12 Best Men’s Underwear That Are Comfortable & Stylish

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Finding the right pair of underwear can be a tricky endeavor for a lot of men.

You don’t want something too tight, material that isn’t breathable, nor one that just generally gets in the way of your daily life. In addition, a good pair of underwear will support your package to allow for a great presentation.

In this guide, we will be reviewing the best men’s underwear of 2021, along with sharing with you some key tips to keep in mind when making your decision.

Let’s get started:

Comparing the Best Men’s Underwear

Based on our research, we found the following men’s underwear to be among the best based on the following categories:

  • Cut / Style: While unique to every man, the right underwear should complement your natural body movement.
  • Material: Not only will this ensure that your underwear is breathable, but the right blend of materials will also keep things in place downstairs.
  • Best For: Whether you are looking for a pair to work out in, or one to keep you warm during winter, we award the following underwear for certain intents.
  • Price: We aren’t made of money, here’s a look at how much you should spend on a new pair of underwear.
  • Rating: Based on a variety of qualitative and quantitative factors, we rate the most popular men’s underwear brands.
NAMECUTMATERIALBESTRATING
Tommy John Second Skin TrunkBoxer BriefsMicro Modal, SpandexOverall5.0
Pair of Thieves Superfit Boxer BriefsBoxer BriefsPolyamide, SpandexUnderwear for Chafing4.9
Tani USA Men’s SilkCut Boxer BriefBoxer BriefsMicro Modal, SpandexUltra-Soft & Performance Fabric4.8
Mack Weldon Knit BoxersBoxerCotton, Modal, SpandexComfort4.8
Calvin Klein 100% Cotton Classic Boxer BriefsBoxer BriefsCotton100% Cotton Underwear for Men4.6
Tommy John Second Skin BriefBriefsMicro Modal, SpandexFitted Underwear for Men4.6
Minus33 706 Kancamagus Merino Wool Men’s Thermal UnderwearFull LegWoolThermal Underwear4.6
Saxx Quest Boxer BriefBoxer BriefsNylonFor Ball Support4.5
Adidas Sport Performance Boxer BriefsBoxer BriefsPolyester, SpandexWorkout Underwear4.5
ColdPruf Dual Layer BottomFull LegPolyesterLong Underwear for Men4.4
2(X)IST Essential Cotton ThongThongCottonSweaty Balls4.3
Hanes Comfortsoft 100% Cotton BoxersBoxersCottonCheap Underwear4.2

4 Tips for Buying Good Underwear

When deciding on a new pair of underwear, keep the following in mind:

1. Style

Men’s underwear can come in a few different styles; here’s a quick look at each::

  • Brief: These are short and keep things snug around the crotch area. Typically relying on an elastic waistband and a y-shaped fly, briefs won’t bunch up, making it pretty comfortable.
  • Boxer Shorts: Fair bit looser than the standard brief; they have a cool and airy feel. The fly will either be folded fabric or a button.  While perfectly fine for daily wear, boxer shorts are also great for sleeping.
  • Boxer Briefs: A modification of the boxer short, stylish boxer briefs are made of a similar cut but are form-fitting. Great for both performance and daily underwear as they prevent chafing.  Fly will either have access or be sewn shut.
  • Trunks: Similar in both fit and feel as boxer briefs, trunks are cut slightly higher for better movement range.
  • Niche Styles: Beyond the few styles above, some novelty underwear men may wear include thongs and silk boxers.

2. Body Type

Men’s bodies come in many different shapes and sizes. However, the same cannot be said for underwear. To find a pair that fits best for you, here are a few quick tips:

  • Large Thighs: Briefs have large leg openings that allow for a greater range of motion. In addition, this higher-cut of underwear won’t bunch around your crotch when walking.
  • Thin Thighs: Trunks are recommended underwear for men with thin or slender legs. The natural elasticity within this underwear type will ensure that the fabric remains close to your skin to prevent bunching.
  • Long Legs: Boxer briefs extend slightly longer than the trunk, making them well-suited for taller men.
  • Average: Most underwear has been designed for men of this body type. You should be able to safely go with any of the underwear reviewed within this guide.

3. Waistband

When deciding on the waistband, there are two things you want to keep in mind, the height and design:

  • Height: Too high of a waistband, and it is susceptible to rolling over. On the other hand, too short, then the waistband can pinch or dig in and become uncomfortable.  Look for a moderate height here.
  • Design: Logos on the waistband are a personal choice. Do you mind if others notice, or would you rather be discrete?  You’ll find plenty of options in both categories here.  Go logo-free if you are unsure.

4. Additional Extras

Some brands may offer a few extra features.  Here are a few that may be worth checking out:

  • Moisture Wicking: With the ability to pull moisture away from your skin, you will reduce chaffing while also limiting bacterial growth, which causes odor.
  • Temperature Regulating: Unlike underwear that wicks moisture, temperature regulating underwear is sewn differently to increase ventilation. You will often find blended fabrics like bamboo that help promote greater airflow.  This can help with both odor control and virility.
  • Contour Pouch: A welcomed addition for well-endowed men, a contour pouch provides instant relief and space for your manhood.
  • Flat Seams: By reversing the seams, the smooth part rest against your skin, making the underwear feel more comfortable.

The Best Men’s Underwear of 2021 Reviewed

1. Tommy John Second Skin Trunk

Key Facts

  • Micro modal and spandex blend
  • Horizontal fly is easy to access
  • Waistband won’t roll or pinch

Best For…

Any man that wants both the softness and support from a premium brand.

Summary

A pioneer in modern underwear, Tommy John sets the gold standard with the Second Skin Trunk. Crafted from a modal fabric (90%) and a touch of spandex (10%), this pair of underwear will feel soft and wear incredibly well. Also, unlike other underwear reviewed, the modal fabric will not pill – which means that they won’t be covered in lint balls after a few washes.

One of the biggest features of these undies has to be the quick draw pouch. Unlike so many other underwears that have sewn seams in the crotch, held together by a button, or even worse, lets everything just fly out with an open slot, Tommy John has a horizontal fly that allows for easy access when needed.

Men of all sizes also like the waistband as it will stay put throughout the day. So, whether you work at a construction site or an office, you don’t have to worry about readjusting or pulling up your underwear.

Unlike so many other underwear brands, the sizes that Tommy John makes for this pair are impressive. Made for men with waist sizes anywhere between 28″ and 46″ – you should have no problem sliding into a pair of these.

Pros

  • Made from quality materials that should last for a long time
  • The best you can get out of modern underwear
  • Works for men of all professions

Cons

  • A bit pricey 

What You Need To Know

While the price may be a bit high for some, once you slide these trunks on, you will love the comfort and quickly want to replace all of the underwear in your drawer. It doesn’t get much better than this.

2. Pair of Thieves Superfit Boxer Briefs

Source: pairofthieves.com

Key Facts

  • 4-way stretch fabric
  • Anti-chafing seams
  • Moisture-wicking and breathable

Best For…

Moisture control and 4-way fabric make it the best men’s underwear to prevent chafing.

Summary

There is no denying the amount of discomfort that chafing causes. The repeated rubbing between the fabric and your skin (or skin-to-skin contact) is something that every man tries their best to avoid. Whether you live in a hot and humid climate or find that areas of your skin are prone to chafing, you may want to switch up your underwear – enter Pair of Thieves Superfit Boxer Briefs.

Designed with anti-chafing seams through flat-stitching along with a cooling mesh, these boxer briefs are highly breathable and moisture-wicking. With this intense focus on cooling and moisture control, you can feel confident that once you slide these undies on, you will instantly notice the huge upgrade.

Beyond chafing, the fly on these boxers does open up for easy access. Furthermore, the waistband has a soft lining that will feel great against your hips as it won’t pinch, dig, or roll down your side.

Backed by a SWASS (Swamp Ass) guarantee – these boxers can be refunded (first item only) 90 days after purchase.

We weren’t alone in our review of Pair of Thieves either; other men have stated that this underwear was “so fresh and cool” and that they were “super-soft,” making this simply one the best boxer briefs available.

Pros

  • Rightly priced
  • Great for someone looking for a lightweight underwear
  • Feedback from other men overwhelmingly positive

Cons

  • Not available as a multipack (for price savings in bulk)

What You Need To Know

If chafing is a constant problem for you, you should give these boxer briefs from Pair of Thieves a try. They are focused on moisture control which will keep the boys downstairs happy.

3. Tani USA Men’s SilkCut Boxer Brief

Key Facts

  • Made from a blend of modal (94%) and spandex (6%)
  • Very soft and stretchy material
  • Available in 4 colors

Best For…

Guys looking for an ultra-soft and flexible fabric in their boxer briefs.

Summary

Made from a proprietary Micro Modal Air fabric, these super soft silk-like boxers from Tani will feel great along the surface of your skin. Able to grip the contours of your body effortlessly given the high composition of spandex, guys of all body types loved the fit of these boxers. To further add to their comfort, the stretchy fit of these boxers will stay put throughout the day, so you won’t have to worry about any sort of bunching.

One unique property that many guys enjoyed about the Micro Modal Air fabric was that it was extremely lightweight, breathable, and moisture-wicking, which will keep you much cooler and more comfortable than other heavier materials.

Claimed to be softer and more durable than traditional silk underwear, these boxers will feel like a dream when pulled on. Another feature we loved about these boxers was their care instructions – machine wash and tumble dry low.

While there is some debate about the steep price commanded for these, generally, men were pretty pleased with the results.

Pros

  • Softer than silk yet more durable
  • Resists bunching up along the leg when walking
  • Made from natural materials

Cons

  • A bit pricey for underwear

What You Need To Know

These super soft boxers from Tani USA are a game-changer. Bridging the gap between luxury and daily use, they will feel great once you slide them on.

4. Calvin Klein 100% Cotton Classic Boxer Briefs

Key Facts

  • Calvin Klein is one of the most popular underwear brands for men
  • Made from 100% cotton
  • Available in many different colors

Best For…

Men who want a trusted and classic underwear brand that has set the trend.

Summary

There is no denying the amount of clout that Calvin Klein has over the undergarment industry. Introducing a pair of boxer shorts back in the 1980s (source), they set the world ablaze. Decades later, they stay true to their underwear heritage with the Calvin Klein Classic Boxer Briefs. Made from 100% cotton, these underwear offer terrific airflow while also feeling intensely comfortable on your skin.

The larger leg openings make them also a great pair of cotton boxer briefs for average to larger men. Available in various colors and sizes (SM to XL), men should have no problem finding the perfect pair to meet their unique style. While these are by no means intended to act as a base layer for gym shorts, they are much better suited as a daily driver.

Lastly the price, these Calvin Klein boxer briefs are available as multipacks, making them much more accessible for men who want to take a step up from some of the traditional mass-produced brands. With a price tag south of $30 for 3 – they are affordable for many.

Pros

  • A classic pair of boxer briefs from Calvin Klein that will likely never go out of style
  • Cotton helps to improve circulation and comfort
  • Pairs perfectly with jeans

Cons

  • Not the best to wear during workouts 

What You Need To Know

There is no arguing that these Calvin Klein boxer briefs shouldn’t be a staple in your wardrobe. They are both popular and classic, thanks to their comfortable and timeless design.

5. Minus33 706 Kancamagus Merino Wool Men’s Thermal Underwear

Key Facts

  • Made from 100% wool
  • Available in sizes XS to 6XL
  • UPF protection

Best For…

Men who want the ultimate in warmth during the frigid winter months.

Summary

When it comes to finding the best thermal underwear for men, the Minus33 706 Kancamagus Merino Wool Midweight Bottom Thermal Underwear was a standout performer.

One of the biggest selling points to this underwear compared to all other thermal underwear was its material composition. Merino wool is finding itself into all sorts of clothing for men today. This naturally and humanely sourced fabric (sourced from sheep) is a good insulator and highly breathable. While this may seem like an oxymoron, this unique fabric helps the Minus33 Thermal Underwear to regulate your temperature like no other fabric. Furthermore, if you start to do any sort of athletic activity or simply a light jog, the wool will draw moisture away from your skin to keep you dry.

Furthermore, these underwear rely on flatlock stitching that lies flat on the skin. This will result in reduced chafing in your sensitive areas with prolonged use.

With one of the largest size ranges available of any underwear reviewed, you can find the Minus33 706 Kancamagus Midweight Bottoms in sizes from XS to 6XL. Furthermore, tall men can rejoice as they also make their underwear in tall sizes.

Based out of New Hampshire (source), Minus33 supports various organizations and offers a one-year warranty along with a 30-day satisfaction guarantee on all of their products. Therefore, if you are slightly skittish about trying a new brand, this USA-based company stands by its product.

Pros

  • Made from a super comfortable wool
  • Naturally anti-microbial material
  • Acts as an effective base layer for winter

Cons

  • A bit expensive
  • Best for only winter use 

What You Need To Know

If you are tired of being cold and looking for an underwear option that will keep you warm, it doesn’t get much better than with the Minus33 706 Kancamagus Merino Wool Thermal Underwear.

6. Adidas Sport Performance Boxer Briefs

Key Facts

  • Synthetic blend wicks moisture
  • Dries quickly when drenched with sweat
  • Won’t bunch or ride up on legs

Best For…

Men looking for the best boxers that won’t get in the way when breaking a sweat.

Summary

When it comes to athletic-focused underwear, there is no beating the Adidas Sport Performance Boxer Briefs. While normally boxer briefs aren’t recommended for intense running, this pair from Adidas is an exception. With large leg openings and a trunk-like cut, the fully synthetic blend (91% polyester, 9% spandex) boxer briefs will do a great job at wicking moisture while keeping your manhood comfortably in place.

With a wide waistband, this underwear will never require readjustment when the going gets tough – nor will they dig into your hips either.

While the specs on this athletic underwear are impressive, we also like the little details. For starters, the fly on these boxer briefs is sewn shut for added security. Given that these aren’t intended for daily wear, most men will welcome this addition. Furthermore, the fabric is also double-lined in key places to ensure additional comfort and support.

If you hit the weights regularly and want to go with a trusted performance brand, then these short-cut boxer briefs by Adidas will be your best pick.

Pros

  • Designed for athletic support
  • The waistband will be comfortable
  • Attention to detail is unmatched

Cons

  • Not daily underwear (and that’s okay)

What You Need To Know

These are undoubtedly the best athletic underwear for men. It hits all the right marks when it comes to shape, stretch, and materials. Expect to focus on your athletic performance rather than having to readjust your underwear every few minutes like other brands. 

7. ColdPruf Dual Layer Bottom

Key Facts

  • Made from synthetic materials
  • Incredibly affordable
  • Mid-rise provides comfort

Best For…

Men who want an alternative to long johns that are also affordable.

Summary

Whether you are going out on a camping trip or are looking for a pair of long underwear to wear beneath your jeans when the temperatures begin to drop, the ColdPruf Long Underwear is a perfect pick.

Unlike other product reviews that feature cutting-edge technology, these simple underwear rely on a moisture-wicking 100% polyester blend. What does this mean for you? It means that your precious body heat will stay in while the moisture that causes chafing will be drawn away. Therefore, you can feel both comfortable and warmer all winter long. With a sub $20 price point, these can easily work into just about any man’s budget as well.

Based out of North Carolina, ColdPruf is a subsidiary of the Indera Mills Company – a textile maker that makes various camos and performance wear.

For those men who like to ‘vote with their wallet,’ you will be happy to learn that ColdPruf has a few green initiatives that they take part in listed on their site.

Pros

  • A simple pair of long underwear that will keep you warm
  • Environmentally conscious company
  • Comfortable to wear for extended periods
  • A rich history in textile manufacturing

Cons

  • The ankle may be a bit tight for some
  • Limited styles

What You Need To Know

For men looking for a pair of inexpensive long underwear that can keep you warm during the winter, this is your best choice. The ColdPruf Dual Layer Bottom is a comfortable and budget-friendly pick.

8. Tommy John Second Skin Brief

Key Facts

  • High-cut perfect for men with large legs
  • The smooth fabric feels great on the skin
  • Contour pouch good for endowed men

Best For…

Men who have larger legs or are looking for a bit more room if they are well-endowed.

Summary

While they often get made fun of for being tighty whities or the underwear your dad wears, there is no denying their comfort. With a higher cut around the upper thigh, you never have to worry about bunching or pulling of fabric as you do with a standard pair of boxers. Furthermore, the unique cut of briefs allows those men who have a larger package to have some increased comfort thanks to a larger pouch.

Style aside, as is true with other Tommy John underwear, these briefs rely on that same silk-like fabric that will feel great against your skin.

Currently available in 10 different colors and patterns that span both neutral to bold, you can have some fun picking out a pair that works with your unique and fun style.

Like the other underwear we reviewed, these briefs have a horizontal fly for easy access.

Pros

  • Plenty of room for your junk
  • The high cut won’t bunch around your man parts
  • Will fit great for average to larger men
  • Won’t get a wedgie

Cons

  •  Pricey for a brief

What You Need To Know

If you are looking for a streamlined appearance and a pair of underwear that will stay firmly around your waistline without being uncomfortable, then these briefs by Tommy John are a solid pick. While carrying a luxury price point, once worn, you will never want to go back to the basic brands.

9. Saxx Quest Boxer Brief

Key Facts

  • Ballpark pouch provides support from the sides
  • Works for many different activities
  • Available in 14 different colors

Best For…

If you sweat quite a bit, this hybrid performance underwear will work to wick moisture while providing support to your genitals.

Summary

When you look at any performance shirt made from large brands, they are never made from cotton. Instead, they are typically made from a blend of synthetic materials. The reason for this reliance on artificial fibers isn’t just due to their increased durability, but these fibers are also great at drawing sweat away from the skin. Evident in these sweat-wicking boxer briefs by Saxx, they are designed to “combat clamminess” by relying on a unique blend of nylon (77%), spandex (14%), and polyester (9%). Not only will this blend reduce moisture on the skin, but it is incredibly lightweight and highly breathable.

As great as this fabric may be, what sets these Saxx Boxer Briefs apart from other brands is their design. When sliding these briefs on, you will notice that they have a flat stitched seam and bonded back rear tag for maximum comfort. But it gets better. Saxx developed a proprietary “Ballpark Pouch” that keeps your manhood and testicles from shifting around too much. While not as tight as old-school jockstraps, this extra soft side webbing will provide some structure in moments that matter.

Currently available in 14 different colors and patterns, you can find the perfect pair to match your style and personality.

Pros

  • Sweat-wicking fabric keeps the moisture away
  • Anti-odor fabric combats bacteria buildup
  • The pouch provides movement security for your genitals

Cons

  •  Some reviewers found bunching on the legs

What You Need To Know

If you hate your nuts feeling sweaty, the Ballpark Pouch on these Saxx undies will ensure they stay nice and cool. When you couple that with the anti-odor fiber and fabric that carries little weight, then you have the best men’s underwear for ball support. 

10. Mack Weldon 18-Hour Knit Boxer

Key Facts

  • Fabric air-dried for 18 hours before stitching
  • Covered waistband
  • Large gusset for comfort

Best For…

Men who want a pair of underwear that feels supremely comfortable.

Summary

When reviewing this underwear, you will see that Mack Weldon prioritized comfort over everything else. Crafted from a hybrid blend of fabric that contains cotton (47.5%), modal (47.5%), and spandex (5%), you have underwear that strikes the right balance between being super soft and a touch form-fitting. While the fabric is stellar, it’s the little things that count. First, the pouch is stretched, providing a great area for your manhood to not feel too cramped throughout the day. Secondly, unlike most other underwear brands, Mack Weldon smartly covered the waistband in a soft fabric. Therefore, it will never feel like it is pinching into your hips when worn throughout the day.

When it comes to intent, these trunks are best worn for daily use or nightwear. Given that the fabric is not as form-fitting as other brands reviewed, there may be some bunching that occurs if you try to wear these when working out.

Available in solid colors and prints, you should have no problem finding one to fit your unique lifestyle. Lastly, the price on these can be a bit steep compared to the others reviewed. Therefore we would recommend waiting for sales (or simply signing up for the mailing list) before purchase if you want to save a few bucks.

Pros

  • Great for people in search of comfy underwear
  • Tailored fit
  • The large pouch doesn’t constrict

Cons

  • May experience bunching when running
  • The button fly isn’t for everyone

What You Need To Know

These are the best boxers if you are looking for a comfortable pair of underwear. Whether you plan on wearing them to work or to sleep, you may never want to take them off.

11. Hanes Comfortsoft 100% Cotton Boxers

Key Facts

  • 100% Cotton Underwear
  • Extremely affordable
  • Available in neutral colors

Best For…

Men who are on a tight budget will love the 100% cotton blend in these affordable boxers.

Summary

Hanes Men Comfortsoft Boxers is a staple boxer for a lot of men. The chances are that you have probably worn a pair once in your life. Made from 100% cotton, they are extremely cheap while also highly breathable. So many men love these boxers (aside from the price) due in large part to the airflow they provide.

Unlike some expensive men’s underwear that may pill or cause lint balls after a few washes, these boxers are fairly durable (although not as tough as some of the other activewear boxers we reviewed); they can withstand the test of time compared to most other garments.

While these boxers are good, there are some notable drawbacks. First, susceptible to bunching, given their lack of spandex in their composition, will make them quite annoying if you find yourself in any active situation. Secondly, these boxers don’t present well. Unlike others that may help to enhance the size of your member to the eye of others, these won’t help at all.

Pros

  • Provide great value for an underwear
  • Washing instructions are dead simple
  • Go-to pick for men on a tight budget

Cons

  • Runs a bit small, so may want to size up
  • Often bunches under your clothes

What You Need To Know

If your money is tight, then these boxers work. While perhaps not the top of the list, they are breathable and comfortable. Unfortunately, they are susceptible to sweat stains in hot weather – so wear accordingly.

12. 2(X)IST Essential Cotton Thong

Key Facts

  • Made from 100% Cotton
  • Easy care instructions
  • Contour pouch provides plenty of support

Best For…

Men who want adequate support with minimal fabric or movement restriction.

Summary

We are willing to bet that the 2(X)IST Essential Cotton Thong will be a stretch for a few (ok, a lot) of men reading this. Made from 100% cotton, these minimal coverage underwear are a pleasure to wear. Rather than going commando, this cotton thong provides great support thanks to the sizeable contour pouch for your manhood.

Rather than wearing briefs (boxer or standard), the airflow that you will get to your crotch will be unmatched – and probably the reason why so many that try these on will never go back to their standard underwear ever again.

As for the straps, they are incredibly soft, so while they are rather small – especially compared to the thick waistbands found in so many boxer briefs, they will never feel like they are digging into your skin after a few hours.

Whether you carry a lot or very little weight, the low-rise fit of the thong will be able to fit easily (and discretely) below the beltline – as to avoid any sort of embarrassing fashion snafus.

Pros

  • Great for many occasions
  • Lines discretely go away under your layers of clothing
  • Perfect for hot climates

Cons

  • A tough sell for many men

What You Need To Know

Once you slip on this no-frill y-back thong by 2(X)IST you will be surprised to find out just how comfortable they are.