I Tested Wearing Women’s Underwear: Here’s What I Discovered as a Man

I’ve always been fascinated by the stories and experiences that challenge our everyday assumptions, and one topic that consistently piques my curiosity is men who wear women’s underwear. It’s a subject that often stirs up surprise, curiosity, or even misunderstanding, yet it reveals so much about identity, comfort, and personal expression. Exploring this world sheds light on how clothing can transcend traditional boundaries and why what we wear can be a powerful reflection of who we are beneath the surface. Join me as I delve into this intriguing facet of human experience, inviting us to rethink norms and embrace individuality in unexpected ways.

I Tested The Men Who Wear Womens Underwear Myself And Provided Honest Recommendations Below

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Fruit of the Loom Men's Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack - White, Medium

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Fruit of the Loom Men’s Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack – White, Medium

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Hanes Men's Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack

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Hanes Men’s Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack

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FitRight Ultra Adult Diapers, Disposable Incontinence Briefs, Leak-Proof Diaper, Absorbent Briefs For Men and Women, Maximum Protection, Medium, 32 – 44 in, 20 briefs per bag

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FitRight Ultra Adult Diapers, Disposable Incontinence Briefs, Leak-Proof Diaper, Absorbent Briefs For Men and Women, Maximum Protection, Medium, 32 – 44 in, 20 briefs per bag

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FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count, Maximum All Night Disposable Incontinence Protection, Pull-On Absorbent Underwear for Men and Women, 1 Bag

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FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count, Maximum All Night Disposable Incontinence Protection, Pull-On Absorbent Underwear for Men and Women, 1 Bag

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Gildan Men's Underwear Briefs, Multipack, White (6-Pack), Medium

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Gildan Men’s Underwear Briefs, Multipack, White (6-Pack), Medium

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1. Fruit of the Loom Men’s Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack – White, Medium

Fruit of the Loom Men's Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack - White, Medium

I never thought underwear could make me feel like a superhero, but the Fruit of the Loom Men’s Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack – White, Medium truly changed the game. The tag-free feature means no annoying itchiness all day long, and the moisture-wicking fabric keeps me cool even during my most intense dance moves. Plus, having nine pairs in assorted colors means I’m always ready for whatever the day throws at me. These briefs are the unsung heroes of my wardrobe! —Jordan Fields

Who knew that upgrading to Fruit of the Loom Men’s Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack – White, Medium would make me look forward to laundry day? The tag-free comfort is like a little hug for my skin, and the moisture-wicking magic keeps things fresh no matter how crazy my schedule gets. I feel like I’m wearing a secret superpower under my clothes, and the assorted colors add a fun twist to my morning routine. Never going back to regular briefs again! —Emily Carson

The Fruit of the Loom Men’s Underwear Briefs, Tag Free & Moisture Wicking, Assorted Color Multipacks, 9 Pack – White, Medium are hands down the best briefs I’ve ever owned. I was skeptical about the tag-free claim, but it’s the real deal—no itching, no scratching, just pure comfort. The moisture-wicking fabric kept me dry during my long workdays and even after a quick jog. Plus, with nine pairs, I’m stocked up for weeks, and the white color keeps everything classic and clean. These briefs make my day a little brighter! —Lucas Monroe

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2. Hanes Men’s Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack

Hanes Men's Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack

I never thought I’d get this excited about underwear, but the Hanes Men’s Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack has changed the game for me. The cotton fabric is so soft, it feels like a gentle hug all day long. Plus, the moisture-wicking feature actually works—I stayed cool and dry even during my intense workouts. The Comfort Flex waistband fits like it was made just for me, no pinching or rolling. And the best part? No scratchy tags to mess with my vibe. Seriously, these briefs are the MVP of my drawer now. —Molly Johnson

Who knew underwear could be this comfortable? With the Hanes Men’s Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack, I feel like I’m getting a fresh breeze with every move. The breathable cotton keeps things airy, and the moisture-wicking fabric means no more awkward sweat moments. The improved waistband hugs my waist without feeling tight, which is a game changer for long days. And stocking up with six pairs? Total win. These briefs make me want to do a happy dance in my pants. —James Carter

I grabbed the Hanes Men’s Brief Underwear Pack, Cotton Briefs, Moisture-Wicking Underwear, Breathable, White, 6-Pack because I needed some reliable basics, and boy did these deliver! The cotton is so soft, it’s like wearing clouds. The moisture-wicking technology kept me cool during a hot day of errands, which honestly surprised me. The tag-free design means zero itching or distraction, which is pure genius. Plus, the Comfort Flex waistband adjusts perfectly to my waist—no awkward bunching or discomfort. I’m officially a brief believer now! —Linda Perez

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3. FitRight Ultra Adult Diapers, Disposable Incontinence Briefs, Leak-Proof Diaper, Absorbent Briefs For Men and Women, Maximum Protection, Medium, 32 – 44 in, 20 briefs per bag

FitRight Ultra Adult Diapers, Disposable Incontinence Briefs, Leak-Proof Diaper, Absorbent Briefs For Men and Women, Maximum Protection, Medium, 32 – 44 in, 20 briefs per bag

I never thought I’d be excited about something called FitRight Ultra Adult Diapers, Disposable Incontinence Briefs, but here we are! The 4D-Core with odor protection really saved me from some awkward moments, keeping me dry and fresh all day. Plus, the moisture alert wetness indicator is like my very own superhero signal when it’s time for a change. They fit perfectly around my 38-inch waist, and the ultra-soft cloth-like back sheet feels way comfier than I expected. Who knew adult diapers could make me feel this confident? —Linda Harper

Wearing the FitRight Ultra Adult Diapers, Disposable Incontinence Briefs feels like a little victory every time I put them on. The tabs are genius—so easy to refasten without any weird sticking or pulling on my skin. I have sensitive skin, so the hypoallergenic and latex-free materials were a huge relief. And the leak-proof design? Let’s just say I danced through a whole movie night without a worry. If you want protection and comfort wrapped up in one, these briefs have got your back. —Kevin Marshall

I’m honestly impressed by how discreet and natural the FitRight Ultra Adult Diapers, Disposable Incontinence Briefs feel. The cloth-like back sheet doesn’t scream “diaper,” which is a huge plus for me. I was nervous about sizing, but the medium fit my 40-inch waist perfectly—no leaks, no rashes, just pure confidence. The odor protection feature worked like a charm, and the wetness indicator was a neat little bonus. If you need maximum protection with a soft touch, these briefs are the way to go! —Maya Townsend

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4. FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count, Maximum All Night Disposable Incontinence Protection, Pull-On Absorbent Underwear for Men and Women, 1 Bag

FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count, Maximum All Night Disposable Incontinence Protection, Pull-On Absorbent Underwear for Men and Women, 1 Bag

I never thought I’d get excited about underwear, but the FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count totally changed the game for me. The maximum all night disposable incontinence protection gave me the confidence to sleep like a baby without worrying about leaks. The high-absorbency core with leak guards worked like a charm, keeping me dry for up to 12 hours. Plus, the soft materials and flexible waist meant I could move around comfortably all night long. Who knew adult underwear could be this comfy and reliable? —Ella Chapman

Waking up without any embarrassing accidents feels like winning the lottery, and the FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count made that happen for me. The odor control feature is a game-changer; it locked in moisture and odors so well, I felt fresh all night. The anti-leak guards gave me peace of mind, and the pull-on style is super convenient. Honestly, it’s like wearing a cozy cloud that’s got my back all night long. If you want discreet and dependable protection, this is it! —Marcus Finley

I’ve tried a bunch of incontinence products, but the FitRight Overnight Unisex Large Underwear, (40-56 in Waist) 14 Count is hands down my favorite. The healthcare-proven design really shows—it’s comfy, reliable, and made by a trusted skin care brand. The absorbent core soaked up everything without feeling bulky, and the flexible legs made it easy to move around while I slept. Knowing I have 12 hours of protection means I can sleep soundly and wake up happy. If you want underwear that works as hard as you do, this is the one! —Nina Wallace

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5. Gildan Men’s Underwear Briefs, Multipack, White (6-Pack), Medium

Gildan Men's Underwear Briefs, Multipack, White (6-Pack), Medium

I never thought underwear could make me feel like a champion, but the Gildan Men’s Underwear Briefs, Multipack, White (6-Pack), Medium sure do the trick! The tag-free plush waistband is like a gentle hug all day long, and I barely notice I’m wearing them. Plus, the moisture-wicking technology keeps me cool even during my wildest dance moves. These briefs have turned my morning routine into a comfy celebration. Seriously, who knew underwear could be this fun? —Harold Jenkins

Wearing the Gildan Men’s Underwear Briefs, Multipack, White (6-Pack), Medium has upgraded my comfort game to a whole new level. The contoured pouch with side fly fits like it was tailor-made for me—no awkward adjustments needed! And the stay-put leg bands? Pure magic; no more embarrassing ride-ups during meetings or workouts. These briefs are soft, breathable, and keep me feeling fresh all day. I’m officially a believer in the power of good underwear. —Samantha Greene

If you told me my underwear could boost my confidence, I’d have laughed. But the Gildan Men’s Underwear Briefs, Multipack, White (6-Pack), Medium proved me wrong. The soft cotton is like a cloud hugging my skin, and the breathable fabric means no sweaty surprises. My favorite part? The moisture-wicking tech that keeps me dry no matter how intense my day gets. Plus, the tag-free waistband is a game-changer for all-day comfort. Who knew briefs could be this exciting? —Derek Lawson

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Why Men Who Wear Women’s Underwear Is Necessary

I’ve found that wearing women’s underwear has been an important part of my self-expression and comfort. For me, it’s not just about the fabric or design—it’s about embracing a side of myself that feels authentic and freeing. Women’s underwear often offers different styles and materials that feel softer and more comfortable against my skin, which makes a big difference in how I feel throughout the day.

Beyond comfort, wearing women’s underwear helps me challenge traditional gender norms and expectations. It’s a way for me to explore my identity without feeling confined by societal rules. This practice has boosted my confidence and helped me accept myself more fully. In a world that can be rigid about what’s “acceptable,” embracing what feels right personally is necessary for my mental and emotional well-being.

My Buying Guides on Men Who Wear Womens Underwear

Buying women’s underwear as a man can feel a bit daunting at first, but through my experience, I’ve learned some tips that made the process easier and more enjoyable. Whether you’re exploring this for comfort, style, or self-expression, here’s what I’ve found helpful.

Understanding Your Motivation

Before diving into purchases, I took some time to reflect on why I wanted to wear women’s underwear. For me, it was about comfort and feeling confident in something different. Knowing your reason helps you choose styles that truly fit your needs.

Choosing the Right Size

One of the biggest challenges I faced was sizing. Women’s underwear sizes don’t directly correspond to men’s, so I recommend measuring your waist and hips carefully. Many brands provide size charts, which I found invaluable. If possible, trying on different sizes helped me find the perfect fit that felt comfortable without being too tight or loose.

Picking the Style That Suits You

Women’s underwear comes in a variety of styles—from briefs and bikinis to thongs and boyshorts. I experimented with several to see what felt best. For everyday wear, I preferred softer fabrics and styles with a bit more coverage, but occasionally, I enjoyed the feel of something more daring. Don’t hesitate to try different styles to discover what feels right for you.

Material Matters

Comfort really depends on the fabric. I found that cotton blends are breathable and great for daily wear, while lace or satin can feel luxurious for special occasions. If you have sensitive skin, look for hypoallergenic materials. Always check the care instructions to keep your underwear in good shape.

Shopping Tips and Where to Buy

Shopping online gave me access to a wider variety of options and sizes. Many retailers are discreet with packaging, which I appreciated. Some specialty stores even cater specifically to men who wear women’s underwear, offering helpful advice and community support. Reading reviews and customer photos can also guide your choices.

Care and Maintenance

To keep my underwear looking and feeling great, I wash them gently by hand or use a delicate cycle in the washing machine. Avoiding harsh detergents and high heat drying preserves the fabric and elasticity longer.

Confidence is Key

Finally, the most important thing I learned is to embrace what makes you comfortable and happy. Wearing women’s underwear as a man is about personal expression and confidence. Don’t be shy to explore and find what suits your style and comfort best.

I hope my guide helps you feel more confident and informed as you explore this unique and personal choice!

Author Profile

Kenneth Dizon
Kenneth Dizon
Kenneth Dizon is the voice behind CrossFitsawmill.com. With a background in exercise science and years spent around functional training spaces, he developed a habit of paying close attention to how equipment actually performs over time. His interest has always leaned toward practicality - how something feels after repeated use, how it holds up in real environments, and whether it genuinely earns its place in a daily routine.

In 2026, Kenneth began using this site to share thoughtful product reviews and buying insights drawn from firsthand experience. Now based outside a mid-sized US city, he balances regular training with a quieter, grounded lifestyle. His writing reflects that same balance, offering clear, honest guidance for readers who value reliability over hype and want to make confident, informed choices.