Best Underwear Overall
Calvin Klein Men’s Cotton Classics Trunk, 5 Pack
Best Underwear Overall
Calvin Klein Men’s Cotton Classics Trunk, 5 Pack
Now 24% Off
Yes, we kicked the list off with Calvins because you’re the champ until someone knocks you out. Last time we checked, which was just now, Clavin Kleins are still the most beloved underwear out there.
Best Amazon Aware Underwear
Amazon Aware Relaxed-Fit Cotton Modal Boxer Short, 3 Pack
Best Amazon Aware Underwear
Amazon Aware Relaxed-Fit Cotton Modal Boxer Short, 3 Pack
Amazon Aware (the retailer’s in-house brand) produces stylish basics on the low. For example, these relaxed fit boxers are made from a blend of cotton and modal that is Organic Content Standard certified. Easy on your bum and the planet.
Read more: Best Menswear Brands on Amazon
Best Cooling Boxer Briefs
Saxx Underwear Co. Droptemp Boxer Brief, 3 Pack
Best Cooling Boxer Briefs
Saxx Underwear Co. Droptemp Boxer Brief, 3 Pack
If you’re looking for men’s underwear that can transition from work to the gym, Saxx has you covered (literally) with its DropTemp Cooling Boxer Briefs. Its ultra breathable modal/cotton blend especially comes clutch when that summer heat rolls in.
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Most Comfortable Underwear
Tommy John Second Skin Boxer Brief, 3 Pack
Most Comfortable Underwear
Tommy John Second Skin Boxer Brief, 3 Pack
Boxer briefs are most comfortable when you forget that you’re even wearing them. Prime example: Tommy John’s Second Skin line, which features a light blend of modal and spandex, an 8 inch inseam cuts down on friction and riding up.
Best OG Underwear Brand
Hanes ComfrotSoft Boxers, 6 Pack
Best OG Underwear Brand
Hanes ComfrotSoft Boxers, 6 Pack
A comfortable-yet-secure waistband is crucial for boxers to hold them in place. That’s especially true for Hanes, which came up with a proprietary strip that’s so flexible and cozy you forget that you’re wearing it.
Brady Brady Men’s Boxer Brief, 5 Pack
Brady Brady Men’s Boxer Brief, 5 Pack
Now 30% Off
Now that Tom Brady is retired, his new career as a budding menswear designer is already off to a great start. Case in point: his brand’s top notch boxer briefs. A very specific cotton/polyester/elastic blend is supple and soft while being just snug enough to hold everything in place.
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Jockey Classic Full Rise Brief, 3 Pack
Jockey Classic Full Rise Brief, 3 Pack
Jockey has been one of the most reliable men’s underwear brands for decades, best known for their classic full rise briefs. Never a bad choice.
Polo Classic Fit Cotton Boxer Briefs
Polo Classic Fit Cotton Boxer Briefs
There is a level of quality that we’ve all come to expect from anything adorned with that Polo pony logo. It applies just as much to underwear as it does to oxford shirts and polos. Rest assured, these Ralph Lauren boxer briefs deliver with a 100% combed cotton softness.
New Balance No Fly Boxer Brief Compression Underwear, 3-Pack
New Balance No Fly Boxer Brief Compression Underwear, 3-Pack
For those who don’t already know: spandex compression shorts are just as comfortable for all-day wear as they are for workouts. Especially when the summer heat really kicks in. New Balance makes some of the best compression boxer briefs, whether you’re going to the gym after work or not.
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Pair of Thieves Everyday Cotton Boxer Briefs, 4 pack
Pair of Thieves Everyday Cotton Boxer Briefs, 4 pack
Sometimes, you just need the comfort of good old reliable cotton. Enter Pair of Thieves, which makes some of the best in class. Better still, these skivvies come in a wide range of sizing, up to a 44-inch waist.
Bamboo Cool Boxer Briefs, 3 Pack
Bamboo Cool Boxer Briefs, 3 Pack
Bamboo Cool boxer briefs not only feel good on your family jewels, they’re also easy on the environment. Made from 65% bamboo viscose—a super renewable crop because of how fast it grows—that is light, stretchy and breathable.
Gildan Boxers Assorted Multipack, 5 Pack
Gildan Boxers Assorted Multipack, 5 Pack
Gildan has a reputation for reliable and affordable basics like tees, hoodies, and especially underwear. You can’t go wrong with a five pack of no frills, does-everything-you-need-them-to-do boxers decorated in simple patterns.
Brad Lanphear
Contributing Commerce Style Writer
Brad is a contributing style commerce editor. After a decade working for menswear brands including J.Crew and Ralph Lauren, Brad switched from selling fashion to writing about it. His words have appeared in Huckberry, Heddels, and The Manual.