Men’s Comfortable Underwear: 10 Best Styles

mens comfortable underwear


It’s time to get a little personal. And holy cow: for being such a personal subject, there’s a lot of information out there about men’s undies. It seems like everyone’s got something to say about it/them. I know this because I have spent many hours of research to learn about underwear for men. I feel like I’m doing you a public/pubic service by sorting through all of it and narrowing this list down to Men’s Comfortable Underwear: 10 Best Styles.

UPDATE – The list has been updated as of May 15, 2018. Besides price updates on all the styles, we’ve removed a brand and replaced it them with the David Archy double pouch trunks, which are extremely popular with customers.

Men’s Underwear: Which Type?

From the many (and, again, many) comments about underwear on the Internet, it seems that tighty whiteys are a no-no. I’ll generalize and say that, generally, it appears that the observers of underwear clad dudes don’t like tighty whiteys on the dudes they are observing. I only bring the observers into the mix because the look is part of the underwear equation. Mostly, though, our list is focusing on comfort, no matter which type of unders you wear.

That said, there seems to be some recent empirical evidence that boxer briefs are the overall preferred-by-women underwear for guys. A survey by GQ Magazine showed that 64.5 percent of women preferred boxer briefs on guys, 19 percent like the boxers, 11.5% like trunks and five percent like the briefs. (We realize that it is not only women who observe men in undies. It was GQ’s survey.)

Best Men’s Underwear: The Categories

While I tend to call the entire category “undies,” there are specific types of undies.

Briefs – This is the basic style. Provides full frontal and backal (okay, back) coverage. The elastic leg goes mid/upper thigh. If they were white, they’d be tighty whiteys. You know what I’m talking about.
Boxers – Again, you know what I’m talking about. They’re, basically, mid-thigh shorts in thinner material than shorts and, usually, they’ve got a fly.
Boxer Briefs – A hybrid between the two. Toward the top, they’re briefs. Toward the bottom, they’re boxers, but the leg is usually elastic around the thigh.
Trunks – These are simply shorter boxer briefs.
Bikini Briefs – Think “Speedos.”
Jockstraps – Initially a protective undergarment for use during athletics, these are a style of underwear worn by some.
G-Strings – More like a jockstrap in front, with a “string” of fabric going up the middle of the backside to reunite with the (usually very small) waistband.

What Is “Comfortable” Underwear?

Whether or not men have been asking this question, we’re quite certain that they’ve consciously or unconsciously tapped into the question and, more importantly, the search for the answer since Cro-Magnon was lumbering around commando style in his fur toga. In this case, we must admit that the answer to the question is elusive. It’s a subjective issue. Take me, for instance. Back in the day, I was all about going commando. I truly thought that wearing underwear was overdoing it. Why did I need another layer of clothing? A few years later, I came to the conclusion that boxers were cool, so I started wearing boxers. (Why did I think boxers were cool? Perhaps because they were what men wore, as opposed to the tighties I’d worn as a boy. I wanted to be manly.) And, later still, I decided that boxer briefs were the thing because I liked the snugger fit. It felt right…it feels right to me. But, overall, there are some obvious reasons you’re here checking out the list.

* You want to know the best men’s underwear for hot weather
* You want to look for men’s boxer briefs — or any other style — that won’t ride up (i.e., are the most comfortable men’s underwear you can get)
* You want to get the best men’s underwear possible

Whatever it is, we’ve got you covered (and so stylishly).

Men’s Underwear: The Movie

If you need a bit more “Men’s Underwear 101,” take a look at this video from the good people at The Underwear Expert. They strip it down (literally, I guess) to the basics.

What About Silk Underwear for Men?

When you think about the other factors that go into a comfy pair of underwear, the fabric is an obvious element to consider. So what could be more comfortable than silk? Well, fur-lined, maybe? Maybe not. Suffice to say we’re not delving into the silk (or fur-lined, if there is such a thing) here. That’s for a different list, to wit: the Top 10 Best Men’s Silk Underwear on Amazon. We won’t offer any spoilers for that list, but the fact is that there aren’t a lot of makers of silk undies out there.

Men’s Underwear: How Many Per Package?

One last thing: as you consider the type and style of undies, pay particular attention to the number offered per package. We’ve pointed out how many each package includes (and we realize that we’ve got a double entendre going with this). And while they are numbered one through 10, we’re not really ranking them. They appear in random order.

Men’s Underwear: Men’s Funderwear

Of course, we could have included the “mankini,” which gained brief (thankfully, and pun intended) notoriety when the actor Sasha Baron Cohen paraded around in a mankini in the movie Borat. But we’re not going to suggest mankinis on this list.* In fact, we’re focusing primarily on boxer briefs, trunks and briefs. We think the remaining categories are perhaps for a different list/different purpose/different day.

Now onward toward getting the best men’s underwear you ever had after you take a look at our list of Men’s Comfortable Underwear: 10 Best Styles.

1. Calvin Klein 2-Pack Men’s Underwear Modern Cotton Stretch Trunks

calvin klein 2-pack mens underwear modern cotton stretch trunks

Calvin Klein

These trunks were named recently by GQ as the best pair of underwear you can get. Like most reviews, theirs was, largely, subjective. They gave four main reasons for their rating: the fabric, the comfort, the fact that these stay put and that they “flatter every body type.” It’s not really a surprise to see Calvin Klein joints make such a strong showing, given the fact that Calvin practically invented the comfy undie industry back in the day. These are not boxer briefs; rather, they’re trunks, which is just like a men’s boxer brief only with much shorter inseams. Two things to take careful note of: they come in a two pack (works out to around 30 bucks for the size I wear – large); and, secondly, they don’t have a fly. They come in 12 different colors.

Price: $11.01 and up (depending on size selected)

Buy the Calvin Klein 2 Pak Stretch Trunks here.

2. Tani USA SilkCut Hip Brief

tani silk cut hip briefs

Tani USA

For those of you who want a bit less fabric, the bikini brief could be your ride (Tani USA simply calls their model a “hip brief,” not a bikini brief). These SilkCuts are, according to the company, created by using “Europe’s most sophisticated fine-gauge knitting machines to produce this extraordinary fabric.” Despite the name, it’s not silk, but the company says it’s softer and more durable than silk and a naturally wicking fabric. They are made using a proprietary fabric called Micro Modal Air (94%) and elastane (6%). They don’t have a fly but, unique among the rest of the models in the list, they’re biodegradable. (That doesn’t mean you can fling them out the car window and tell the officer, “But they’re biodegradable.”) These are offered in three different colors. One per package.

Price: $30 and up (depending on size/color selected)

Buy the Tani USA SilkCut Hip Brief here.

3. Saxx Underwear Men’s Vibe Modern Fit Boxer Briefs

saxx underwear mens vibe modern fit boxer briefs


Saxx just calls them “modern fit boxers,” but they are, in fact, boxer briefs. They’re also unique among the other entries on the list because Saxx features a pouch in the crotch. That is, they’re built so you can put your “family” in its own little section of the undies. According to the company’s website, the founder wanted to create a completely chafe-free environment. I’ve tried them and I do like the way they “organize” things down there. There are more than 1,200 reviews on Amazon, with almost a 4.4 out of 5-star rating average. They’re 95% Viscose, 5% Spandex. While this model is without a fly, Saxx does offer this style, which does have a fly. One per package. These come in about 10 jillion different colors. We’d be more specific but our fingers died while we were scrolling the mouse through all the options.

Price: $12.99 and up (depending on size/color selected)

Buy the Saxx Vibe Boxer Briefs here.

4. Cariloha Bamboo Boxer Briefs with Fly

cariloha bamboo boxer briefs with fly


By including this model of men’s boxer briefs, we initially thought we simply wanted to provide a unique option for shoppers: these are made out of bamboo. But reading the reviews — more than 700 reviews with a 4.6 out of 5-star rating average — it’s clear that Cariloha has a legion of fans who say these guys are all about comfort. They are classic boxer briefs and they do include a fly. Depending on your size, they’re available in nine different colors, including a white pair with no fly. The company says they’re odor resistant and moisture wicking. At the time of this writing, they were on a buy-3-get-1-free promotion. One per package.

Price: $22

Buy the Cariloha Bamboo Boxer Briefs here.

5. Under Armour Original Series Boxerjock 2-Pack

under armour original series boxerjock 2-pack

Under Armour

As you would probably expect from Under Armour, this model is pretty technical. That’s not to say that it’s fully an athlete-only joint, because plenty of the reviews mention the fact that they’re just great for comfort. This model of men’s boxer briefs (yes, they call them “Boxerjocks”) fits “next-to-skin without the squeeze,” according to the company. One reviewer did say they stay dry and work very well for wearing in the southern part of the country, where it’s hot and humid. UA credits the dryness to its “HeatGear” fabric (90% poly, 10% elastane) and the “moisture transport system.” These are extraordinarily popular with customers: more than 490 reviews with a 4.5 out of 5-star rating average. If you’re a mesh type of guy, check out this style, which UA says is “unrivaled” in breathability. The Boxerjocks also come with an “anti-odor technology” for those of you who may need to address an issue like that. BTW, a ton of color options here: 27. Two per package.

Price: $26.25 and up (depending on size/color selected)

Buy the Under Armour O Series Boxerjock here.

6. Kayizu Cotton Stretch Boxer Briefs 6-Pack

kayizu cotton stretch boxer briefs 6-pack


The Kayizu Cotton Stretch Boxer Briefs are a classic boxer brief with 95% cotton and 5% Spandex. Out of the 60 reviews — with a 4 out of 5-star rating average — there are lots of mentions about the feel and fit, particularly focusing on the fact that the legs don’t ride up. Two key points to make on this one: it’s not a specialized material, it’s good old cotton (with that five percent Spandex for stretchability). That said, reviewers made plenty of mentions about these keeping dry. Secondly, the six pack makes these very affordable. My large size comes in at $23.68, which works out to about four bucks per undie. They’re also available in “infinity blue” as a one pack, which is the lowest price point. And for those of you who drink a lot of beer (or water, or any other beverage), they do have a fly. The sixer is comprised of blacks, grays and blue.

Price: $21.99

Buy the Kayizu Cotton Stretch Boxer Briefs here.

7. Baleaf 9” Sport 2-Pack Boxer Briefs Performance Underwear

baleaf sport 2-pack boxer briefs performance underwear


We’re throwing these into the mix because there are guys out there who like that more athletic look and feel. And with the nine inch inseam, these certainly hit both marks. They look like cycling shorts, which isn’t a stretch given that Baleaf is a company that makes gear for cyclists, surfers, runners, etc. Many of the reviews mention that these stay put and don’t ride up the leg. (Of the more than 110 reviews, these average a 4.5 out of 5-star rating average.) If you’re interested in something with a more traditional leg, take a look at the six inch inseams here. The wicking material of this model is 90% poly, 10% elastane. The mesh pouch in the crotch area does include a fly. Two per package.

Price: $17.99-$18.99 (depending on size/color selected)

Buy the Baleaf 9” Sport Boxer Briefs here.

8. ExOfficio Give-N-Go Sport Mesh Boxer Briefs

exofficio sport mesh boxer briefs


While most of the models in this list are made of techy materials that dry fast and wick the moisture away from the skin, these ExOfficios leave no doubt, given that they’re a mesh boxer brief (they’re 92% nylon, 8% Lycra). As we’ve mentioned, a big advantage of these types of materials is that they’re great for travelers who want to cut down on over stuffing the carry-on. ExOfficio, with a wink, says about this model: “Just one pair (ok, maybe two) can last a seven day journey through 500 miles.” We say, make sure you find a sink to wash the one or two pairs along the way. V-popular with customers, averaging a 4.3 out of 5-stars. One per package. Plenty of color options available: 14.

Price: $14.97 and up (depending on size/color selected)

Buy the ExOfficio Give-N-Go Sport Mesh Boxer Briefs here.

9. 2(X)IST Essential Cotton 3-Pack Men’s Contour Pouch Briefs

2(x)ist essential cotton 3-pack mens contour pouch briefs


Possibly one of the most popular models in the list. I do have some trunks from 2(X)IST and I can verify that they are very nice. (They were provided to me by 2(X)IST.) These men’s underwear are contour pouch briefs and they’re 100 percent cotton. There are more than 600 reviews, with a 4.4 out of 5-star rating average. Says one reviewer: “I gave it a try and I love them. I didn’t want to comment though until I washed them to see how much shrinkage there would be, but they passed the test, they still fit great. Awesome everyday, comfortable underwear. Four thumbs up!” Always appreciate the real reviews, especially from a guy who’s got the balls to talk about shrinkage in this context. Three per package and a variety of colors to choose from: 19.

Price: $18.37 and up (depending on size/color selected)

Buy the 2(X)IST Essential Cotton 3 Pack here.

10. David Archy Men’s 4-Pack Separate Pouches Trunks

david archy mens 4-pack separate pouches trunks

David Archy

We’re not sure whether these are technologically advanced or just dang logical. These men’s briefs are called “separate pouches fly trunks” because they have separate pouches. That is, one for the twig, one for the berries. If you need more explanation, find an urban dictionary. Suffice to say that “the boys” are in their own pouch and the taller member of the crew is placed into his own hole and, thereby, into his own separate pouch. David Archy calls these “newly developed magic underwear.” They must have something going for them because they get crazy-good reviews: out of more than 2,600 reviews, they come in with a 4.3 out of 5-star rating average. The material is Lenzing micro modal and Spandex and they have a breathable panel that allows air flow. They do have a fly. The David Archys come in a four pack. Available in 11 different colors.

Price: $29.99 and up (depending on size/color selected)

Buy the David Archy Men’s Separate Pouches Trunks here.

* (Okay, if you really have your heart set on a mankini, here’s a “colorful” version on Amazon.)

Heavy, Inc. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by linking to Amazon. Our product recommendations are guided solely by our editors. We have no relationship with manufacturers.

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