easy opening and hassle-free closure. derekrose.com

Zimmerli 286 Sea Island Those looking for a luxurious pair of underwear should consider the handmade 286 Sea Island fashion pant from Swiss company Zimmerli. They're crafted using extremely rare Sea Island cotton, which is handpicked in Barbados, has a natural silky shine, and is nearly as soft as cashmere and silk. They boast a discreet waistband and seams that won't show through tailored pants and fitted jeans. zimmerli.com

Editor's Notes

December 21, 2019:

To cater to men of all shapes and sizes, we did our best to provide a diverse assortment of options and prioritized designs that are thoughtful and smart. We looked for features like anti-roll waistbands, flat-out seams, tagless interiors, no-wedgie designs, and no-gap flies (with and without buttons). We also wanted fabrics that breathe well, move easily without bunching or riding up, and wash well without losing its shape. We ensured our selection had briefs, boxer briefs, and classic boxers, with sizes that go up to double and triple XL.

We've rounded up underwear ideal for daily wear, even with skinny jeans, and sleek designs that could easily be worn beneath slacks or tailored trousers without showing bulky seams. Every item on our list is designed to keep you cool and be lightweight, yet still supportive, but if you need something hardier for a colder climate, we'd suggest looking into long underwear styles.

Today we said goodbye to the Puma Tech due to repeated complaints about the seams splitting very quickly after purchase. We're recommending the Under Armour Boxerjock in their stead. This option is very similar in design, except is more resilient, has four-way stretch, uses patented "HeatGear" fabric to keep you cool, and has anti-odor technology.

We also let the Jockey Microfiber Performance go due to deliverability issues, and added the much-loved brand Saxx in its stead. The Saxx Underwear Co. Kinetic feature an incredibly thoughtful construction and are meant to feel like they're barely there thanks to their flat-out seams and patented pouch. The idea is to lessen skin-against-skin contact to prevent irritation, which makes them a great choice for long-distance runners and other athletes who run the risk of chafing while they train.

The Closest Thing To Your Body

We’ve all gone through those brief phases, perhaps lasting only a day, perhaps extending into the years, when we disdain to wear underwear.

We’ve all gone through those brief phases, perhaps lasting only a day, perhaps extending into the years, when we disdain to wear underwear. Going commando, they call it. It’s a thrilling feeling if for no other reason than that it’s a deviation from the quotidian, and a deviation centralized in an area known for its regularity.

It never seems to last though, this underwear-free phase. Sometimes the problem is a physical one, the irrepressible chafing of a new pair of jeans against a particularly sensitive organ, for example. The change could also come from your climate. After all, one of the primary functions of a pair of underwear is the absorption of unsightly perspiration, and nothing says, “I’m single; come and get me!” like a suspiciously soaked set of trousers.

So we revert, if we ever really left, to wearing underpants. And at the end of the day, this is a good thing.

Not everybody is going to see your underwear. Depending on how long a given pair lasts, and how many people get to know you on an intimate level in that amount of time, you might have pairs that meet only a few sets of eyes other than your own. It's preferable to have a pair of underwear eroding over time in place of your pants or your flesh. They serve as a protective layer between your skin and less forgiving fabrics.

Above all else, though, a good pair of underwear will give you the one thing every man can use more of: confidence. The comfortable hug of a brief or boxer brief on a cool Fall's day, or the loose airiness of a freshly washed pair of boxers on a hot Summer night–these are the things that give us an extra little pep in our step, and that gleam in our eye that is utterly irresistible to whomever we might fancy.

Boxer, Briefs, Or A Little Bit Of Both?

I've owned some unsightly underwear in my day. It hasn't been anything as egregious as those oversized whities to which I cannot in good conscience attach the modifier 'tighty.' They're too loose-fitting, baggy even, to go by that name. My underwear faux pas were more honest and well-meaning: the South Park-themed boxers, the underwear model briefs (which, with my body, I had no business wearing), etc.

The cut is close to your body, and the fabric is delicate and light, like a breeze unto itself.

Fortunately for you, we've only selected underwear for our list that would get you past even the most stringent checkpoints posted by the fashion police. From here, you'll have to base your selection on personal taste. Just remember that you aren't only allowed to buy one of the suggested sets on our list. You can collect them all.

If you are going to get choosy, I'd like to put you on the red carpet and ask you that uncomfortable celebrity question: Boxers or briefs? If you didn't answer, "It depends," then we have some work to do.

I'm not particularly concerned with which style of underwear you find the most comfortable. Underwear this nice is its own kind of fashion accessory, and fashion is not about comfort. You need to own different cuts of underwear for different pants and different climates, lest you ruin the lie of a good, expensive suit.

Imagine you've got yourself invited to a fancy event, and you go out and spend, say, $2,500 on a nice suit. The cut is close to your body, and the fabric is delicate and light, like a breeze unto itself. But you're a consummate boxers guy; it's all you have in your closet. And they all hang loose, just the way you like them.

The only problem is that there's nothing about this suit that hangs loose, so you go and stuff your oversized boxers into this perfectly tailored pair of pants and spend the night being victimized by private wagers regarding your continence.

The moral of the story is a simple one: invest in different underwear styles, and you'll never go from being the bell of the ball to the butt of its most brutal jokes.

Beware Your Shame

It's not an easy thing to pinpoint the moment at which mankind looked down at his genitals and thought better about their flying freely. Perhaps it was a protective measure, intended to keep a rather important area guarded against thorns in areas of prickly foliage. It is also possible, though far less likely according to evolutionary psychologists, that men developed something akin to shame regarding their junk in primitive societies.

It's not an easy thing to pinpoint the moment at which mankind looked down at his genitals and thought better about their flying freely.

What we do know at this point is that archeologists have dated the oldest known example of a leather loincloth to approximately 5,000 B.C.E. Of course, there are also artistic representations of clothing in ancient Egyptian artworks dating back to approximately 3,000 B.C.E., but it's hard to know whether or not the people depicted are wearing anything underneath their shifts.

The evolution of underpants remained stagnant (with the notable and ever-exciting exception of the codpiece) until the spinning jenny and the cotton gin made the mass production of underwear a viable economic enterprise in the later 1800s. From that point onward, underwear manufacture took on the terms and shapes we still use today, with styles growing tighter and tighter, even in men's underwear, as we've moved into the 21st century.

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Gia Vescovi-Chiordi
Last updated on December 25, 2019 by Gia Vescovi-Chiordi

Born in Arizona, Gia is a writer and autodidact who fled the heat of the desert for California, where she enjoys drinking beer, overanalyzing the minutiae of life, and channeling Rick Steves. After arriving in Los Angeles a decade ago, she quickly nabbed a copywriting job at a major clothing company and derived years of editing and proofreading experience from her tenure there, all while sharpening her skills further with myriad freelance projects. In her spare time, she teaches herself French and Italian, has earned an ESL teaching certificate, traveled extensively throughout Europe and the United States, and unashamedly devours television shows and books. The result of these pursuits is expertise in fashion, travel, beauty, literature, textbooks, and pop culture, in addition to whatever obsession consumes her next.


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