I’ll give you this: the biggest strike against boxer shorts, both in that 2016 GQ screed and in the world at large, is their penchant for bunching up in your pants and ruining the silhouette of your whole fit. But the thing is, in 2023, you really, truly should not be wearing pants anywhere close to as tight as you did in 2016. We’ve been living in the Age of Big Pants for years now. Isn’t it time your underwear got a little bigger, too?
So yes, by all means, keep a few pairs of boxer briefs in your underwear drawer for the gym and nights you plan on someone else seeing you in you skivvies—they do hug the body in all the right ways. But for the rest of the time? Set your privates free. Let them lounge and hang loose and experience the world as God intended. Embrace the boxer short.
The Best Boxer Shorts Overall
Polo Ralph Lauren classic fit woven boxers (3-pack)
Ralph Lauren’s boxer shorts are just as good as his button-ups—after all, the fabrics used for both are basically the same. On top of that, we love that the front of the waistband lies flat while still allowing for plenty of elastic to conform to your size.
The Best Affordable Boxer Shorts
Uniqlo woven broadcloth boxer shorts
Though these aren’t the cheapest boxers on this list, they’re the most affordable pair you can get that still uses a 100% cotton fabric. Details include an elastic waist, button fly, and side slits for improved range of motion.
The Best Boxer Shorts Cool Enough To Wear as Regular Shorts
Anonymous Ism tie-dyed cotton boxer shorts
If you ever find yourself locked out of your apartment wearing nothing but these, there’s a good chance that your neighbors wouldn’t notice anything strange about your outfit (minus the fact that you don’t have a shirt or, uh, shoes on). These boxers are one of those rare occurrences where you might even consider wearing them out as actual shorts, though we’d recommend wearing another pair of underwear beneath—y’know, just to be safe.
The Best Upgrade Boxer Shorts
Sunspel cotton boxer shorts
Sometimes something so quotidian as an undergarment gets elevated to the point where you’d say, “Why aren’t they all like this?”. Sunspel’s been in the underwear biz for generations, so it’s safe to say they’ve gotten pretty good at it. Their high-quality boxers use 100% fine long staple cotton which has a silky smooth finish and the rear panel is cut in a way that rids itself of the annoying center seam while also forming itself gracefully around your butt.
The Best Hybrid Boxer Shorts
Calvin Klein cotton classics multipack knit boxer shorts
Just like those CK briefs you know and live, only a whole lot roomier and airier.
Most boxer shorts use woven fabric, but there are a select few that take the knitted fabric route. In this case, Calvin Klein’s jersey cotton boxer shorts take all the best parts of its best selling boxer briefs and molds it into the boxer shorts frame. That means you still get the stretchy softness of boxer briefs combined with the airy freedom of boxer shirts.
The Best Soft, Sumptuous Boxer Shorts
CDLP boxer shorts (3-pack)
CDLP’s boxers use the same silken tencel lyocell fabric that made its boxer briefs a best-seller, which is great news for any boxer shorts apologist. Not only does the fabric feel great, it’s also breathes really well and can wick moisture like Dikembe Mutumbo blocks basketballs.
Plus 11 More Boxers We Love
Hanes tagless boxers (5-pack)
At under five bucks a pop, you could spring for a few packs and pad out your underwear draw for a month.
Nordstrom Supima cotton boxers (3-pack)
Anytime you can get your body into Supima cotton, do it. Especially if it’s Supima cotton underwear The super long staple cotton is prized for both its durability and smooth hand, which means you’ll be enjoying these boxers for a long time.
Mack Weldon 18-Hour jersey knit boxer
Made from an impossibly soft blend of cotton, micro modal, and spandex, Mack Weldon’s jersey boxers feel more like a cloud than underwear.
Industry of All Nations woven boxers
Old school and au naturale, Industry of All Nations’ boxers are made entirely of undyed organic cotton and forgo the usual elastic waistband in favor of a drawstring. No cotton blends, no elastane, no harmful chemicals, just good ol’ fashioned undies.
Derek Rose “Bailey” silk-satin boxer short
One surefire way to feel like absolute royalty? Silk boxers. When the weekend comes ‘round, lounging doesn’t get much more luxurious than this.
James Perse Luxe Lotus boxer shorts
James Perse’s Luxe Lotus fabric has earned the brand leagues of devotees, who line their drawers with nothing but the brand’s tees. The fabric feels closer to satin but comes with the four-way stretch and contouring characteristics of jersey. Unobtrusive flatlock stitching and carefully-designed panels make this one of the most comfy pairs of boxer shorts out there.
Paul Smith mix up boxer short
A cheery way to brighten up your undercarriage.
Brain Dead Erratic boxer short
Some boxers are made for showing off with sagging pants and a skateboard under your feet.
Tommy Jeans X Martine Rose boxer short
Collabs know no bounds.
Calvin Klein cotton classics multipack woven boxer shorts
Classic, breathable cotton boxer shorts that will not fail you. Cop at least a week’s worth and change your life forever.
Tom Ford velvet-trimmed leopard print silk-satin boxer briefs
Leave it to Tom Ford to make a pair of boxers that are equal parts fierce
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