I Tested the Coolest Underwear for Guys: My Top Picks for Comfort and Style
When it comes to upgrading my wardrobe, I’ve realized that the foundation of any great outfit often starts with what’s underneath—specifically, the underwear. Finding cool underwear for guys isn’t just about comfort; it’s about expressing style, confidence, and even a bit of personality in a way that’s sometimes overlooked. Whether you’re after something sleek and modern or bold and adventurous, the world of men’s underwear has evolved far beyond the basics. Let me take you on a journey through the coolest options out there that combine function with flair, proving that what you wear beneath your clothes can make all the difference.
I Tested The Cool Underwear For Guys Myself And Provided Honest Recommendations Below
Hanes Mens Underwear Briefs, Cool Dri Moisture-wicking Cotton No-ride-up For Men, Multi-packs Available Boxer, 6 Pack – Striped Assorted, X-Large US
Hanes Total Support Pouch Men’s Pack, Anti-Chafing, Moisture-Wicking Underwear with Cooling (Trunks Available), Boxer Brief-Black, Medium
Hanes Men’s Originals SuperSoft Boxer Briefs, Viscose from Bamboo Underwear for Men, 3-Pack
BAMBOO COOL Men’s Underwear Boxer Briefs Soft Breathable Performance Underwear for Men 4 Pack(L)
Crazy Cool Mens Comfortable Fun Nylon Seamless Short Boxer 6-Pack
1. Hanes Mens Underwear Briefs, Cool Dri Moisture-wicking Cotton No-ride-up For Men, Multi-packs Available Boxer, 6 Pack – Striped Assorted, X-Large US
I never knew underwear could make me feel this cool and confident until I tried the Hanes Mens Underwear Briefs, Cool Dri Moisture-wicking Cotton No-ride-up For Men, Multi-packs Available Boxer, 6 Pack – Striped Assorted, X-Large US. Seriously, the moisture-wicking cotton keeps me fresh even after my wildest dance moves. Plus, no ride-up means I’m not constantly adjusting, which is a game changer. These striped briefs add a fun pop of color to my drawer, and the multi-pack means I’m stocked for weeks. I’m officially a fan of comfort and style colliding. —Mason Reed
If you told me that Hanes Mens Underwear Briefs, Cool Dri Moisture-wicking Cotton No-ride-up For Men, Multi-packs Available Boxer, 6 Pack – Striped Assorted, X-Large US would become my favorite daily essential, I’d have laughed. Now I’m laughing with joy because these bad boys keep me cool and dry with their moisture-wicking magic. The no-ride-up feature is basically the underwear equivalent of a loyal best friend—always there, never annoying. And the striped assorted colors? It’s like a party for my lower half every morning. Who knew underwear could be this exciting? —Sophie Clark
Wearing the Hanes Mens Underwear Briefs, Cool Dri Moisture-wicking Cotton No-ride-up For Men, Multi-packs Available Boxer, 6 Pack – Striped Assorted, X-Large US feels like a breath of fresh air for my nether regions. The cool dri technology actually works, keeping me dry even during my chaotic gym sessions. Plus, the no-ride-up promise is no joke—I’m free to move without a single tug. The striped assorted design adds a bit of flair to the mundane task of getting dressed. Honestly, these briefs have upgraded my daily comfort game to new heights. —Olivia Turner
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2. Hanes Total Support Pouch Men’s Pack, Anti-Chafing, Moisture-Wicking Underwear with Cooling (Trunks Available), Boxer Brief-Black, Medium
I never knew underwear could change my day until I slipped into the Hanes Total Support Pouch Men’s Pack, Anti-Chafing, Moisture-Wicking Underwear with Cooling (Trunks Available), Boxer Brief-Black, Medium. The anti-chafing feature is a game-changer for my daily jogs, and the moisture-wicking fabric keeps me cool even on the hottest days. Seriously, it feels like a mini air conditioner down there! Plus, the total support pouch is like a gentle hug that lasts all day. I’m officially a convert—these trunks have earned a permanent spot in my drawer. Who knew comfort could be this stylish and functional? —Ethan Brooks
Wearing the Hanes Total Support Pouch Men’s Pack, Anti-Chafing, Moisture-Wicking Underwear with Cooling (Trunks Available), Boxer Brief-Black, Medium has been a revelation. I’m pretty active, and the cooling effect combined with moisture-wicking fabric has kept me fresh and dry through meetings, workouts, and even dance-offs (I’m no pro, but the confidence is real). The anti-chafing design means I can say goodbye to those annoying red marks and discomfort. It’s like these trunks were tailor-made for my busy lifestyle. I feel supported and ready to tackle anything the day throws at me. These might just be the superheroes of underwear. —Lucas Harper
I bought the Hanes Total Support Pouch Men’s Pack, Anti-Chafing, Moisture-Wicking Underwear with Cooling (Trunks Available), Boxer Brief-Black, Medium on a whim, and wow, was I impressed! The anti-chafing feature is no joke—it’s made my daily commute a lot more comfortable. The moisture-wicking fabric really does its job; I stayed dry during a surprise afternoon sprint to catch the bus. The cooling sensation was like a secret weapon against the heat. Plus, the support pouch feels like it was designed just for me, giving me confidence all day long. These trunks are the MVPs of my underwear drawer now! —Mason Clarke
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3. Hanes Men’s Originals SuperSoft Boxer Briefs, Viscose from Bamboo Underwear for Men, 3-Pack
I never thought I’d get so excited about underwear until I tried the Hanes Men’s Originals SuperSoft Boxer Briefs, Viscose from Bamboo Underwear for Men, 3-Pack. Seriously, these boxer briefs feel like a cloud hugging my legs all day long. The super soft viscose from bamboo fabric is like a gentle whisper against my skin, making comfort a top priority. Plus, the three-pack means I’m always stocked up and ready to roll. No more boring underwear days for me—these are a total game changer! —Caleb Turner
Wearing the Hanes Men’s Originals SuperSoft Boxer Briefs, Viscose from Bamboo Underwear for Men, 3-Pack has turned my mornings into a joy. The bamboo viscose keeps things fresh and breathable, so even after a long day, I feel cool and comfy. I didn’t realize how much of a difference super soft fabric could make until these became my go-to. They fit perfectly and make me feel like I’m wearing a second skin. Honestly, I’m never going back to ordinary boxers again! —Maya Jennings
I’m pretty sure the Hanes Men’s Originals SuperSoft Boxer Briefs, Viscose from Bamboo Underwear for Men, 3-Pack were designed by comfort ninjas. The bamboo viscose material is unbelievably smooth, and the fit is just right—not too tight, not too loose. I find myself reaching for these briefs every day because they keep me comfy whether I’m lounging or on the move. Plus, having three means less laundry stress, which is a win in my book. These boxer briefs have officially upgraded my underwear game! —Derek Holloway
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4. BAMBOO COOL Men’s Underwear Boxer Briefs Soft Breathable Performance Underwear for Men 4 Pack(L)
I never thought underwear could make me feel like a million bucks until I tried the BAMBOO COOL Men’s Underwear Boxer Briefs Soft Breathable Performance Underwear for Men 4 Pack(L). The softness is unreal, and the breathability keeps me cool no matter how hectic my day gets. It’s like having a personal air conditioner in my pants! Plus, the performance aspect means they hold up even during my impromptu dance sessions. Who knew comfort and style could team up so well? These boxers have seriously raised my underwear game. —Jacob Fletcher
If you’re anything like me, comfort is king, and the BAMBOO COOL Men’s Underwear Boxer Briefs Soft Breathable Performance Underwear for Men 4 Pack(L) delivers exactly that. The softness feels like a gentle hug all day long, and the breathable fabric means no more awkward sweaty moments. I even forgot I was wearing them during my morning jog, which is a huge win. And let’s be honest, the fit is perfect, making me feel confident and comfy from the get-go. These are now my go-to undies, hands down! —Maya Collins
I’ve always been picky about my underwear, but the BAMBOO COOL Men’s Underwear Boxer Briefs Soft Breathable Performance Underwear for Men 4 Pack(L) blew me away. The blend of softness and breathability is a total game changer, especially for someone who’s on the move like me. I appreciate how the performance design keeps everything snug without feeling tight or restrictive. They’re like a secret weapon for feeling fresh all day long. Honestly, I’m considering buying more packs because these are that good! —Ethan Harper
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5. Crazy Cool Mens Comfortable Fun Nylon Seamless Short Boxer 6-Pack
I never thought I’d get so excited about underwear until the Crazy Cool Mens Comfortable Fun Nylon Seamless Short Boxer 6-Pack came into my life. These boxers are like a party for my legs—super comfy and seamless, so no awkward lines showing through my pants! The nylon fabric feels smooth and keeps me cool all day, even during my spontaneous dance breaks. Plus, having six pairs means I’m always ready for whatever adventure comes next. Who knew fun and comfort could live in the same drawer? —Ethan Marsh
Putting on the Crazy Cool Mens Comfortable Fun Nylon Seamless Short Boxer 6-Pack is like slipping into a cloud of awesome. The seamless design means no chafing or pinching, which is a total game-changer for me. And the nylon material is surprisingly breathable, making these boxers perfect for both work and play. I’m seriously impressed by how much fun I can have with something as simple as underwear. Six pairs of these beauties? I’m set for weeks! —Liam Porter
If you want your underwear game to go from zero to hero, the Crazy Cool Mens Comfortable Fun Nylon Seamless Short Boxer 6-Pack has got you covered—literally. I love how lightweight and seamless these boxers are; it feels like I’m wearing nothing at all, but with way more style. The nylon fabric keeps things fresh and comfortable, even after a long day of running errands or lounging around. And having six pairs means I’m always stocked up on fun and comfort. These boxers are my new secret weapon! —Caleb Benson
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Why Cool Underwear For Guys Is Necessary
From my own experience, having cool underwear isn’t just about style—it’s about comfort and confidence throughout the day. When I wear underwear that feels good and looks great, I notice a huge difference in how I carry myself. It’s the foundation of my outfit, and if that base layer isn’t right, everything else feels off.
Cool underwear often means breathable fabrics and a perfect fit, which keeps me comfortable whether I’m at work, working out, or just relaxing. It prevents irritation and keeps me feeling fresh, which is essential for staying focused and confident. Plus, knowing that what I’m wearing underneath is stylish adds a subtle boost to my self-esteem that I didn’t expect but really appreciate.
Ultimately, cool underwear is a small detail that makes a big impact. It’s a simple way to take care of myself and feel good inside and out. That’s why I think every guy should invest in underwear that’s not only functional but also cool.
My Buying Guides on Cool Underwear For Guys
When it comes to underwear, I’ve learned that comfort and style go hand in hand. Finding cool underwear isn’t just about looking good; it’s about feeling great all day long. Here’s what I focus on when choosing the perfect pair.
1. Choosing the Right Fabric
For me, the fabric is the most important factor. I prefer breathable materials like cotton or bamboo because they keep things fresh and prevent irritation. If I’m working out or on a hot day, moisture-wicking fabrics like modal or microfiber are my go-to to stay dry and comfortable.
2. Style and Fit Matter
I’ve tried boxers, briefs, boxer briefs, and trunks. Each has its own vibe, but I find trunks and boxer briefs offer the best balance of support and style. A snug fit without being too tight is key—I want underwear that moves with me, not against me.
3. Consider the Waistband
The waistband can make or break comfort. I look for soft, flexible waistbands that don’t dig into my skin or leave marks. A good quality waistband also lasts longer without losing its elasticity, which is a bonus.
4. Breathability and Ventilation**
Cool underwear should keep things airy. I look for designs with mesh panels or breathable fabrics that enhance airflow. This is especially important during workouts or warm weather.
5. Durability and Care**
Since I wear underwear every day, I want pairs that can handle frequent washing without losing shape or color. Checking care instructions and reviews about durability helps me pick long-lasting options.
6. Fun and Unique Designs**
Cool underwear doesn’t have to be plain. I like to add a bit of personality with fun patterns, bold colors, or subtle details that make my underwear stand out — even if only I see them!
7. Price vs. Quality Balance**
I’ve found that spending a little more on quality underwear pays off in comfort and longevity. However, there are plenty of affordable brands that offer great value. I always compare and read reviews before making a choice.
Final Thoughts
Cool underwear for guys is really about combining comfort, style, and practicality. When I keep these factors in mind, I always find pairs that keep me feeling confident and comfortable all day long. Hopefully, my tips help you discover your own favorites!
Author Profile
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Marvin Ensor is the creator and main reviewer behind WayZada, where curiosity meets honest consumer insight. With a background in industrial design and hands-on experience in product development, Marvin brings both technical understanding and real-world testing to every review. Before starting the site, he worked with outdoor gear and small electronics companies, helping shape products from prototype to shelf. That experience sharpened his eye for detail and gave him a genuine respect for products that actually deliver on their promises.
In 2025, Marvin turned that passion into Wayzada a space built to help readers make smarter, better-informed buying decisions. Living just outside a mid-sized U.S. city with his partner and rescue dog, he spends his weekends testing new gadgets, exploring trails, or fine-tuning reviews in his workshop. His writing focuses on clarity, transparency, and usefulness so readers can trust they’re getting advice rooted in experience, not marketing hype.
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