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Updated Mar 17, 2025The Sexiest Men's Underwear for Valentine's Day and Beyond
These seductive picks are entirely Valentine's-worthy.
Photos, left to right: Gap, Urban Outfitters
With Valentine's Day quickly approaching on Wednesday, February 14th, you may be on the search for something special for your Valentine. Sure, flowers and chocolate are great, but this year, why not get them a gift they can enjoy all year round? We've rounded up 19 sexy men's Valentine's Day underwear that will make the perfect gift for your partner—plus, you'll love the way they look in them, so consider it a gift to yourself too.
Keep scrolling to discover our top picks for the holiday, with options in every style including boxers, briefs, and more. Then, head over to our roundup of Valentine's Day lingerie to find a little something for her. For more inspiration on what to get that special someone, check out our complete Valentine's Day gift guide.
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Valentine's Day Boxers and Boxer Briefs
If you're looking for something festive to take you from date night to late night this Valentine's Day, you're in luck. There's plenty of enticing options available from all your favorite brands. Check out these sexy men's boxers and boxer briefs.
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Urban Outfitters Kiss Me Boxer Brief
They say communication is key in every relationship, and luckily, these boxer briefs tell them exactly what you want. Choose from two Valentine's Day-worthy colorways, including red and pastel pink.
Size Range: S - L
Gap Printed Boxers in Red White Heart
Whether your Valentine prefers to wear their heart on their sleeve or under their clothes, we think they'll love these classic boxers. Made from soft, lightweight fabric and featuring a stretchy wasitband, they'll be reaching for this comfortable pair all year round.
Size Range: XS - XXL
J. Crew Printed Boxers in Heart Arrow Navy Red
Don't wait to be struck by Cupid's arrow– take matters into your own hands by gifting them these adorable heart printed boxers. Made from cotton that feels as soft as their favorite T-shirt, this is a gift they're guaranteed to love.
Size Range: XS - XXL
Lunya Men's Washable Silk Boxers in Calliope Wine
Made from uniquely-crafted (and irresistibly touchable) 100% silk, these boxers have date night written all over them. Oh, and did we mention they're machine washable? You're going to want to get your hands on these this Valentine's Day (litterally).
Size Range: S - XXL
MeUndies Perfect Pairing Boxer Briefs
Wine plus cheese equals the perfect pairing. Well, *almost* as perfect as you and your Valentine. Cozy up in these fun printed boxers– available in a wide range of sizes and prints, including other V-day options like 'Racing Hearts' and 'U Up?'.
Size Range: S - 4XL
Roller Rabbit Mens Hearts Boxer Set
You simply can't go wrong with the classics. These adorable heart-printed boxers, made from 100% cotton, were practically made for the day of love (but we think he'll love them all year round).
Size Range: XS - XXL
Jambys Unisex Boxers in Flamingo/Taffy
Boxers with pockets? Talk about a gift that keeps on giving. As a hybrid between underwear and basketball shorts, Jambys' unisex boxers are ideal for matching with your partner. Check out our roundup of matching couples underwear for more inspo.
Size Range: XS - 3XL
Savage X Satin Boxers Goji Berry Red
Your Valentine is sure to be looking sultry in these sleek, satin boxers from Savage X Fenty. Available in a wide variety of sizes and colors, they're the perfect pick for Valentine's Day and beyond.
Size Range: XS - 3XL
Old Navy Printed Soft-Washed Boxer Shorts in Pink Lollipop
So, you're a *sucker* for love? Let them know with these lollipop-printed boxer shorts. With a wide range of sizes and styles to choose from, all under $15, you really can't go wrong.
Size Range: XS - 4XL
Lovehoney Lace Boxer Shorts in Black
These sheer boxer briefs leave little to the imagination—and perhaps that's something you'll appreciate this Valentine's Day. Their hip-hugging fit makes for a sexy look that's great for spicing things up.
Size Range: S - XL
Tom Ford Velvet-Trimmed Silk Satin Boxer Shorts in Pink
If you're planning to dress to the nines this Valentine's Day, you'll need a pair of boxers to match. These velvet-trimmed silk satin boxers have luxury written all over them. Choose from multiple colors including Pink, Burgandy and more.
Size Range: S - XXL
Silk-Satin Boxer Shorts
Having trouble telling them how you feel? Say it with a pair of personalized boxer shorts. Made from 100% lightweight cotton, these soft and breathable boxers can be customized with a message of your choosing.
Size Range: S - XXL
Sexy Men's 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. Sounds tempting? We think you'll love these sexy men's underwear picks.
MeUndies Briefs in U Up?
Let's be real: Your Valentine deserves more than just a spicy text message. Luckily, we found a pair of briefs that will get the same points across. You're welcome.
Size Range: S - 4XL
Calvin Klein Intense Power Micro 3 Pack Hip Brief
There's nothing quite as alluring as the color red. It's a classic—just like Calvin Klein briefs. This Valentine's Day, you can't go wrong with a multi-pack of micro hip briefs in a variety of colors. This pack comes with red, white and off-white.
Size Range: XS - XXL
Lovehoney LHM Red Lace Thong
Their *assets* will be on full display in this cheeky micro thong. Delicate lace detailing with a supportive shape underneath makes this the best way to mix things up this Valentine's Day. Looking for a little red lace for the lady in your life? Check out this round-up of sexy and affordable lingerie.
Size Range: S/M - XXL
Calvin Klein Stretch-Cotton Valentine's Day Briefs
This pair of cotton briefs has Valentine's Day written all over them. Your partner will L-O-V-E the comfort they provide—and you'll love how great they look in them.
Size Range: S - L
Shinesty Hammock Pouch Underwear Briefs in Candy Hearts
These colorful candy-printed boxer briefs are guaranteed to satisfy your sweet tooth this holiday. Your partner will get a kick out of the spicy messages hidden in each of the conversation hearts. Plus, Shinesty's advanced technology ensures that they'll feel comfortable and confident while wearing them.
Size Range: S - 2XL
MeUndies Jockstrap in Black
Sometimes less is more, and this sexy black jockstrap is certainly a testament to that. Choose from a wide variety of sizes and colors, all made from ultra-soft sustainable beachwood fibers.
Size Range: S - 4XL
MyFaceBoxer Custom Face Briefs
Wishing your partner could take you with them everywhere they go? Well, with these personalized photo briefs, they can. MyFaceBoxer allows you to upload a photo of your choice to be featured on a pair of custom underwear. Your Valentine is bound to get a good laugh out of this unique gift.
Size Range: S - XXL
Los Angeles Apparel Men's Baby Rib Brief in Fuchsia
For a look that's guaranteed to make you *blush*, you can't go wrong with these vintage-inspired pink briefs. This enticing Valentine's Day pick comes in 23 vibrant color options.
Size Range: 0 - 4
