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The Best Stylish Underwear to Shop For Men in 2020

Since We Live in Our Underwear Now, Here Are the 25 Best Men's Styles to Buy Online

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If ever there was a time to invest in better underwear, it's under stay-at-home orders. From silk boxers to budget-friendly briefs that aren't short on style, POPSUGAR has got you covered with the 25 best pairs of men's underwear to buy online right now — overwear optional.

Image Source: CDLP

Ron Dorff Y-Front Briefs

Inspired by a '70s model for briefs developed by the Swedish Army, the Ron Dorff Y-Front Briefs ($36) are effortlessly cool.

Image Source: us.rondorff.com
Ron Dorff Y-Front Briefs
$36
from us.rondorff.com
Buy Now

Ron Dorff Striped Boxer Shorts

Tapered just enough, the Ron Dorff Striped Boxer Shorts ($50) speak for themselves: no logo, no frills.

Image Source: us.rondorff.com
Ron Dorff Striped Boxer Shorts
$50
from us.rondorff.com
Buy Now

Ron Dorff Home Shorts in Khaki

No better time than now for the ultrasoft home short of the early '80s to make a comeback, and the Ron Dorff Home Shorts in Khaki ($55) aim to please with 100 percent fine cotton jersey.

Image Source: us.rondorff.com
Ron Dorff Home Shorts in Khaki
$55
from us.rondorff.com
Buy Now

Skull & Bones Just the Bones Boxer Brief in Navy

Skull & Bones makes a damn good pair of upmarket, everyday underwear, and the Just the Bones Boxer Brief in Navy ($32) is no exception.

Image Source: skullandbones.com
Just the Bones Boxer Brief in Navy
$32
from skullandbones.com
Buy Now

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Skull & Bones Cotton Candy Trunk

Like its hi-res cotton-candy artwork, the Skull & Bones Cotton Candy Trunk ($28) is so suave, it bears repeating.

Image Source: skullandbones.com
Skull & Bones Cotton Candy Trunk
$28
from skullandbones.com
Buy Now

Polo Ralph Lauren Bandanna-Print Cotton Boxer

Made of 100 percent cotton, the Polo Ralph Lauren Bandanna-Print Cotton Boxer ($28) is lightweight for summer and butt-ery soft. (See what we did there?)

Image Source: ralphlauren.com
Polo Ralph Lauren Bandanna-Print Cotton Boxer
$28
from ralphlauren.com
Buy Now

Calvin Klein Cotton Classic Fit 4-Pack Hip Brief

Nothing if not classic, the Calvin Klein Cotton Classic Fit 4-Pack Hip Brief ($30 for a pack of four, originally $43) is an easy option for everyday wear and in a silhouette that's instantly recognisable.

Image Source: calvinklein.us
Calvin Klein Cotton Classic Fit 4-Pack Hip Brief
$30
from calvinklein.us
Buy Now

Diesel Fresh & Bright Brief in Blue

Sold in partnership with The Underwear Expert, the Diesel Fresh & Bright Brief in Blue ($24) lives up to its name with a thick trademark waistband and silky-smooth hand-feel.

Image Source: underwearexpert.com
Diesel Fresh & Bright Brief in Blue
$24
from underwearexpert.com
Buy Now

2(X)IST Essential Cotton Contour Pouch Brief 3-Pack

For a cut this good, there's no better value for money than a 2(X)IST Essential Cotton Contour Pouch Brief 3-Pack ($13 for a pack of three, originally $32).

Image Source: 2xist.com
2(X)IST Essential Cotton Contour Pouch Brief 3-Pack
$13
from 2xist.com
Buy Now

Charlie by Matthew Zink Bikini Brief in Python

Charlie by Matthew Zink doesn't shy away from daring designs in its classic silhouettes, and neither should you. Meet the sexy Muscle Brief in Python ($68).

Image Source: charliebymz.com
Muscle Brief in Python
$68
from charliebymz.com
Buy Now

Charlie by Matthew Zink Bikini Brief in Mahogany

We appreciate nudes done right (read: inclusively), and the Charlie Wood Collection does just that. Available in classic cuts to your taste, the low-rise Bikini Brief ($48) ranges from Mahogany (pictured) to Bamboo.

Image Source: charliebymz.com
Bikini Brief
$48
from charliebymz.com
Buy Now

Charlie by Matthew Zink Classic Brief in Buck

Buck up in the luxuriously soft Charlie by Matthew Zink Classic Brief in Buck ($52).

Image Source: charliebymz.com
Charlie by Matthew Zink Classic Brief in Buck
$52
from charliebymz.com
Buy Now

Charlie by Matthew Zink Original Long John in White

If you're going to spend all day at home, do it in Italian melange cotton in the Charlie by Matthew Zink Original Long John in White ($68).

Image Source: charliebymz.com
Charlie by Matthew Zink Original Long John in White
$68
from charliebymz.com
Buy Now

CDLP 3-Pack Boxer Trunk

Hailed by Vogue as the best men's underwear in the world, Swedish menswear dynamo CDLP promises its CDLP 3-Pack Boxer Trunk ($79 for a pack of three) is the "softer than silk, smoother than cotton" underwear of your dreams. Made sustainably out of eco-conscious Lyocell, CDLP's naturally antibacterial trunks are quickly becoming the new classic.

Image Source: cdlp.com
CDLP 3-Pack Boxer Trunk
$79
from cdlp.com
Buy Now

CDLP 2-Pack Long Johns

Designed to be worn as a single layer, CDLP 2-Pack Long Johns ($119) put a new spin on the Scandinavian classic with a better cut, breathability, and range of motion in mind.

Image Source: cdlp.com
CDLP 2-Pack Long Johns
$119
from cdlp.com
Buy Now

J.Crew Boxers in Nautical Print

With a hidden single-button fly and playful new patterns, J.Crew's new gen of boxers live up to their "unmentionables worth mentioning" tagline at an unbeatable price point, and that goes for these J.Crew Boxers in Nautical Print ($20).

Image Source: jcrew.com
J.Crew Boxers in Nautical Print
$20
from jcrew.com
Buy Now

Emporio Armani Pack of 3 Briefs With Side Logo

Cut close to the body with clean lines, the Emporio Armani Pack of 3 Briefs With Side Logo ($56 for a pack of three) skip the flashy branding and employ a low-rise, contoured pouch to cradle and cushion you down south.

Image Source: armani.com
Emporio Armani Pack of 3 Briefs With Side Logo
$56
from armani.com
Buy Now

Tom Ford Swirl Silk Boxers

We wouldn't expect anything less from Tom Ford than boxers that ooze sex appeal, and his Italian-made Swirl Silk Boxers ($295) fit the bill, velvet waistband and all. Simply said, they're the best a man can buy.

Image Source: tomford.com
Swirl Silk Boxers
$295
from tomford.com
Buy Now

Lacoste Iconic Boxer Briefs With Three-Tone Waistband

Thanks to a soft cotton-elastane blend, the subtle yet sophisticated Lacoste Iconic Boxer Briefs With Three-Tone Waistband ($29 for a pack of three, originally $43) are tailor-made to move with you.

Image Source: lacoste.com
Lacoste Iconic Boxer Briefs With Three-Tone Waistband
$29
from lacoste.com
Buy Now

Hugo Boss Three-Pack of Boxer Briefs in Stretch Cotton

Great for working out, the Hugo Boss Three-Pack of Boxer Briefs ($42 for a pack of three) are cut in breathable stretch cotton. Run, stretch, and squat-jump with a full range of movement.

Image Source: hugoboss.com
Hugo Boss Three-Pack of Boxer Briefs
$42
from hugoboss.com
Buy Now

Rufskin Wrap Royal Briefs

Rufskin plays to the contours of a man's body better than any other men's underwear brand, point-blank. Refreshingly simple and decidedly modern, the Wrap Royal Stretch-Cotton Briefs ($39) look and feel like something out of the future.

Image Source: rufskin.com
Wrap Royal Stretch-Cotton Briefs
$39
from rufskin.com
Buy Now

Rufskin Ziane Melrose Stretch Briefs

Don't knock minimalism until you try it in the sleek Rufskin Ziane Melrose Briefs ($39).

Image Source: rufskin.com
Rufskin Ziane Melrose Briefs
$39
from rufskin.com
Buy Now

Versace Jungle Print Briefs

Go with the confidence of Jennifer Lopez inadvertently inventing Google Images in the Versace Jungle Print Briefs ($125), inspired by J Lo herself.

Image Source: versace.com
Versace Jungle Print Briefs
$125
from versace.com
Buy Now

Jacquemus Blue Flower "Le Caleçon" Boxers

Born out of French fashion darling Simon Porte Jacquemus's eponymous brand, the Jacquemus Blue Flower "Le Caleçon" Boxers ($165) are straight off the Spring 2020 runway.

Image Source: ssense.com
Jacquemus Blue Flower "Le Caleçon" Boxers
$165
from ssense.com
Buy Now

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