The Best Sexy Men's Underwear for Valentine's Day and Beyond

These seductive and funny picks are entirely Valentine's-worthy.
Men's checkered Valentine's Day Underwear
Monica Mercuri - The Knot Assistant Commerce Editor
Monica Mercuri
Monica Mercuri - The Knot Assistant Commerce Editor
Monica Mercuri
Assistant Commerce Editor
  • Monica writes articles for The Knot Worldwide, specializing in e-commerce content
  • Before joining The Knot Worldwide, Monica was an assistant style and market editor at House Beautiful
  • Monica holds a bachelor's degree in journalism and mass communication from George Washington University's School of Media and Public Affairs
Updated Jan 12, 2022
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Valentine's Day 2022 (FYI: Monday, February 14) is just around the corner. And if you want to celebrate with some new V-Day underwear, we've got you covered. Sure, shopping for undies can sometimes feel like a chore, but for special occasions, it's actually pretty fun. To help, we've narrowed down the best men's underwear to impress your love (or yourself) this Valentine's Day.

Keep scrolling for the sexiest picks inspired by the day of love—from heart-print boxers to cozy briefs and statement-making thongs. And, if you like the idea of matching with your partner, check out our favorite couples' underwear sets. (Don't forget: Underwear can be an excellent Valentine's Day gift too!)

Shop our favorites:

Sexy Valentine's Day Underwear

Valentine's Day is a great opportunity to switch things up. You can show more skin, introduce a new material (like silk or lace) or experiment with a new fit. (Of course, it's also perfectly fine to buy something you're already familiar with.) Check out our favorite sexy men's boxers, briefs, thongs and more.

Cozy Satin Boxers

Red Valentine's Day Satin Boxers

You'll love how silky soft these Valentine's Day boxers feel. Buy an extra pair for your partner so you can relish in the coziness together. The Goji Berry Red or Hot and Heavy Pink are perfect for V-Day.

Classic Low-Rise Trunks

Red Valentine's Day Low-Rise Trunk

Calvin Klein is known for its sexy men's underwear. Exhibit A: this sleek low-rise trunk. Made from an ultra-soft and moisture-wicking material, it's a classic design you'll wear on the regular.

Sheer Lace Boxers

Black lace boxers

Now here's a pair of V-Day underwear that pulls out all the stops: mini-length lace boxers. What's not to love about lace? It's sheer, stylish and super steamy. You'll thank yourself later.

Casual V-Day Thong

Casual Valentine's Day Thong

Thongs aren't just for Valentine's Day. After you try one, you might want to add it to your everyday rotation. This pick is made from sustainably sourced beechwood fibers (in other words, it's irresistibly soft). Choose Cabernet Red for a classic V-Day look.

Iridescent Briefs

Iridescent Savage X Fenty briefs

This sensual Savage X Fenty underwear is a real winner when it comes to sexy men's briefs. It has an iridescent waistband for festive flair and a contour pouch for extra comfort. Pick up the matching jock strap for even more V-Day fun.

Checkered-Silk Boxers

Lahgo washable silk checkered boxer

We're big fans of Lahgo's washable silk—it's equal parts soft and sexy. This checkered-print boxer will feel insanely luxurious as soon as you slip it on. Plus, the Rich Burgundy color is undeniably on theme for Valentine's Day.

Ribbed Briefs

Soft pink high-cut underwear brief

For another sexy option, try this high-cut underwear brief with cozy ribbing. The fabric provides additional stretch and comfort—ideal for future wear. This enticing Valentine's Day underwear comes in Blush, White and Black.

Sexy Jockstrap

black sexy jock strap

Everyone can agree that jockstraps are sexy. They're also supportive, comfortable and make your butt look really good. Choose from six solid colors, including Dark Sapphire and Cabernet, or from a wide assortment of playful prints.

Mesh Boxer Shorts

red mesh boxer shorts

Leave nothing to the imagination with these transparent Valentine's Day boxer shorts. The microfiber waistband and darted pouch provide ample support and comfort. Wear this sheer underwear all day and night—you won't regret it.

Silk-Satin Boxer Shorts

pink silk boxer shorts

You'll feel like royalty in these silk-satin boxer shorts. The material combines the luster of silk with stretchy, lightweight goodness. Plus, there's a soft velvet trim emblazoned with Tom Ford's logo. (So basically, this is really fancy underwear.)

Fun Valentine's Day Underwear

Who says silly can't be sexy? Valentine's Day is the perfect excuse to play around with fun prints and sets. Here are some of our favorite styles that don't take themselves too seriously.

Heart-Print Boxer Briefs

heart-print boxer briefs

In honor of the day of love, these playful heart-printed briefs are totally on-theme. With a soft flex fabric and an anti-roll waistband, they're perfectly suited for Valentine's Day and casual wear.

Emoji Briefs

Innuendo-inspired emoji briefs

What do you get when you put the most scandalous emojis together? These innuendo-inspired briefs. They'll add much-appreciated humor and laughs to your Valentine's Day.

Custom Briefs

custom boxer briefs

Your partner will get a good chuckle out of these custom boxer briefs, which come cheekily patterned with a photo of their face. Simply add the underwear to your cart, check out and submit a picture of your S.O. (Pro tip: Buy early to ensure they arrive before V-Day).

Black Heart-Print Briefs

Black Heart-Print Briefs

Want to pay tribute to Valentine's Day without going overboard? These subtle heart-print briefs should do the trick (and they're super stretchy too).

Candy Hearts Boxers and Sock Set

Candy Hearts Boxers and Sock Set

Match your boxers and socks with this playful Valentine's Day set featuring tiny (and suggestive) candy hearts. It's also a funny Valentine's Day gift.

Lipstick-Printed Shorts

Lipstick-Printed Shorts

Nothing says "kiss me" like these frisky lipstick boxer shorts. Aside from being seductive, they're also breathable, soft and stretchy. And did we mention they're slightly sheer? Say hello to your favorite sexy-meets-silly Valentine's Day boxer.

Punny Plaid Briefs

Punny Plaid Briefs

Go "bear naked" with these plaid boxer briefs (complete with a bear on the rear). They're a foolproof pick for Valentine's Day (and everyday winter wear).

Love Doctor Set

Love Doctor Set

Channel your inner Doctor Love with this sexy costume set. It comes with tight white boxer shorts and a toy stethoscope for role-play. You'll definitely make your partner's heart beat faster.

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