The Best Men’s Underwear for Reliable Comfort

Underwear might be a minuscule part of our everyday regimen and get overlooked, but if we’re being honest, it’s one of the most important parts of our getup. Not only do boxers and briefs provide adequate support for you and the boys throughout the day, but they’re also the frictionless layer between your sensitive skin and the rough fabrics that make up many of our preferred jeans/trousers. The truth is, underwear is a huge part of our ability to stay comfortable and capable throughout the day; so why not act like it? Instead of settling for a pair of underwhelming boxers, you should treat yourself. So head to the nearest clothing store, pull some off the rack, and go about your day. It’s not that easy, is it? Instead, we’ve decided to provide you guys with some quality offerings in our best men’s underwear guide.

styles of Men’s underwear

Boxers: Boxers are breezy, loose, and look more like a pair of shorts. They’re ideal for those who don’t like right-fitting garments and want some breathability.

Briefs: As far as protection goes, briefs are the most form-fitting. You’ll feel the most supported by them, but some people prefer a looser fit.

Boxer Briefs: Created by a former head of design at Calvin Klein, John Varvatos, in the ’90s, these are the perfect middle ground between the two. They offer support like briefs and length/breathability like boxers. Not too loose, and not too tight.

Trunk Briefs: These are essentially briefs with short legs. If you’re wearing tight pants, or working out, then

Long Underwear: Also referred to as “Long Johns”, these are more of a base layer for cold weather.

What to look for

Material: Unless you’re looking for a winter layer (in which case wool is appropriate), you want a majority cotton blend in your underwear. It’s durable, breathable, comfortable, and will often be blended with synthetics for some stretch and moisture-wicking properties. Modal fabric has been making the rounds in the clothing industry (you’ll see some underwear with it on our list), and it’s a sustainable cotton alternative made from beech tree pulp.

Waistband: Most waistbands will be made of elastic, so you’re looking to see if they’re covered (usually with cotton) or not, and the feel comes down to personal preference. If you really hate a waistband bunching up on you, look for underwear that has a “no-roll” waistband, or something along those lines.

Fly: Traditional vertical flys will be the most common, but some labels may switch up the design, drop it altogether, or even opt for a horizontal fly. If you want maximum support, then underwear without a fly might be for you.

Uniqlo AIRism Boxer Briefs

The Budget Pick: Uniqlo doesn’t confine itself to the creation of men’s outerwear. In fact, they make some of the most comfortable undergarments around, and the Men’s AIRism is a perfect representation of that. These lightweight offerings boast a cool touch component to keep them aerated and breezy throughout any period of wear, as well as an anti-microbial, odor-controlling architecture to help you stay fresh. Top that off with a comfortable, ultra-stretchy silhouette, and you’ve got the perfect recipe for a top-rated men’s brief.

Everlane The Supima Longer Boxer Brief

The Best Supima Underwear: Everlane’s transparent efforts towards crafting sustainable products have been noticed by the industry and fans alike, making them one of the leading green labels in the game. These boxer briefs are another entry into the sustainable lineup, and they’re made with ultra-soft Supima cotton. The waistband won’t bunch up, either, and the underwear is backed by Everlane’s 365-Day Guarantee policy, which will replace your pair if they get damaged.

Mack Weldon 18-Hour Jersey Boxer Brief

The Best Daily Drivers: Mack Weldon’s 18-Hour Jersey doesn’t have any overly complicated technologies or design additions. Instead, it relies on the tried and true fitment of the genre’s classics, catering to a more retrospective man. But that doesn’t mean that it can’t hold its own. The brief’s cotton, modal, and spandex construction helps to keep the 18-hour Jersey as soft as its competition, while a variety of attractive, eye-popping hues make way for some creative color combinations.

Nice Laundry Slim Fit Boxer

The Best Slim-Fit Boxers: Nice Luandry’s Slim-Fit Boxer is an artisanal offering that sets itself apart from the competition due to its refinement. Not only does the boxer take on a slim silhouette that gives it an aesthetically-pleasing look when worn alone, but it calls upon various high-end tailoring techniques to give it a leg up on the industry’s most notable examples, thanks, in large part, to its ultra-comfortable Pima cotton construction. If you’re looking for the perfect pair of underwear to throw on with a pair of skinny jeans, this is the right example for you.

Rhone Essentials Boxer Brief

The Best Boxer Briefs: Rhone’s Boxer Brief is an athletically-charged variant that introduces some cutting-edge features for the modern guy. They’re made with ultra-soft Pima cotton, and come complete with a bespoke “rocket pocket” to ensure frictionless wear throughout the day. But that isn’t all. If you’re looking for underwear that’s versatile, airy, and lightweight, you’ll be pleasantly surprised to find that Rhone’s unique boxer was served a heaping helping of its featherlight fabric, giving it a “zero gravity” feel that’s similar to a second skin.

Saxx Underwear Co. Vibe Super Soft

The Softest Underwear: SAXX has made a name for itself in recent years, and not because of its ridiculous name. Once you get past the amazing innuendos, marketable names, and interesting characters, the company’s underwear proves its worth, thanks to its unique design, advanced support technologies, and ultralight demeanor. Each friction-free variant calls upon anti-microbial/anti-odor implementations to keep you fresh throughout the day, while moisture-wicking fabrics, attractive designs, and a bespoke pouch provide adequate protection. But if you’re one for traditional colors or designs, don’t worry — the brand also has a plentiful selection of muted colors and common hues.

Tommy John Second Skin Brief

The Best Contouring Underwear: When the couple that started Tommy John began, they focused on making modern men’s undergarments that fit well and looked good. They’ve been successful in doing this since 2008, and the Second Skin briefs are proof they still got it. These form-fitting briefs have a horizontal fly and a contoured front pouch to keep everything in line, and the waistband is snug, but won’t roll or bunch up.

Smartwool Men’s Boxer Brief

The Best Wool Underwear: It shouldn’t come as a surprise that our best wool pick happens to be from Smartwool, because its durable gear is the default for many seeking warm Merino wool options. The label’s slim-fit boxer briefs are made with a mix of Merino wool, which is naturally odor-resistant, and recycled polyester to wick moisture. They’ve been constructed in a way that prevents chafing, and feature double front panels on the fly for extra support.

CDLP Boxer Shorts

The Best Tencel Underwear: CDLP’s Boxer Short is a testament to stylish men’s undergarments. Calling upon a trunk-like aesthetic, a loose, tailored drape, and a traced thigh, these unique boxer offerings take the traditional fitment of men’s boxers and turns it on its head, opting instead for an updated architecture that harkens back to the vintage swimmers of old. They’ve even got a signature waistband, an eco-friendly Lyocell fabric construction, and a tagless construction, ensuring that you won’t be shifting and scratching for relief throughout the day.

Sunspel Classic Boxer Shorts

The Classic Pick: Sunspel’s Classic Cotton Boxers boast enhanced coverage areas, helping to differentiate them from the more form-fitting brief, while also deviating from the “baggy” nature of other relaxed offerings. Instead, they strike the perfect balance between the two, thanks to their lightweight cotton construction, breathable openings, and stitched/paneled seams, ensuring that you’ll be able to move in any direction you want without feeling too confined.

Calvin Klein Ultra-Soft Modern Boxer Briefs

The Best Pack: Calvin Klein’s undergarments are world-renowned due to their iconic lineage, their history within the world of fashion, and their association with the industry’s most notable figures. Over the years, they’ve served as a cultural staple, adorning the midsections of celebrities and commoners, alike. The Microfiber Low-Rise is a prime example of why that is. It boasts a quick-dry design, a trunk-like silhouette, and an ultra-soft microfiber construction, keeping it in line with the brand’s alternative undergarments. Plus, they’ve even got a contoured pouch for bespoke fitment below, helping to keep you comfortable and flexible throughout the day.

The Best White Tees

When it comes to fleshing out your wardrobe, your underwear is only the first step. A simple white tee is essential to any collection, and our guide covers the best out there.