Let's Go Shopping

The Best Men’s Underwear, Chosen by Women

Don't get 'em in a bunch before reading this

By Style Girlfriend | Last Updated: May 27 2020

By now, you know the importance of pulling together a wardrobe full of foundation pieces to keep you ready for any and all occasions. So why do so few guys extend this investment-minded strategy to their…well, foundation

Women have understood this “look good (even when no one can see it), feel good” factor a long time. And it’s the perfect time for you guys catch up!

Below, 5 things you may not know about finding the best underwear for men:

1. Base layers affect your entire outfit

Ready to take a page out of women’s style playbooks? For everyday confidence, give more thought to your underwear first. 

“If you have the right fitting underwear, everything else fits better. Women would never wear a baggy bra or saggy underwear. Similarly, men look and feel much better when they take a 21st century approach to their base layers,”  says Tom Patterson, Founder & CEO of Tommy John. We couldn’t agree more.

As suits and pants become slimmer, take both comfort and appearance into account when choosing your underwear.

Combatting visible lines (what us ladies call VPL, or “visible panty line”) has been a long and hard-fought battle for women, but it’s relatively new territory for you fellas. Luckily, plenty of brands have made improvements to both material and cut that will change how you feel and look in your clothes.

But this isn’t just a ploy on the part of marketers to get you to buy more expensive undergarments. 

Switching from the “Save” to the “(mildly) Splurge” category can be worth the increase in your wardrobe budget. According to Patterson, “Underwear is often the last upgrade in a guys closet or life,” which is crazy, considering underwear fits, fabrics, and functionality have changed more in the last two years than the last 25.

2. Not all underwear is created equal

“Guys are realizing that comfortable, high-quality underwear options do exist.” notes Tani USA president Adam Dinkes.

That’s right, guys; a 5-pack of boxers need not be your only source of underthangs. Look to big brands innovating their lines as well as online-only options emerging on “I made it ‘cuz I needed it” platforms like Kickstarter.

What kinds of improvements?

Think: more comfortable stitch placement and waist band width. To find the style that’s right for you, Dinkes suggests, “Buy two or three different pairs to see how they feel, how they fit, and what you find most comfortable.”

Most importantly? Don’t assume the style (or even size) you’ve always worn is the most comfortable.  Try some new fabrics and some new shapes.  Odds are there’s a whole new world of comfort out there.

3. Fabric matters

Let’s do a quick rundown, shall we?

Moisture-wicking: Pulling moisture away from your body and drying considerably faster than traditional cotton is an ideal undergarment quality regardless of season, so keep an eye out for this to be a component of most new lines.

Antimicrobial: Your first line of defense against imminent sweat? The bacteria (and odor) resistant antimicrobial property of certain fabrics in a lot of garments today. Look for this on the label next time your shopping for active or everyday underwear.

Micromodal: The finest of undergarment fabrics that results in a seriously soft feel with an almost airy weight. It’ll dry quick and offer an endless stretch – making it perfect under your skinny jeans or three-piece suit.

Classic cotton: Already known for its cool, dry comfort, updated cotton fabrics now dry considerably faster for a soft feel that will remain durable.

Polyester/spandex blend: Compression shorts are known for this combination that tends to feel tighter than most fabrics, while feeling flexible enough for any workout you put them through.

…and these are just a sample of the vast fabric choices you have at your disposal. Since what you wear and where you go constantly changes, keep your underwear rotation up to par for maximum functionality.

4. Different underwear works best for different occasions

We can all agree that you wouldn’t pull on sweatpants for date night at a five-star restaurant, so why do so many guys treat their underwear as “one occasion fits all?”

If it sounds ludicrous to wear baggy boxers from your college days under a slim-fitting suit…that’s because it is.

“Loose boxer shorts are really becoming a dinosaur on the market since pants are more fitted and men want a more streamlined based layer.” says Patterson. 

There is an ever-expanding array of options available to you guys based on fit and fabric for any occasion or preference. As advocates of occasion-based undergarments, we promise there’s enough room in your dresser drawers for micromodal briefs to wear with your suit, cotton boxers to sleep in, and spandex compression shorts for your next workout.

5. Women notice!

Think about your underwear the way you think about ours! If we’re getting hot and heavy, only to reveal a sweaty sports bra and granny panties underneath our clothes, well, that’s not so attractive, right?

Another thing women don’t want to see? Public adjustments.

By better understanding how guys move, newer brands have found ways to fix your foundation’s fit. That means less rolling, bunching, and (thankfully) less adjusting.

Shop the best underwear for men, selected by the team at Style Girlfriend:

Best Overall – Tommy John Second Skin Trunk, $35

SG Says: Thanks to its weirdly innovative quick draw fly—a horizontal opening that allows the wearer “easy access when you need it most.”

Best – Low Priced ($) – Pair of Thieves Cool Breeze Boxer Briefs, $19

SG Says: You can find Pair of Thieves at Target, which is nice, as you don’t necessarily want to drop too much money on a totally refreshed underwear drawer without trying one pair first to make sure you like them.

They’re a little bigger in the leg, so if you’re walking around on skinnier stems, this style may not be for you.

Best High-end ($$$) – Mack Weldon Silver Trunk, $32

SG Says: This pair from Mack Weldon combines pima cotton with a performance fabric containing those antimicrobial and anti-odor properties we talked about earlier. They will keep you cool, dry, and fresh under your slimmest jeans and chinos.

Best of all? They somehow keep you snug while also feeling almost like…they’re not there at all? Men’s underwear magic!

Now that you’re stocked up on the best underwear for men, keep going! Get more style tips from the female POV by signing up for the weekly SG newsletter.