11 Best Men’s Underwear: The Most Comfortable

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’s 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 are 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 are available in a number of different sizes, colors and underwear per pack.

Side note: I actually wear these and swear by them. They are comfortable, the sizes are perfect and the colors are spectacular.

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.

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. Saxx provided me with a sample and I’ve tried them and I do like the way they “organize” things down there. (In fact, I don’t think I’m ever going back to non-pouch undies.)

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. Definitely check out as many options until you find the right color or colors for your style. 

By including this model of men’s boxer briefs, I initially thought I was just providing a unique option for shoppers: these are made out of bamboo. There are a ton of reviews on these undies so 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. You should definitely check them out in multiple colors, mix things up a bit and buy some new shades, you’ll thank me later. One per package.

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 (UA calls 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 when it’s hot and humid. UA credits the dryness to its “HeatGear” fabric (90% poly, 10% elastane) and the “moisture transport system.”

 If you’re a mesh type of guy, check out this style, which UA says is “unrivaled” in breathability. The Boxerjocks also comes 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.

The Kayizu Cotton Stretch Boxer Briefs are a classic boxer brief with 95% cotton and 5% Spandex. In the reviews for these boxers, 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 staying dry. Secondly, the six-pack makes these very affordable. 

They’re also available in “infinity blue” as a six-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 six-pack (of underwear) is comprised of blacks, grays and blue.

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 will stay put and don’t ride up the leg. If you’re interested in something with a baggier fit, take a look at the workout shorts.  They aren’t traditional boxer briefs or even underwear, but they make for great shorts to sleep in or run/workout in. 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. You can also find them in a 3″ model which is more of a traditional boxer brief, check those out here. 

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 overstuffing 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. Tons of great reviews and extremely popular among the workout community Plenty of color options available: 14.

Possibly one of the most popular models in the list. These men’s underwear are contour pouch briefs and they’re 100 percent cotton. 

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: 20.

I do have some contour pouch briefs from 2(X)IST (provided to me by 2(X)IST) and I can verify that they are very nice, especially with the pouch. Don’t knock it until you’ve tried it.

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.” The material is Lenzing micro modal and Spandex and they have a breathable panel that allows airflow. They do have a fly. The David Archys come in a four-pack. Available in over 7 different colors.

I’m including another style from 2(X)IST because I have a personal relationship with this style. (The company sent me several pairs, and this style is one of them…and it’s my favorite style they make.) As I mentioned about the SAXX’s (item #3), a pouch is great and these No-Shows have a pouch.

Whereas the SAXX has a funky built-in pouch that’s sewn into the undies, the pouch on the 2(X)IST No-Shows is simply an extra portion of fabric that they call a “contour” pouch. (For those of you who speak in fabric-talk, it’s kinda like having an extruded gusset.) Either way, pouches are the way to go. Very comfortable, and they really make a difference.

These are 95 percent cotton and five percent spandex, so they’re nice and snug. We’re showing them in the cheetah print, but they’re available in a ton of different prints/colors (18 at last count, although color availability periodically changes).

One per package.