Top TomboyX Deals & Price Drops for May 2026

Experience ultimate comfort and sustainable style with the TomboyX 6" Fly Boxer Briefs 3-Pack in Black, exclusively from TomboyX.com. These mid-length boxer briefs are designed to take you all the way, offering full coverage without sacrificing breathability. Crafted from soft, sustainable TENCEL Modal sourced from renewable beechwood trees, this eco friendly fabric feels like wearing nothing at all while delivering chafe free security. The 6 inch inseam provides a perfect balance of coverage and freedom, while the mid rise fit flatters a variety of body types. Thanks to the highly stretchy fabric blend of 95% TENCEL Modal and 5% spandex, these briefs accommodate different shapes and sizes with ease. The signature stay put silky soft waistband ensures your underwear stays in place all day, eliminating constant adjustments. Durable flatlock seams are smooth and irritation free, making these boxer briefs ideal for active lifestyles or everyday wear. Inclusive sizing from XS to 4X means everyone can enjoy the perfect fit. Machine wash cold and tumble dry low for easy care. Upgrade your underwear drawer with this three pack of versatile, sustainable briefs that combine comfort, durability, and style. Shop now at TomboyX and experience the difference of thoughtfully designed essentials. Note that this item is not eligible for Love at First Wear returns.

Experience unmatched comfort with TomboyX's 6 Fly Boxer Briefs 3-Pack in classic Black. Crafted from soft and sustainable TENCEL Modal sourced from renewable beechwood trees, these mid-rise boxer briefs feature a 6-inch inseam for full coverage without bulk. The highly stretchy fabric adapts to various body types, while smooth flatlock seams prevent chafing and irritation. A signature stay-put waistband ensures a secure fit that stays in place all day. Ideal for active lifestyles or lounging, this pack offers three pairs of chafe-free, barely-there underwear that feels like wearing nothing. Machine wash cold and tumble dry low for easy care. Inclusive sizing from XS to 4X caters to everyone. Upgrade your drawer with eco-friendly comfort from TomboyX.

The Bamboo Rib 4.5" Trunks from TomboyX in Bering Sea are your new everyday essential, redesigned for a superior fit and an unmatched feel. Crafted with a breathable, body-hugging rib construction, these trunks offer silky softness that moves with you while maintaining their shape wear after wear. The smooth, no pinch waistband stays comfortably in place, so you can focus on your day without constant adjustments. Made from a sustainable blend of 45% recycled polyester, 42% bamboo viscose, and 13% elastane, this trunk is lightweight yet opaque, providing total coverage without the bulk. The bamboo lining adds an extra layer of breathable comfort, while the fabric naturally wicks moisture and resists odors, making it perfect for active days or casual lounging. With a 4.5 inch inseam, they offer a balanced cut that works for any body type. OEKO TEX certified and available in inclusive sizing from XS to 6X, these trunks prove that comfort and style can coexist. Whether you're dressing up or winding down, the Bering Sea shade adds a tranquil vibe to your underwear drawer. Experience the difference of a trunk that stretches, recovers, and supports you exactly how you need it. Shop now at TomboyX.com and discover your new go to for everyday wear that feels as good as it looks.

Looking for the perfect everyday bikini that combines comfort, sustainability, and effortless style? The Bikini 3-Pack in Black from TomboyX is your new go to. Crafted from ultra soft TENCEL Modal sourced from renewable beechwood trees, this low rise cut delivers a barely there feel with the reliable coverage you need. The highly stretchy fabric and smooth flatlock seams move with your body without irritating or chafing, making it ideal for all day wear. Each pair features a signature stay put silky soft waistband that stays in place without digging in. Whether you are dressing up or lounging at home, this three pack offers unbeatable value and versatility. Available in inclusive sizing from XS to 4X, these bikinis are designed to flatter a wide range of body types. They are machine washable for easy care and hold up beautifully wash after wash. Experience the perfect blend of elegance, softness, and sustainability. Shop the Bikini 3-Pack today at TomboyX and upgrade your essentials with comfort you can feel good about.

Meet the 9" Boxer Briefs in Critter Board from TomboyX. If you have been searching for the longest inseam boxer that actually stays put, this is it. Designed to prevent chafing and keep you fully covered, these boxer briefs combine comfort with a clean, confident look. Crafted from our signature supersoft cotton blend, the fabric offers a gentle stretch that moves with you. The 9 inch inseam provides extra length for those who prefer more coverage or need protection against thigh rub. Our stay put waistband is engineered to stay in place without pinching, digging in, or riding up throughout your day. Flatlock seams are smooth and durable, reducing irritation and ensuring these boxers feel invisible under your clothes. The playful Critter Board artwork is an original design created by our in house team, adding personality to your everyday essentials. Available in inclusive sizing from XS to 6X, these boxer briefs are built for every body. The fabric is 95 percent cotton and 5 percent spandex, and it is OEKO-TEX Certified for peace of mind. Easy care instructions include machine washing cold and tumble drying low. Upgrade your underwear drawer with the longest, most comfortable boxer briefs from TomboyX. Experience the difference a thoughtful fit and quality materials make. Shop the 9" Boxer Briefs Critter Board at TomboyX.com today.

Say hello to our wedgie-free wonder and our most popular silhouette. It’s full coverage for your cheeks. Our supersoft cotton blend gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 2.5” inseam Signature stay-put silky soft black tomboyx waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

Our longest boxer brief, now in breathable Powermesh. Designed with a double-layer gusset to give you support where it counts while keeping everything else cool, smooth, and sheer. Perfect under layers or on its own. 82% Polyamide, 18% Elastane Powermesh (OEKO-TEX® certified) Double-layer gusset for coverage; sheer everywhere else 4-way stretch and shape retention 9" inseam, mid-rise fit Flatlock seams for smooth, chafe-free wear Signature silky-soft, stay-put waistband Machine wash cold, tumble dry low

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 4.5” inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

We’ll keep it brief - these are classic for a reason. Our supersoft, extra-breathable cotton blend is paired with a cut that won’t ride up or let you down. That’s why we think our full-coverage brief is an everyday hero. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Low rise fit Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

Finally! We borrowed all of the things that you love in our briefs and rolled them into one perfect pair - for those of us who want a little bit of everything. These briefs feature our signature flat-front, wrapped-for-comfort design with a shorter 6" inseam. The supersoft cotton blend gives just a hint of stretch to make sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 6" inseam Signature stay-put silky soft waistband 95% OEKO-TEX Certified cotton, 5% spandex Smooth, durable flatlock seams won’t irritate or chafe

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 4.5” inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 4.5” inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

These briefs feature our signature flat-front, wrapped-for-comfort design with a shorter 6" inseam. The supersoft cotton blend gives just a hint of stretch and our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 6" inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

These briefs feature our signature flat-front, wrapped-for-comfort design with a shorter 6" inseam. The supersoft cotton blend gives just a hint of stretch and our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 6" inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

Say hello to our wedgie-free wonder and our most popular silhouette. It’s full coverage for your cheeks. Our supersoft cotton blend gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Oopsie: we made this batch a bit small– we recommend sizing up one from your usual size. Can’t find your size? Check out our full assortment of perfect undies here. Mid rise fit, 2.5” inseam Signature stay-put silky soft black tomboyx waistband Smooth, durable flatlock seams won’t irritate or chafe 95% cotton, 5% spandex OEKO-TEX® certified

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Fit-tested on all body types and all our sizes Signature stay-put silky soft waistband 95% OEKO-TEX Certified cotton, 5% spandex Smooth, durable flatlock seams won’t irritate or chafe Mid rise fit, 4.5” inseam Machine wash cold, tumble dry low

Now offering our classic Bikini Style in our First Line Collection. No leaks, no mess, no worries. First Line is designed to help keep you dry and on-the-go with confidence. The First Line Period Bikini provides the highest level of absorbency and protection for your leaks, while providing a higher leg with modest coverage. With built-in leak protection for light days or incontinence, you’ll be able to relax, move, and breathe easy. Finished with naturally water resistant foldover elastic and threads. Constructed with a new and improved wider and longer pad that increases absorbency. And, now you can machine wash and dry without a fuss. First Line underwear is made with OEKO-TEX® 100 Certified fabrics which is one of the world's best-known labels for textiles tested for harmful substances. Learn more about how we avoid chemicals in our products. Fit-tested on all body types 95% OEKO-TEX Certified cotton, 5% spandex Lining: 89% Polyester, 11% Spandex Absorbs up to 8 tsps of liquid Low rise Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe Machine wash cold, tumble dry low.

Our Tucking Hipster delivers a safe, comfortable “soft tuck” via gentle compression and snug dimensions. Built in double-layered interlock polyester with one-way stretch and an extra layer of compressive mesh to hold everything in place, plus covered elastic at the leg holes guarantees all-day security. Antibacterial, odor-resistant fabric treatment ensures freshness, and less coverage in the back means a less visible line under your clothes. Fit-tested on all body types, sizes XS-4X Body: 100% Recycled polyester Lining: 84% Nylon, 16% spandex mesh Fold-over elastic on leg openings secures fit Antibacterial, odor resistant, breathable, and moisture wicking Machine wash cold, tumble dry low

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a boy short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and our signature stay-put waistband that keeps it together without pinching or riding up. Mid rise fit, 4.5” inseam Signature stay-put silky soft waistband Smooth, durable flatlock seams won’t irritate or chafe Inclusive sizing from XS-6X 95% cotton, 5% spandex OEKO-TEX® Certified Machine wash cold, tumble dry low

All-day confidence made stylish, secure, and comfortable. This high leg, mid-rise bikini-cut underwear features double-layered interlock polyester with 1-way stretch, delivering snug, secure compression while retaining breathability, moisture wicking, and quick drying performance. Antibacterial, odor-resistant fabric treatment ensures freshness, and a wider crotch than our classic bikini style delivers a more accommodating fit. Body: 100% recycled polyester Lining: 84% Nylon, 16% spandex mesh Fold-over elastic on high openings secures fit Mid-rise fit Antibacterial, odor resistant, breathable, and moisture wicking treatment Fit-tested on all body types, sizes XS-4X Machine wash cold, tumble dry low

You’ve never seen a trunk like this - the first and the best gender-neutral classic just for you. Somewhere between a short and a brief, our 4.5” trunks are everything you need. Made with supersoft cotton blend that gives just a hint of stretch and makes sure you stay comfy, while our signature stay-put waistband keeps it together without pinching or riding up. Fit-tested on all body types Signature stay-put silky soft waistband 95% OEKO-TEX Certified cotton, 5% spandex Smooth, durable flatlock seams won’t irritate or chafe Mid rise fit, 4.5” inseam Machine wash cold, tumble dry low