The Best Men’s Underwear You Can Buy in 2020

Maybe you’ve been together for a few months. Maybe it’s more like a million years. Regardless, at this point in your relationship with your man, you probably know him and his preferences better than he knows himself, which is how we’ve arrived here together, just us girls reading a men’s underwear shopping guide.

Multi-packs are definitely how it’s done in the menswear space, which makes things nice and easy, and fall is an opportune time to take inventory of what he’s got stashed in the drawer before restocking for winter and spring.

Just like with women’s bras and panties, so it goes with Bare Necessities and men’s underwear. Simply put, we carry the best options on the market—nay, in the world. Our buyers start by building a curated selection of basics for everyday wear, then add a dash of colors and patterns for interest. To cover all his bases, they round out the must haves with super-specific styles for good measure. And all of this is going on inside an elevated assortment of brands that removes the question of quality from the decision-making equation.

In other words, this should be quick and painless so you can get back to doing more interesting things (like, say, shopping for yourself).

Scroll on to find our top picks for men’s underwear across lots of key categories. By taking this one shopping to-do off his list, you’re now in charge of what you see in the morning; have fun with it.

BEST OVERALL MEN’S UNDERWEAR: Polo Ralph Lauren Classic Fit Cotton Boxers 3-Pack

Polo Ralph Lauren has always stood for timeless good taste, and these multi-packs are a case in point. If he’s a dyed-in-the-wool boxers kind of a guy, these will never let him down, what with their old-favorite-T-shirt-level of stretch-cotton softness, classic color combos and unbeatable size range. Little details like the logo waistband, button fly and embroidered emblem add a lot of polish to these non-binding, feel-good, 5-star pairs.

BEST AFFORDABLE UNDERWEAR: Calvin Klein Cotton Classics Boxer Brief 3-Pack

These buttery cotton boxer-briefs deliver that perfect fit he expects for Monday to Friday at a price—less than $15 a pair—that won’t make his eyes bug out when he invariably asks what you spent on such abject comfort. They manage to strike that just-right balance between snug and roomy, in a broad spectrum of wearable neutrals. And should he eventually break the cost of these boxer briefs down to their cost-per-wear, he will find that Mr. Klein was basically paying him to wear these into the ground.

BEST MEN’S UNDERWEAR FOR CHAFING: Saxx Quest 2.0 Performance Boxer Brief

If your mister is remotely willing to try something new, we’re willing to bet he’s going to love Saxx. With a supremely innovative inner “ballpark” sling design that increases support and reduce chafing, this brand has put the most revolutionary spin on men’s underwear in recent memory. Guys also approve of Saxx’s no-fold elastics and seamless, tagless (that is to say, irritationless) design, be it for a day at the office or hours spent in the car or gym. With the Quest 2.0 fabric in particular, the breathable, quick-dry, ultra-light waffle weave also happens to come in above-average prints and an outstanding size range.

BEST COOLING UNDERWEAR: 2(x)IST Micro Speed Dri Mesh Brief 3-Pack

A minimal (okay, barely-there) cut plus moisture-wicking mesh come together in a breath of fresh air, for a cooling effect he might want year-round down there. (This is especially key if he’s big into working out.)  Made of a very soft, stretchy fabric, these design-conscious briefs have got a built-in pouch for secure support, a tagless design and a brilliant microfiber waistband (why don’t they all do that?!) for the ultimate in no-pinch ease.

BEST BOXER BRIEF: Polo Ralph Lauren Classic Fit Cotton Boxer Brief 3-Pack  

Why pledge eternal allegiance to boxers or briefs when he can get the best of both worlds? Our overall top-rated boxer shorts (see above) also make an appearance atop our best-seller list in the form of boxer-briefs. Here, you can have your pick of more than ten different (eminently wearable) color combos. Reviewers all note that you get what you pay for with these small-to-2XL shorts—comfortable stretch cotton, with an excellent body-hugging fit, and no shirking on style, either.

BEST TRUNKS: Emporio Armani Stretch Cotton Trunks

Guys want to look and feel their most put-together in their skivvies just like we do, and these slim-fit yet extremely comfortable stretch-cotton trunks get the job done. Cut to hug his curves closely from within and without (the built-in contoured pouch feels like a godsend under work pants), they excel at keeping everything right where it belongs, in lightweight and seriously eye-catching style as only Signore Armani knows how to do.

BEST MEN’S UNDERWEAR FOR TALL GUYS: Polo Ralph Lauren Classic Big & Tall Cotton Woven Boxers 2-Pack

Crisp cotton boxers are always a do…unless they tend to run too snug on your man, thus defeating the whole free-and-easy appeal boxers hold to begin with. With sizing from 1XL up to a 4XL, these fly-front, traditional plaid styles dispense with the problem altogether for your big guy. 

While good looks are no longer an afterthought, it all still—rightly so—comes down to comfort for the gents. That’s why finding the best men’s underwear across all of these different categories is so important. Once you know the best bets across the wide universe of men’s underwear styles, you can help him find the right fit that will start his days on the right foot, and that’s a win for everyone.

The following two tabs change content below.

Brooke Glassberg

Brooke is the editor of this here blog. In a previous life, she was an editor at Good Housekeeping and O, The Oprah Magazine. Brooke has written for Glamour, Travel+Leisure, New York Magazine and more. She’s into concerts, travel and her exceptionally adorable daughter and husband.

Brooke Glassberg