Feeling and looking good starts with the first thing you put on every day. For most people, that begins with the underwear game. Want to feel like a bum?
Throw on some faded, ratty undies with holes. Want to feel like a cool, take charge James Bond kind of man? Throw on a fresh pair of stylish, sexy underwear.
The best stylish men’s underwear is the kind you can sport with supreme confidence. Want to be a boss with swag? Get the right underwear in the perfect cut, color, and style that’s also comfortable.
Getting the perfect style of undie is the trick. Boxers offer zero support and have lots of extra fabric. Briefs don’t have that problem, but they get a bum wrap especially from the ladies who prefer to see their men in something that doesn’t remind them of panties.
The compromise would be to go with a boxer brief. The downside is that they might ride up a tad requiring a little bit of an adjustment. But if the boxer brief hooked up with the brief, the resulting love child would be the trunk which makes a great everyday underwear option.
If you’re searching for underwear that will fit your body and lifestyle while serving up some piping hot sex appeal, this article is for you. Before diving into the best stylish men’s underwear, here are some features you’ll need to consider so you can level up your undy game.
Stylish Men’s Underwear Comparison
Here's a quick comparison of all the underwear we looked at when putting together this guide. You can read full reviews of each below.
Product
Rating
Material
Price
Top 10 Best Stylish Men’s Underwear
Pro: Flat stitching.
Con: Ride up.
Super comfortable: Calvin Klein’s microfiber boxer briefs are a reminder that feeling good and looking sexy in nice underwear isn't just for ladies. The design makes many a booty look good. Speaking of the love below region, this boxer brief keeps the boys from feeling crowded or uncomfortable.
Crotch support keeps you comfortable when sitting, standing, or walking. This supportive underwear is super soft and beyond comfortable. It holds everything in without being too tight or loose.
The briefs fit as expected and don’t ride or bunch up. Sizes run from small to x-large. Smooth, flat stitching prevents bulkiness.
The 89% nylon will help you stay cool. The material is very soft and stretchy. This durable underwear stands up to multiple washes and maintains color, elasticity, and form.
The downside is that these aren’t tagless. Fix this issue by cutting the tags out if it causes discomfort.
Pro: Great fit.
Con: Thin material.
Supportive: Tommy Hilfiger created undies that are perfect for the modern man who likes to wear his jeans on the slimmer side. This underwear lacks a big pouch and holds the man bits very well.
Now that pants are getting tighter, men need well-constructed drawers that will help hold back the merchandise. This brief does just that without crunching the cashews.
The boys will be in heaven. Sizes range from small to xx-large and come four in a pack. The 100% cotton fabric is durable, comfortable, and breathable. Also, the fit is great.
It isn’t loose, bulky, or too tight. On the flip side, if you have a bubble butt, this underwear may ride up and give you problems. Keep this from being an issue by going up a size.
Pro: Moisture Wicking.
Con: Skintight.
Smooth, breathable fabric: Puma got it right with this perfect blend of 85% polyester and 15% spandex. The fabric is smooth and feels soft against the skin. It breathes well which makes excess sweating a nonexistent factor.
Also, they dry quickly allowing you to stay cool and comfortable as you go about your day. This boxer brief has strong, well-made seams that keep the underwear in place. The design is form-fitting, especially around the legs.
The construction is superb. Another perk is that there’s no chafing. Feel free to enjoy a day of soccer, hiking, or running with this comfortable boxer brief.
The downside is that the threading at the seams is a bit thin so a rip can happen easily. Buy a backup pair in case one set gets ripped.
Pro: Great color selection.
Con: Leg openings a little tight.
Sexy: Nudus’ boxer briefs are well made and provide all-day comfort. The 95% cotton is soft and breathable. The high-quality silk in the waistband gives you a smooth, luxe feel.
The quality is excellent. Sizes range from small to x-large. This boxer brief is beautifully sewn with no raised seams that cut or bind. It’s soft and stretchy. The underwear has been designed to hug the john and backside without feeling too constrictive.
This sexy underwear definitely holds the jingles in order. Nudu’s boxer brief even holds up well after washing and drying. This set of underwear is sure to please.
The downside is that it may run small for some men. Resolve this issue easily by going up a size.
Pro: Natural fabric.
Con: Tight waistband.
No ride up: Hugo Boss’ trunks provide incredible support and feel amazing. The 95% cotton fabric is very soft. The elastic is comfortable.
This great fitting trunk comes in sizes small to xx-large and you get 3 per pack. The support your frank and beans get is top-notch. Plus, this set of drawers doesn’t shrink after you wash them.
Another bonus is that your skin will breathe in the natural cotton fabric which will help you feel comfy and cool. On the flip side, this underwear can bring out the itch factor. Make sure you wash them first to remedy this problem.
Pro: Big man friendly.
Con: High waisted.
3D front pouch design: This boxer brief fits perfectly and provides great support for all everyday activities from welding to running races. Your goodies will stay in place the entire time. Sizes range from x-small to xx-large and come 7 per pack.
A stretchy waistband ensures the boxer brief won’t ride up or roll down. The 3D front pouch design provides more room for your man bits. Plus, it will decrease the friction between your private area and underwear.
Long gone are those days of feeling sweaty and sticky. This very comfortable and breathable underwear fits well even on tall men with long legs. Another bonus is the vibrant colors that provide a nice change from the black and gray neutrals out there.
The downside is that there’s too much fabric in the front. But all you have to do is pull the front up a little to get the support you need.
Pro: Cooling properties.
Con: High pouch.
Stylish waistband colors: Sheath’s sexy boxer briefs may have you saying that you can’t go back to any other underwear. This bad boy is made of modal and spandex to cool your nether region. The design separates the royal jewels from the scepter which reduces groin sweat and maximizes comfort.
Men who are active or work outside will appreciate that feature. Sizes range from small to xxx-large. The design provides support while also giving freedom of movement.
The material is super soft and hugs the body well. Another benefit is a non-irritating, chafe-free, tagless design. Plus, the no ride-up design keeps your nether region happy.
The downside is that the design doesn’t prevent shifting when you change positions. To avoid discomfort, don’t wear this boxer brief when doing activities that require a lot of moving. Save this undy for those chill days when you don’t plan on moving around much.
Pro: Great quality.
Con: Legs slide up a little.
Very soft: David Archy delivered a sleek, moisture-wicking trunk that’s ultra-soft and comfortable. Unlike some brands, it didn’t sacrifice function for style. Sizes run from small to 2x-large.
It’s not easy finding comfortable, great-looking underwear that has both a pouch and a front fly, but this one has both. The bamboo fabric is breathable and the u-pouch design provides more space for your twigs and berries.
In addition to helping your man parts breathe, they make the whole package look great - from the boys to the booty. The design doesn’t constrain or create unwanted wedgies in the middle of the trunk so forget about those embarrassing moments of self-adjustment.
This silky trunk feels cool and is durable. Try not feeling fancy with this undy on. On the other hand, the waistband can run small. Remedy this issue by going up a size.
Pro: Perfect fit.
Con: Not tagless.
Retains shape: Eyushijia’s bamboo boxer briefs bring a lot to the table. They’re comfortable, durable, and fit incredibly well. Sizes run small to xx-large and come four per pack.
This underwear doesn’t ride up. Plus, this brief makes the junk in the trunk look amazing.
This dapper gem is sexy, silky smooth, and comes in great color combinations. The fabric is as soft as a kitten's belly. Plus, the wide comfortable band helps it stay put as you move throughout the day.
Overall, the fit is not too tight or too loose. It’s body-hugging in the best way. This is the kind of underwear you can rock every day and even workout in because it won’t bunch as you move.
It’s tight enough to hug without constricting your jungle book. This lightweight boxer brief is so comfy you might just forget you’re wearing them.
On the flip side, some reviewers found that although the waistband follows the sizing chart in inches the rest of the underwear feels a bit tight. Keep this from being a problem by going up one size for a better fit.
Pro: Cool designs.
Con: Runs small.
Flexible material: Danny Miami’s boxer briefs are designed to catch the eye. Bright colors along with rich and elegant designs make this one of the more stylish options on the market. This undy has more to offer than a striking design.
This tagless cutie has a quick-dry moisture transport system that will keep you cool and comfortable for hours. The support stitching combined with the polyester/spandex material helps provide a snug fit so your crown jewels stay in place. Sizes range from 26-36.
The super-soft, breathable material glides effortlessly across the skin making you feel buck naked. You’ll feel as good as you look in this sexy, sleek underwear.
On the other hand, this undie is made of polyester, a synthetic fabric, which doesn’t allow for great breathability. Keep your man bits healthy by rotating this underwear out with cotton ones.
Most Stylish Men’s Underwear Buying Guide
This guide lists the most comfortable and stylish men’s underwear in a variety of cuts, colors, and designs. Besides keeping in mind the practical side of underwear selection, you’ll want to pay attention to the fit and style of your undy. These are the points to bear in mind before you start your shopping expedition.
Most Comfortable Stylish Men's Underwear
The perfect pair of underwear will be agreeable to the man bits and pleasing to the eye. But finding comfortable drawers that make you feel like a walking god of desire isn’t always easy. Regardless of the style chosen, the most comfortable drawers will have a few things in common.
The material will be of high quality. Natural fabrics like cotton and bamboo are best for comfort. Plus, they bring breathability and durability to the table. Also, opt for lightweight underwear that doesn’t bunch or ride up.
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Most Stylish Men's Underwear
If you want to trade your bland black, grey, and white drawers from some eye-catching underwear then it’s time to expand your horizons. Men’s underwear comes in a variety of striking colors and designs. A tagless, quick-dry option will keep you cool in more than one way.
Best Fitting Stylish Men's Underwear
How important is fit? It’s life-altering. In the words of the late Johnnie Cochran, “If it doesn’t fit, you must acquit.” O.J. Simpson’s attorney knew the importance of a perfect fit and so should you.
A great fitting pair of drawers will elevate your style game. As to whether it will help you beat a case, that depends on the skill of your trial lawyer. Hopefully, you'll never need one.
The perfect undy will be snug, but not too tight - walnut crackers aren’t welcome. Crotch support that keeps your boys happy while sitting or working out is a must. Supportive undies in microfiber will give plenty of stretch without compromising the shape of the underwear.
- Steel microfiber underwear boxer briefs
- Wide logo waistband and smooth, soft, comfortable metallic micro fabrication
- Tagless for comfort
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