What’s The Most Comfortable Underwear For A Guy?

Comfortable brief Underwear
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Even though nobody can see it, your underwear will set the tone of your day. 

Having a great deal of comfort can make you feel good and confident. An ill-fitting one can cause chafing and discomfort throughout the day. I’ve been there and it sucks.

So in this article, we look at what’s the most comfortable underwear for a guy. In creating this list, I considered several factors that affect comfort the most, like fit, fabric, and others. We detail why each one matters for men’s underwear. 

After that, I’ve listed the most comfortable underwear you can wear right now based on the criteria set. 

However, I understand that every guy has their own preference. You may not agree with the ranking and that’s all good. What matters is you’re comfortable with your underwear choice.

Criteria For The Most Comfortable Underwear

Your underwear should fit well and feel good on your skin. It should make you feel good about wearing it. So to find the most comfortable underwear, I considered the following aspects:


Fit comes down to your body and underwear type. You should always go for what fits just right all around. Going for a smaller size will make it tight around your waist and squeeze your package too much. Then going too big runs the risk of your underwear falling and offering no support at all.

Naturally, boxers are more loose compared to briefs, with boxer briefs being a cross of the two. So expect fit to be different depending on the underwear type. 


One underwear type can offer different functions. For example, some boxer shorts come with a fly to make it easier to pull it out when you need to pee. Some boxer briefs are designed with a pouch that gives more room for bigger packages. 

This has caused some division, with the pro-fly or pouch on one side and anti-fly on the other. 

But flys and pouches are additional functions that don’t take away anything from an underwear’s most basic function. Understandably, these add-ons matter to some guys and you may find them useful as well as comfortable. 


The fabric used is a major part of underwear comfort. How the fabric feels on your skin will give you an immediate sense of its comfort level. Even if it fits well, if it’s made with fabric that your skin disagrees with, it’s not gonna be a wonderful ride.

Cotton is the most common fabric used, which is comfortable enough for most guys. However, some brands use cotton blended with other types of fabric. 

This makes them softer than the 100% cotton variety. These cotton blends can contain polyester, linen, or rayon and result in a fabric that’s softer on the skin and feels lighter to wear.

Other fabrics used for underwear are satin, latex, spandex, Supima cotton, and more. There are also hypoallergenic fabrics for those with sensitive skin.


Closely related to fit, your underwear should be able to give you the support you need when and where it matters. Because underwear comes in different shapes and forms, its support will vary.

This affects comfort since underwear’s most basic function is to cover and support your package as you go about your daily activities.

Most Comfortable Underwear Types Ranked

Now that we have set our criteria, here are the most comfortable underwear listed from the most to the least comfortable. But take note that this isn’t a list to rule them all. You’re still free to wear whatever underwear type you find most comfortable.

Boxer Briefs

It’s no surprise that the most popular underwear type is also the most comfortable. 

Boxer briefs offer the best that briefs and boxer shorts have to offer. Made popular in the 1990s by a designer brand, they feature a mid-rise style that has complete coverage with a length that covers part of the thigh.

What makes boxer briefs the most comfortable is the support it offers without sacrificing breathability. 

This underwear covers your whole package and your butt. The form-hugging style isn’t too tight and prevents chafing, especially in the inner thigh. 

The crotch area offers an extended space where your package can rest comfortably. For guys who carry a bigger stick, a pouch in the front area can extend to accommodate your asset. 

It won’t squeeze your member like briefs tend to do and you won’t be left hanging like how boxers would.

Boxer briefs are great for daily use, especially the ones made with higher-quality fabric like Supima cotton. You can use it with a wide range of clothing, from formal wear to athleisure.  It even provides enough support and comfort for some sports or fitness activities.

They’re more breathable than your average brief. If you opt to go with moisture-wicking or quick-drying fabric, you’ll feel a lot cooler down there even when you’re sweaty. This prevents bacteria from forming and is more hygienic.


Trunks come in at a close second since they are basically the same as boxer briefs. The main difference lies in the length. Trunks are shorter than boxer briefs, with their hem just a little below the family jewels. This gives them a squarish shape.

In terms of comfort, trunks offer the same level as boxer shorts do. What makes them second best? Because trunks are shorter, there’s the possibility of chafing if you have thick thighs.

Boxer Shorts

When it comes to breathability, boxer shorts are kings. 

It’s almost like going commando but it provides cover so you won’t be totally exposed in case you’re caught with your pants down. 

However, its breathability and comfort rely on when and where you choose to wear boxer shorts. 

Boxer shorts can also come in a variety of fabrics and designs. They often have flys so you can let it out through the front gate rather than jumping over the fence, which some find more comfortable.

When worn with the right clothing and situation, you won’t get more comfortable with boxer shorts. Your junk will thank you when paired with loose-fitting pants or shorts in a hot and humid environment. 

Indoors, you can wear boxer shorts if you’re just gonna hang. 

And hang you will. Since boxer shorts offer no support, it lets your package hang loose and breathe. It’ll feel cooler and prevent moisture build-up. It can be a very refreshing feeling on hot days.

But if you wear it with the wrong pair of pants, boxers can ride up and crumple inside your pants. 

Chafing can happen when your thighs rub against each other since it’s roomier inside. And in case you get random erections throughout the day, it can be uncomfortable and awkward.

Briefs/Bikini Briefs

The OG of modern underwear, there’s a reason they’re called “Tighty Whities.” This underwear type has a tighter fit than all the underwear types ahead of it on this list. 

Meanwhile, bikini briefs are a sexier version of the standard briefs. They function the same as briefs but with lesser coverage. They often have a lower waist than briefs and have a higher cut for the legs.  

Many of us have at least one pair of briefs at home because they work. They hold everything in place and give the most support. But this is where comfort can become an issue.

You can wear briefs with anything, from skinny jeans to baggy shorts. 

You can wear them anywhere, from the office to the basketball court. But you’ll really feel it after wearing it the whole day. It can get hot and cramped down there, especially when things get hard and you don’t have enough wiggle room.

And when you’re on your butt for 8 hours at work, you’ll feel the Y-shape hem sticking to your skin every now and then. Plus, the tighter fit isn’t so good for your little swimmers as the warmer temperature can decrease sperm count.

So for briefs to be more comfortable, go for the variants with sweat-wicking properties or soft and high-quality fabric. 

This can reduce the temperature and prevent the fabric from sticking to your skin.


While the front part of the thong provides ample support and comfort, it’s the string at the back which can make it uncomfortable especially for everyday wear. It’s like having a wedgie the whole time.

First-time wearers will definitely feel that way but you can get used to it if you wear it often enough. Or maybe you won’t. 

It’s a tricky situation since a little movement here or there can misalign the fabric resting on your crack and make it uncomfortable no matter how used to it you are. 


Last are jockstraps or the athletic supporter. 

This special type of underwear is used for highly strenuous sporting activities. They provide full frontal support to lift your package upwards and away from your body to decrease temperatures during intense activities.

This underwear is meant to be tight to give you more lift. Since it’s often used for extreme or high-impact sports, it can be uncomfortable when worn for too long. 

Also, if you choose to wear another layer under or over your jockstrap, it will get hot and moist in your nether regions especially if you sweat a lot as I do. 

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