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The wrong underwear can ruin your look—and your day. Even your favorite jeans won’t feel right if fabric bunches underneath them or if your waistband is slowly strangling your torso.
And who can concentrate when you’re uncomfortable with your underwear? Solution: Upgrade to a pair from our list of the best men’s underwear.
There’s no reason to suffer anymore. Men’s underwear has come a long way since the 80-grit cotton loincloth you wore as a kid. Today’s pairs are comfy, sturdy, and stylish.
“You should own at least 10 pairs,” Matthew Marden, a New York City-based men’s stylist, tells Men’s Journal. “And definitely have a few special pairs, either for slim-fitting pants or for specific activities and sports.”
For instance, cotton briefs works well most of the time, but opt for stretchy, moisture-wicking, or anti-microbial fabrics for the gym or warmer months.
Finding the right style and fit isn’t always easy, but prioritize fit, advises Marden. “Men often buy a bigger size because they think looser is more comfortable,” he says, “but that can lead to extra fabric that can bunch under your pants.” The ideal fit is snug but comfortable, often with a little stretch.
As for style, patterns can be fun, Marden says, but they’re not for everyone. “A simple palette is the most flattering to every body type,” he says. Darker colors like navy, black, or burgundy are more forgiving because they don’t discolor easily.
Finally, know when to fold ’em: Replace damaged undies “the minute they rip,” says Marden. “They will quickly get worse with washing and wear.”
Boxers vs Briefs vs Boxer Briefs
When it comes to the underwear game, you basically have 3 options to work with. Boxers, Briefs, and Boxer Briefs. Every guy has a preference and within each preference, there are a ton of options to choose from.
Boxers are a much looser type of underwear, aimed more at comfort.
Briefs are basically the old-school kind of underwear we all grew up on. Tighty whiteys. This is for those that like a snug fit, all about that support.
Boxer briefs are the ideal middle ground. They fit snug, but not too snug. A lot of support, but plenty of room to breathe. Ideal for athletics.
What’s The Most Comfortable Underwear?
When it comes to the most comfortable underwear out there, there’s too many to count. You can go with the old school comfort of the Fruit of the Loom Woven Tartan and Plaid Boxer Multipack.
The sky’s the limit and the collection we wrangled together for you should satisfy all of your underwear needs.
Our Top 3 Picks
- Best Comfortable Basics For Everyday Wear – Mack Weldon Airknitx Boxer Brief
- Best Classic Brief – Calvin Klein Cotton Hip Briefs
- Best Boxers – Fruit of the Loom Woven Tartan and Plaid Boxer Multipack
Our roundup of the best boxers, briefs, and more can help you make sense of the sea of options. These are the pairs you need to know.
Best Classic Brief
1. Calvin Klein Cotton Hip Briefs
Are you a sucker for an iconic waistband? Us, too. Calvin Klein’s wide range of fabrics and fits makes this the go-to brand of men everywhere, many of whom opt for this cotton hip brief.
Unlike some other brands, this all-cotton brief doesn’t have that polyester sheen, and that familiar elastic at the waist is forgiving when you need a little extra room. The handy pack of four is just right to refresh your collection.Get it!
Best Affordable Basic
2. Uniqlo Supima Cotton Boxer Briefs
Sometimes, simple is all you need. Uniqlo, the go-to brand for basics, doesn’t disappoint with this folded front-fly boxer brief that’s equal parts soft, comfortable, and extremely affordable.
In fact, the price makes these an easy choice for buying in bulk when you don’t have time to shop around. Stock up in solids or prints and you’ll be set for the season.Get it!
Best Everyday Underwear
3. Mack Weldon Airknitx Boxer Brief
Whether you’re the type who starts his day with lunges or lounging, the Mack Weldon Airknitx line has an unbelievably flexible fabric that stretches to suit every activity.
The knit microfiber lets air flow while also delivering moisture and odor-fighting properties so you’ll feel fresher longer. The no-roll waistband and form-hugging legs stay put when you’re sitting still or on the run.Get it!
Best Underwear for Athletic Builds
4. Rhone Everyday Essentials Boxer Brief
These ultra-lightweight briefs feel almost like wearing nothing at all. Made from a soft blend of modal and pima cotton, the stretchy fabric won’t box in muscular legs or developed glutes. Instead, these briefs offer a range of movement with a no-roll waistband and a specially designed front pocket that keeps friction at bay.Get it!
Best Underwear for Slim Builds
5. Tommy John Second Skin Relaxed Fit Boxer
High-stretch, clingy fabric is no friend to guys with skinny legs. These modern-fit boxers offer all of the comfort of old-school versions with contemporary comfort.
Micro-modal fabric is smooth and lays flat while the thick waistband feels substantial. The horizontal fly means you’ll never fuss when you’re in a rush.Get it!
Best Travel Brief
6. Jockey Staycool+ Brief
Endless miles spent on the road or running around an airport before sitting for hours on a plane can take a toll on your fresh factor. That’s why a breathable brief is an essential travel companion. The higher leg lets you move without constant adjusting and the special stay cool cotton keeps the sweat away for a pleasant arrival.Get it!
Best Statement Underwear
7. BN3TH Classics Boxer Brief in Tie-Dye Love
Why not wear a pair to shows off your personality? Aside from being incredibly comfortable, supportive, and breathable, BN3TH underwear also comes in some eye-catching patterns as well. This Tie Die Love version is part of the brand’s “Inspiration Series,” and the bold pattern is a welcome departure from the bland neutral tones that usually flood underwear drawers.Get it!
Best Eco-Friendly Underwear
8. Nice Laundry Boxer Briefs
This innovative brand is not only eco-minded, but also design-focused. Their flexible micro-modal trunks come with a horizontal fly instead of the typical vertical flap, which streamlines your daily activities. And for an extra feel-good incentive, you’ll get a prepaid mailing label to send back old underwear and socks, which the company recycles. To date, Nice Laundry says it has recycled 462,076 items.Get it!
Best Occasion Underwear
9. Tom Ford Stretch-Cotton Boxer Briefs
Do you really want to attend a gala or walk down the aisle in underwear you bought at Target? Special occasions call for exceptional underwear, and Tom Ford makes the Maserati of briefs.
Even if you can’t afford this designer’s luxe suits or dress shirts, treat yourself to an expensive pair of his skivvies. Made in Italy from cotton with a hint of elastane, these boxer briefs exude class and sophistication, so you’ll feel like a power player just by wearing them.Get it!
Best Underwear for Traditional Types
10. Fruit of the Loom Woven Tartan and Plaid Boxer Multipack
When it comes to a traditional pair of boxers, you can’t go wrong with Fruit of The Loom. Just take a look at this multipack of flannel undies that will fit in any old school guys underwear drawer. And they’ll feel even better when you’re wearing them thanks to that 55%/45% Cotton/Polyester blend.Get it!
11. H&M Short Boxer Shorts
When your budget is tight, there’s nothing wrong with going with an ultra-economy option that also happens to be ultra-cool. These briefs offer a surprisingly good fit for the price, and the funky prints are a fun way to experiment with new looks without investing a ton of cash.Get it!
Best Underwear for Lounging
12. Mack Weldon 18-Hour Jersey Knit Boxer
We’re not advocating hanging out in your underwear as a regular habit, but with these ultra-cushy cotton jersey knit boxers, you’ll definitely be tempted to.
The covered waistband, button-fly front, and tailored fit will make you feel like you’re chilling in the most comfortable pair of shorts you’ve ever owned. Just remember to add pants when you go out in public.Get it!
Best Date Night Underwear
13. Michael Kors Performance Cotton Trunks
Subtlety can be sexy. And though you may have been expecting us to suggest a pair with a wild pattern or a gravity-defying support system, you’ll feel better in these.
When it comes to confidence, wearing a sleek and simple pair is always the best way to go. Plus, these modern trunks also come with anti-odor and wicking technology for when things start getting steamy.Get it!
Best Underwear for Creative Guys
14. Pair of Thieves Superfit Boxer Brief
If solids or stripes aren’t your idea of interesting when it comes to dress shirts, you’re probably not the guy who wears these traditional looks in underwear, either.
With everything you need in an everyday boxer—including cooling mesh, quick-drying fabric, and flat-stitched construction—these shorts offer the added benefit of eye-catching fabrics you’ll be excited to slip on every morning.Get it!
Best Boxer Brief for Playboys
15. TBô Ballsy Boxer Brief Long
This Swiss startup’s popular trunk really brings your assets to the forefront. It may look like a regular pair of boxer briefs, but the signature “man-shaped pouch” enhances the look of your manhood while also keeping it secure when you work out.
But that’s not the only focus here. The premium bamboo viscose offers support and breathability, plus temperature and odor control, for any kind of activity.Get it!
Best Underwear for Sleeping
16. Tommy Hilfiger Cotton Classics Knit Boxer
When temperatures rise and the humidity sinks in, wearing boxers to bed is a recipe for a good night’s sleep. But not just any pair will do. The waist has to be forgiving, the inseam should be low, and the fabric should be feather-soft.
You’ll feel relaxed in these jersey cotton trunks thanks to the mid-rise waist and the button fly, which reduces the risk of exposure when you toss and turn.Get it!
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