Nota bene: All products in this article are independently selected and vetted by InsideHook editors. If you buy something, we may earn an affiliate commission.
In the year of our lord 2023, it is inconceivable that fellas should still be wearing shitty, uncomfortable boxers under their finest chinos or 5″ inseamers. As the one article of clothing that you’re (hopefully) wearing every day, a truly excellent pair can be the difference between an uncomfortable office outing and winning the board meeting; frankly put, the best men’s underwear, typically an afterthought purchase, is perhaps the most important sartorial decision you’re asked to make.
The InsideHook Guide to Better Basics
Trust us: your socks and underwear are more important than you think.Given the gravitas of drawing up your drawers, we at InsideHook are officially here to put the kibosh on crappy boxers, briefs and trunks — after all, there are an abundance of great options in a variety of styles and fabrics for virtually every preference out there, from classic Calvin Kleins to sweat-wicking silvers by Mack Weldon. Supporting fits, sweat-wicking fabrics and a hell of a lot of cuts on the brief-to-boxer continuum are all options for any dude in the market for some new undies.
What Are the Kinds of Men’s Underwear?
There are an abundance of classifications for underwear, the most common undoutably being the cut of the garment: in laymans terms, boxers vs. briefs. We’ve broken down the four most common styles below for quick reference.
Boxer: One of the two classic underwear styles, boxers, American by birth, host a roomy, airflow-inducing fit and are typically woven from natural, soft fiber (see: cotton and its various blends) for unmatched breathability. Look for styles that hit the top of the thigh — any longer and you’ll slip into shorts material.
Boxer Brief: Increasingly popular in recent decades, the boxer brief is cut similarly to the classic boxer but features a closer cut and more structure throughout. A favorite muse for performance and sweat-wicking materials, the boxer brief is ideal for the fellow partial to stretch and support.
Trunk: A cousin of the boxer brief, trunks are made with the same tight weave and stretch materials, but opt for a shorter rise and leg than a classic boxer brief. Trunks functionally eliminate bunching, making them an ideal choice for on-the-go guys.
Briefs: Despite what the media of yore might have you believe, the brief — better known in pop culture as the infamous tighty whitey — has a bevy of merits, centered around a lockdown fit and minimal skin contact.
How We Decided:
Seeing as how we’re passionate about a comfortable boxer experience, we’ve identified, tested and reviewed some of the best men’s underwear on the market, and highlighted our favorite pairs of the best men’s underwear that really fit the bill. Below, the 16 best pairs of drawers to rock and stock for every type of dude imaginable.
The Best Men’s Underwear in 2023:
Calvin Klein 3-Pack Boxer Briefs
Style: boxer brief | material: 100% cotton | fly: functional side | sizes: S-XL | colors: 4
Why you should buy them: Like it or not, a Calvin waistband peaking out from some jeans is synonymous with sexy. The American designer’s ubiquitous briefs are not the most comfortable underwear we’ve tried (although they’ll get you through the day just fine) nor are they the most tech-heavy, but if you’re concerned with aesthetics, it is and will always be a fine option.
CDLP Boxer Brief
Style: boxer brief | material: 95% tencel lyocell/5% elastane | fly: N/A | sizes: XS-XXL | colors: 6
Why you should buy them: Swedish brand CDLP is a relative newcomer to the underwear scene, but after some serious IH testing, we can confirm that their Boxer Brief is the real deal. The lyocel-elastane blend is surprisingly soft and dodges the typical latex-y feel that performance fabrics can carry, with breathable and naturally anti-bacterial properties and added bonus.
PACT Knit Boxers
Style: boxer | material: 95% organic cotton/5% elastane | fly: button fly | sizes: S-XL | colors: 13
Why you should buy them: Refreshing airy and comfortably loose, the PACT knit boxer incorporates a soft, natural organic cotton made with no toxic chemicals and 81% less water used than conventional cotton.
Mack Weldon Silver Boxer Brief
Style: boxer brief | material: 84% supima cotton/10% ionic+ polyeste/6% lycra | fly: functional side | sizes: S-XXL | colors: 6
Why you should buy them: Silver is a known foil to sweat stink, and Mack Weldon’s Supima cotton with antimicrobial Ionic+ silver-infused briefs ensure that swamp-ass is never even a possibility.
Lululemon Always in Motion Boxer 5″ 3 Pack
Style: boxer brief | material: 91% modal /9% elastane | fly: N/A | sizes: XS-XXXL | colors: 6
Why you should buy them: As we’ve mentioned, the fast-drying, lycra-blended, anti-ball crushing A.I.M. boxer is our favorite daily boxer brief.
Uniqlo AIRism Ultra Seamless Boxer Brief
Style: boxer brief | material: 71% nylon/29% spandex | fly: N/A | sizes: S-3XL | colors: 4
Why you should buy them: The AIRism tech from Uniqlo is as innovative as we’ve seen: DRY technology and Cool Touch keep everything regulated, dry and, most importantly, cool. Our summer brief of choice, they’re the lightest non-boxer we’ve found — and with a new seamless design, they’re discreet, too.
Tom Ford Velvet-Trimmed Leopard-Print Silk-Satin Boxer Briefs
Style: boxer | material: 100% silk | fly: N/A | sizes: S-XXL | colors: 1
Why you should buy them: You don’t have to spend $300 on a pair of silk-satin leopard boxers, but you could!
Tommy John Cool Cotton Trunk
Style: trunk | material: 86% pima cotton/14% spandex | fly: horizontal | sizes: XS-4XL | colors: 14
Why you should buy them: Tommy John’s Cool Cotton moisture-wicking fabric claims to be 2-3x cooler and 4-5x faster drying than regular cotton. After weeks of testing, we can’t say we disagree.
J.Crew Printed Boxer Brief
Style: boxer brief | material: cotton/elastane | fly: functional side | sizes: XS-XXL colors: 7
Why you should buy them: With an abundance of colorful options and a cool cotton finish, you couldn’t ask for a better easy pair than these J.Crew boxers.
Jockey 3-Pack Classic 5″ Boxer Brief
Style: boxer brief | material: 100% cotton | fly: functional side | sizes: M-2XL | colors: 6
Why you should buy them: Jockey’s no-frills offering is still the best bang for your buck around.
Everlane The Uniform Supima Boxer Brief
Style: boxer brief | material: 93% supima cotton/7% elastane | fly: functional side | sizes: XS-XL | colors: 5
Why you should buy them: Part of Everlane’s Uniform Line, The Supima Boxer Brief is built to get you through daily life without any undergarment-related hassle. One of the few entrants on this list with a 365-day warranty, the Uniform Boxer is structured for the ideal balance of movement and security.
SAXX Vibes Boxer Briefs
Style: boxer brief |material: 95% viscose/5% elastane | fly: N/A | sizes: XS-XL | colors: 43
Why you should buy them: SAXX’s ergonomic fit is one of the most comfortable we’ve had the pleasure of testing. The Ballpark Pouch technology keeps everything in place, no matter what you’re up to, without any claustrophobic-inducing tightness.
Nice Laundry Slim Fit Boxer
Style: boxer | material: pima cotton/nylon | fly: button fly | sizes: S-XL | colors: 1
Why you should buy them: Nice Laundry’s Boxer is an enigma; flattering and sleek in profile, the drawers utilize high-end tailoring techniques and stretch Pima cotton for a controlled boxer that won’t look odd with slim (even skinny) pants.
Hanes Tagless Boxer Briefs 6-Pack
Style: boxer brief | material: 100% cotton | fly: functional side | sizes: S-2XL | colors: 1
Why you should buy them: Six briefs for $22 equates to less than $4 per pair — how’s that for some underwear math — with the added benefit of being tagless, making these Hanes pairs a-ok by us.
Nike Dri-FIT Ultra-Stretch Mirco Boxer Brief (3-Pack)
Style: boxer brief | material: 88% polyester/12% elastane | fly: N/A | sizes: S-XXL | colors: 1
Why you should buy them: For DRI-fit converts, Nike’s Ultra-Stretch Boxer is everything you love from your workout gear, wrapped up in a brief package.
Rhone Everyday Essentials Boxer Trunk
Style: trunk | material: comfort fabric | fly: N/A | sizes: S-XXL | colors: 3
Why you should buy them: A flexible brief and a soft cotton finish aren’t usually able to be paired this well, but Rhone’s Trunk has no limit to it’s range of motion, without any synthetic feeling.
More Like This
We've put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you'll need this season, whether it's for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.
