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26 Fun & Sexy Valentine’s Day Underwear for Men that You Both Can Enjoy

Attention all lovebirds and mischief-makers! This February 14, let your imagination run wild with these 26 fun and sexy Valentine’s Day underwear for men. Whether you’re searching for a playful surprise for your partner or seeking an intimate piece that will ignite the passion in your relationship, we’ve handpicked a range of options that will make hearts skip a beat. Ready to unleash your inner vixen and make this V-Day an affair to remember?

Sexiest Men’s Underwear for Valentine’s Day

Calvin Klein Stretch-Cotton Valentine’s Day Brief

Sexiest Men's Underwear for Valentine's Day

These Valentine’s briefs are the perfect blend of comfort and sexiness, guaranteed to make your man feel like a total heartthrob. With their playful heart patterns and intricate lace trim, these briefs are designed to make hearts race. The soft and breathable fabric ensures a cozy fit, while the form-fitting silhouette accentuates all the curves he has. 

MeUndies Men’s Jockstrap

Sexiest Men's Underwear for Valentine's Day

Want to surprise your man with a gift that’s both alluring and comfortable? Look no further than this black jockstrap. It’s the perfect example of how less can be oh-so-much more! With a range of sizes and colors, all crafted with ultra-soft, sustainable beachwood fibers, this jockstrap is easily one of the sexiest men’s mens Valentines boxers.

Lovehoney Lipstick Kisses Boxer Shorts

Sexiest Men's Underwear for Valentine's Day

Ready to turn up the heat this Valentine’s Day? These sheer boxer briefs are the ultimate gift for your man. Their alluring design leaves little to the imagination, creating a seductive vibe. The hip-hugging fit not only brings out his best features but also adds a touch of confidence to his stride.

Calvin Klein Micro 3 Pack Hip Brief

Sexiest Men's Underwear for Valentine's Day

This Calvin Klein brief is a must-have for every modern man, a gift that combines style and sensuality. Made from silky soft microfiber, it provides a luxurious feel that he’ll love. The contoured pouch provides support and enhances his natural shape. With an elasticated waistband and impeccable craftsmanship, this product is as comfortable as it is sexy.

Urban Outfitters Kiss Me Boxer Brief

Sexiest Men's Underwear for Valentine's Day

Take your intimate moments to the next level with this boxer from Urban Outfitters. The bold “Kiss Me” print adds a touch of excitement and playfulness, while the boxer brief style ensures a comfortable and flattering fit.  Moreover, these boxer briefs are soft against the skin, allowing him unrestricted movement and comfort.

Apparel Men’s Baby Rib Brief

Sexiest Men's Underwear for Valentine's Day

Made with soft and stretchy fabric, these seductive briefs are designed to hug his curves in all the right places. With a range of vibrant colors like Ruby, Fuchsia, and Baby Pink, you can choose the shade that sets the mood just right. Trust us, this V-Day present will not only make him feel sexy but will also ignite the passion between you two. 

Hanro 2-pack Brief

Sexiest Men's Underwear for Valentine's Day

These seductively stylish briefs that come in navy and red are sure to set the mood and make your man feel like a total stud. The soft elastic waistband with the embossed HANRO logo adds a touch of luxury, while the fine rib knit and comfortable lining ensures a snug and flattering fit. 

Tom Ford Velvet-Trimmed Silk-Satin Boxer Shorts

Sexiest Men's Underwear for Valentine's Day

These luxurious boxer shorts are the epitome of sophistication and sexiness in men’s Valentine boxers. The smooth silk satin fabric feels like a dream against the skin, while the velvet trim adds a touch of opulence. Whether you’re planning a romantic evening or a passionate night in, these boxer shorts will undoubtedly spice up your bedroom actions!

Calvin Klein Low-Rise Trunks

Sexiest Men's Underwear for Valentine's Day

These trunks are not just a gift; they’re an invitation to explore and ignite your bedroom’s desire flames. The low-rise fit and contour pouch will enhance your man’s features. The fabric is so comfortable he won’t want to take them off, and the bold black color adds a touch of edginess and mystery. 

Jambys Flamingo Boxers

Sexiest Men's Underwear for Valentine's Day

Imagine a gift beyond the ordinary – enter Jambys’ boxers with pockets. They’re not just your average loungewear; they’re a thoughtful addition to his downtime experience. These unisex boxers, a hybrid of underwear and basketball shorts, bring a new level of comfort and versatility. 

Your man can relax in style, whether chilling at home or going for a quick outdoor activity. It’s a perfect match for both of you, adding an extra connection layer to your celebration.

Savage X Satin Boxers

Sexiest Men's Underwear for Valentine's Day

Hello, beautiful! If you’re searching for a Valentine’s Day gift that’s both practical and sexy, consider these Savage X satin boxers for your special man. Imagine him unwrapping this stylish package and discovering the luxurious feel of satin against his skin. It’s a thoughtful way to add a touch of romance to his daily routine.

Lunya Men’s Washable Silk Boxers

Sexiest Men's Underwear for Valentine's Day

If your husband or boyfriend is wondering what to wear on Valentine’s Day, present him with these silk boxers that will elevate his gentlemanly look to another level. The rich wine color exudes class and allure, while the silk fabric adds a layer of sophistication.  

Envision him leisurely lounging in these boxers, feeling pampered and at ease. These boxers are chic and a seamless fusion of practicality and romance for that special man in your life!

2Xist Men’s 3-Pack Stretch Core No-Show Briefs

Sexiest Men's Underwear for Valentine's Day

If you’re on the hunt for a Valentine’s gift that keeps both fashion and functionality in mind, these 2Xist briefs from Freshpair are a winner. The stretchy fabric ensures a perfect fit, while the no-show design allows him to wear them discreetly under any outfit. Let him know that you appreciate his sense of style and want him to feel great every day with this present.

Cocksox Sexy Men’s Red Thong

Sexiest Men's Underwear for Valentine's Day

Ignite the flames of desire this Valentine’s Day with a gift that will make his heart race and his senses come alive. This red thong from Cocksox is not just underwear; it’s an invitation to explore new levels of intimacy together. Its form-fitting design and attention to detail will draw the focus to his natural assets, while the soft and breathable fabric will provide ultimate comfort. 

Read More: 42 Valentine’s Day Outfit Ideas For Your Date Night

Hot and Funny Valentine’s Day Underwear for Men

“The Right Reasons” Rose Pouch Underwear Briefs

Hot and Funny Valentine's Day Underwear for Men

On this special day, give your man a gift that will make him laugh and feel loved at the same time. These rose pouch underwears are like a bouquet of roses for his… well, you know. With their playful rose pattern and innovative pouch design, these briefs will keep everything in place while adding a touch of whimsy to his wardrobe. Show your man that you have a good sense of humor with this unexpected gift!

Show Me Your Bobbers I’ll Show You My Pole Men’s Boxer

Hot and Funny Valentine's Day Underwear for Men

Spice things up with a gift that’s bound to bring a smile to your man’s face on this day of love. These boxers offer a good laugh and a touch of intimacy that’s perfect for couples who appreciate humor in their relationship. It’s a fun and light-hearted way to celebrate your connection, making it an ideal and funny gift for your anniversary.

Old Navy Printed Soft-Washed Boxer Shorts

Hot and Funny Valentine's Day Underwear for Men

Oh, look! Heart-shaped patterns on shorts are a perfectly alluring gift that a lady surprises her man. The elasticized waistband ensures a perfect fit that accentuates his waistline, while the inseam hits high on the thigh, revealing a tantalizing glimpse of skin. This sexy and playful gift will make him feel incredibly desired, setting the stage for a night of passion.

Custom Face Men’s Boxer Shorts

Hot and Funny Valentine's Day Underwear for Men

Searching for a Valentine’s Day gift that’s as cheeky as your love? These personalized face photo boxer shorts from Loveable are the answer. He could be grinning from ear to ear as he unwraps a pair featuring your face, complete with a cheeky smile and hands-on-his-butt charm. It’s a playful and intimate gesture that adds a touch of fun to your celebration, proving that love can be both personal and hilarious.

Shinesty Candy Hearts Hammock Pouch Underwear Briefs

Hot and Funny Valentine's Day Underwear for Men

Love and laughter go hand in hand, especially on Valentine’s Day. These undies are the secret weapon you need for a night of passion and playfulness. With their cute candy heart prints and comfortable pouch, they’ll make your man feel supported and oh-so-sexy. So, it’s time for him to slip into these naughty briefs and enjoy some equally hot and amusing Valentine’s Day games for adults together.

Custom Face and Money Boxer Brief

Hot and Funny Valentine's Day Underwear for Men

If you’re on the prowl for a Valentine’s Day gift that’s as hilarious as it is unforgettable, dive into the world of absurdity with this unique custom boxer brief. Imagine the laughter and the twinkle in his eye as he sees his own face playfully mingling with a money print on these unique boxers! These boxers will kindle the flames of laughter and create a Valentine filled with shared joy and intimacy.

MyFaceBoxer Custom Face Briefs

Hot and Funny Valentine's Day Underwear for Men

Want to make your presence felt in a fun and unexpected way this romantic Cupid Day? And the personalized photo briefs let you do just that. Upload a photo and witness it transform into custom underwear, ensuring your Valentine carries your essence wherever they wander. It’s a quirky, delightful gift that promises laughs and adds a personalized touch to your celebration.

J.Crew Printed Boxer Briefs

Hot and Funny Valentine's Day Underwear for Men

Why wait for Cupid’s arrow when you can make your own love statement? Gift your man these vibrant heart-printed boxers made from the softest cotton reminiscent of his favorite T-shirt. It’s a guaranteed love-infused Valentine’s Day surprise!

“I licked It… So It’s Mine” Custom Face Boxer

Hot and Funny Valentine's Day Underwear for Men

Hey, lovebird! Ditch the ordinary this Valentine’s Day and opt for a gift that’s as cheeky as your love. Loveable’s “I licked it, so it’s mine” boxers are here to steal the show. The custom faces make them one-of-a-kind, and he’ll feel loved and cherished every time he puts them on. Give him a gift that’s as unique and special as your relationship.

Gap White Printed Boxer with Red Hearts

Hot and Funny Valentine's Day Underwear for Men

Imagine how cute your man looks when wearing this bright heart mens Valentines boxers. Crafted from gentle, lightweight fabric and equipped with a flexible waistband, he’ll find comfort in this pair that transcends seasons. A “sexy” night on Valentine’s Day will be more interesting thanks to this short, adding more laughter when seeing it.

Roller Rabbit Men’s Hearts Boxer Set

Hot and Funny Valentine's Day Underwear for Men

How about a more lovely and “sexy” look with this little heart-shaped short? These charming and adorable undergarments, crafted from 100% cotton, are not just made for the special day but are sure to sprinkle charm and joy all year round. Show your man that some gifts are meant to be cherished every day!

“The Hot-Blooded Handbook” Valentine Pouch Underwear

Hot and Funny Valentine's Day Underwear for Men

Ignite the passion this V-Day with this daring and seductive underwear! This boxer features a unique pouch design that provides exceptional support and promotes his natural assets. Show your adventurous side and let him know you’re ready to embark on a passionate journey with this bold and alluring gift.

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Final Thought

So, there you have it – 26 tantalizing picks of Valentine’s Day underwear ideas for men to make this day unforgettable! Whether you’re leaning towards bold and sexy or opting for witty and cute, these undergarment options are sure to add a playful spark to your celebration. Remember, it’s not just about the garments; it’s about the shared moments, the laughter, and the connection. Happy Valentine’s Day!

Blake Simpson

Hi, I’m Blake from Loveable. I help people find perfect gifts for occasions like anniversaries and weddings. I also write a blog about holidays, sharing insights to make them more meaningful. Let’s create unforgettable moments together!

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