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Guys, It's Time to Upgrade Your Underwear

Graphic: Chelsea Stone
Style GirlfriendStyle Girlfriend is the go-to destination for guys seeking not just fashion advice, but lifestyle tips, tricks, and shortcuts - all from a friendly, female editorial team’s perspective. Each week, Team SG will round up the clothes, grooming products and more men need to live their most stylish lives.

If you’ve been thinking lately about upgrading the contents of your underwear drawer—or maybe more importantly, if you haven’t been thinking about it—let me lay down some knowledge for you guys to noodle on.

Here’s three things to keep in mind about your underwear:

  1. Men’s underwear has made a lot of advances in recent years! Think: more comfortable stitch placement. Think: no-roll waistbands. Think: pouch innovation. Meaning? There’s never been a better time to trade up.
  2. With innovation comes a price tag reflecting all that R&D. So when it comes to underwear upgrades, be prepared to spend slightly more than what you’re used to. Especially if “what you’re used to” is whichever 3-pack is cheapest at T.J. Maxx. Do you know how much women’s bras costs? Good bras? Like, upwards of $50. So don’t come crying to me when a few styles on this list are more than you paid for the entire contents of your current underwear drawer.
  3. In a highly scientific office poll, I confirmed that 100% of female respondents prefer boxer briefs over any other kind of underwear when looking at men in their underwear.

Below, the best men’s underwear to upgrade to today:

Rhone 5” Athletic Boxer Brief, $28

Rhone 5” Athletic Boxer Brief, $28
Graphic: Chelsea Stone

The material of these ultra-soft Pima cotton boxer briefs feels so lightweight, you might forget you have them on. If sudden thoughts of, “Did I go commando today?” don’t bother you, then premium DTC activewear insurgent Rhone might have made the perfect foundation garments for you.

Pair of Thieves Cool Breeze Boxer Brief, $25

Pair of Thieves Cool Breeze Boxer Brief, $25
Graphic: Chelsea Stone

True story, I went on a few dates with a guy who worked here, and he was VERY proud of the brand’s “No Swass” guarantee. What’s “swass” you may ask, like I foolishly did at a cute little cocktail bar downtown? Turns out, it stands for “swamp ass,” a phrase he repeated to me multiple times until I asked him to stop.

Swass-branding notwithstanding, Pair of Thieves does make a very stylish, very affordable pair of boxer briefs, and the fabric is indeed moisture-wicking and breathable. Let my dating-gleaned underwear intel be your gain.

Icebreaker Merino Men’s Anatomica Boxers, $30

When I first heard about Icebreaker’s merino wool underwear, I thought, “No way.” I mean, at least with wool sweaters, you can wear a long-sleeve shirt underneath if it gets itchy, right?

Prepare to be pleasantly surprised, then, as Icebreaker’s underthings feel super comfortable, thanks to nylon fibers wrapped in merino wool that regulate your body temperature naturally. Merino wool is also moisture-wicking and odor resistant. Weirdly perfect for underwear.

Uniqlo Airism Boxer Briefs, $10

Uniqlo Airism Boxer Briefs, $10
Graphic: Chelsea Stone

As a woman who lived through the low-rise jeans trend, I do not understand why any guy would want low-rise underwear. Which is why I’m sure it’s not just me excited by these “high-rise” Uniqlo boxer briefs. That’s where they should be sitting! The style also boasts anti-microbial, anti-odor, and deodorizing underwear technology (which yes, is a thing). Oh, and the stretch material has a smooth, comfortable feel that’ll make you want to buy the style in bulk.

Tommy John Second Skin Trunks, $96 for a 3-pack

Tommy John Second Skin Trunks, $96 for a 3-pack
Graphic: Chelsea Stone

A not-at-all depressing part of writing about menswear when you don’t have a boyfriend is receiving product for review and having no one in your immediate vicinity to give said-product to.

Which is how I came to gift several pairs of Tommy John second skin trunks to my best friend’s husband, and why he still tells me today how much he loves the quick draw fly—a horizontal opening that allows the wearer “easy access when you need it most.”

He also regularly sends pictures of his coffee mug while in the bathroom to both his wife and me in a shared group text that’s an inside joke I won’t even begin to get into here and has no place in polite society. Neither here nor there, but y’know, we have fun.

Everlane Boxer Brief, 2 for $28

Everlane Boxer Brief, 2 for $28
Graphic: Chelsea Stone

Made with a close fit through the leg and waist, and a soft, roll-resistant and logo-free waistband band, Everlane’s boxer briefs are a lot like the rest of the brand’s offerings—simple, no-frills yet stylish.

Constructed of domestically-grown Supima cotton (which is both softer and twice as strong as normal cotton) and just a hint of elastic, they might not last as long as some of the other styles on this list, but when you have to restock, the price tag won’t make you wince.

Mack Weldon AIRKNITx Boxer Brief, $28

Mack Weldon AIRKNITx Boxer Brief, $28
Graphic: Chelsea Stone

Possibly the best-looking pair on this list, Mack Weldon’s AIRKNITx boxer briefs are soft, lightweight, and might just make you want to walk around in your underwear all day. Microfiber maximizes airflow and stretches in every direction, while moisture-wicking and odor-fighting components will keep you dry and fresh all day.


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About the author

Megan Collins

Megan Collins started Style Girlfriend to help guys look and feel their best. Today, she and her team share tips, tricks, and shortcuts to a closet that inspires confidence.