12 Most Comfortable Underwears for Men in 2018

Once upon a time the most comfortable men’s underwear were made from simple cotton and came in a few basic forms. Those would be the classic brief and the boxer short although we would be remiss if we did not mention the good old Long Johns. Sure, there have always been exotic styles across the decades, but they most are far from what consumers would consider mainstream.

When it comes to comfort, things can be tricky as it is going to depend on your style, preference, and your overall build. What some may men may find comfortable, others will not, which means we are going to look at several types of the most comfortable underwear for men. The key word being comfort, so there will be no G-Strings on this list.

You are not going to find any “multipack” deals either as we are shooting for comfort, not cheap bargain briefs. They don not sell designer jeans or sweaters in packs of 3, so we are only focusing on underwear that comes in per pack. While they tend to be more expensive, you get what you pay for, and nobody wants holey drawers after a few washings.

With that in mind let’s take a look at our top 12 which consist of a solid mix of Boxers, Briefs, Trunks, and the slim fitting Boxer Brief.

Top 12 Comfortable Underwears for Men Table

DesignNameOpen or Closed FlyMain MaterialRating (1-5)
  1. Calvin Klein Men’s Athletic Boxer Brief Closed Nylon 4.8
  2. Calvin Klein Men’s Iron Strength Micro Low Rise Trunk Closed Nylon 4.7
  3. Perry Ellis Men’s Luxe Solid Boxer Open Nylon 4.6
  4. Calvin Klein Men’s Underwear Steel Micro Briefs Closed Nylon 4.6
  5. Texere Men’s Bamboo Jersey Underwear Boxers Open Bamboo 4.6
6. Emporio Armani Men’s Cotton Stretch Trunk Closed Cotton 4.6
7. Saxx Mens Kinetic Boxer Briefs Closed Nylon 4.6
8. Jockey Men’s Underwear Knit Boxer Open Cotton 4.5
  9. ExOfficio Men’s Give-N-Go Brief Flap Nylon 4.5
  10. Saxx Men’s Vibe Modern Fit Boxer Closed Viscose 4.5
  11. Calvin Klein Men’s Iron Strength Micro Hip BriefClosed Nylon 4.5
  12. ExOfficio Men’s Give-N-Go Boxer Brief Flap Nylon 4.4

Men’s Underwear Buying Tips

While comfort can be a “state of mind” in some cases, your underwear is not one of them. Unless you want to be uncomfortable throughout the day, keep these tips in mind.


It goes without saying that if you want to be comfortable down there throughout the day. Things can become cinched or pinched with a bad pair of drawers which can quickly put a frown on your face.

We won’t delve too much into adjusting but will say you do not want to be “that guy” who constantly finds himself digging at their crotch to adjust. It is not a good look for anyone, especially in public or family functions. Do not be that guy.

While the materials used and the fly do play an important part, you will consider what you like and what feels good first. The most comfortable underwear in the world is essentially worthless if it bunches up in the wrong place or is loose. The latter can be an issue with boxer briefs depending on the material.

The waistband is also something to consider depending on your build and the style of drawers you have set your sights on. Keep your waistline in mind unless you want the red band of shame.

The Fly  

There are really just two types of underwear flies these days with the “open” fly and “closed or sealed” fly.

  • As the name implies, a closed-fly is sealed and has no opening in the front; this means you will have to pull them down when nature calls as there is no flap in the front; this is common on boxer briefs, trunks and other form fitting types of underwear. Some will have a vent, but more often than not, closed means closed.
  • Open-fly underwear are generally boxer shorts and use buttons in the front. Some of the sassier models have zippers or other types of exotic enclosures, but that is not a road most of us are willing to go down.

The third option comes with the old tighty whities and has a flap or vent on one side. Normally found on briefs, this feature occasionally makes its way to boxer briefs as well.


If you appreciate underwear that keeps things nice and snug, you may want to opt for something with a higher amount of spandex. These can be work on any occasion but are perfect for sports, exercise or just folks that really prefer a close fit. How tight they get depends on the blends used but you are mainly going to be dealing with nylon and spandex with a little cotton thrown in for extra comfort.

Speaking of cotton, it is still the most comfortable fabric around but does not do so well on its own. When mixed with other material like nylon or viscose, they tend to hold up better over time. The higher the cotton percentage, the easier it is for them to become stretched over time through wear and repeated washings.

While those are the main types of materials you will find on our list, there are just a few since other exotics have come into play along with popular options like good old silk. Another thing to consider if you are an athlete or the sweaty type, there are plenty of materials that can keep you cooler down below. Some material is even hypoallergenic for those with sensitive skin.

Top 5 Most Comfortable Underwear for Men

1. Calvin Klein Athletic Boxer Brief

Fancy yourself an athlete? If so, the Athletic Boxer Brief from Calvin Klein could be just the thing for you. These are form fitting thanks to a mixture of 87% Nylon and 13% Elastane. That will give you a snug fit in all the important areas and ensures they will retain their form longer than their cotton-based brethren.

In regards to the design, CK kept things simple and classy for this particular pair of underwear. It has flatlock seams to help prevent chafing, contrast stitching and the popular Calvin Klein logo stitched around the waistband. They also have a contoured pouch for extra comfort where it counts. While classy, these are only available in Small and Medium although you can choose between Black with Grey stitching, Blue with black stitching or Orange.

2. Calvin Klein Iron Strength Low Rise Trunk

It should come as no surprise that Calvin Klein is going to be a frequent contributor to our list of the most comfortable underwear for men. That is due in part to the fact they are well-known for making underwear (you’ve seen those commercials) along with the quality construction and materials used. The Iron Strength Low Trunk almost made the top spot and is a fine option if you want something in-between a boxer and a brief.

Trunks have become quite popular over the past few years, and this is one of the more stylish options available. They will be snug with a mix of 91% Nylon and 9% Elastane but comfortable with active support and a contoured pouch up front. There is nothing too fancy about these trunks as they have a clean look that contrasts well with the company’s “Iron” waistband and large logo on the front.

As for the colors and sizes, you will have plenty of options. The Iron Strength Low Rise Trunk is available from Small to Extra Large in a whopping 19 colors. That includes old standards like Black and White along with hues like Striking Lime, Bright Nectar, and Bridge Blue just to name a few.

3. Perry Ellis Luxe Solid Boxer

Boxers have long been considered a top option when it comes to the most comfortable underwear for men. That would be because most of them are made from cotton and have a loose, comfortable fit. Well, the Perry Ellis Luxe Boxer are quite comfortable, and a lock for our list but they do buck the cotton trend. They are made from a blend of 88% Polyester and 12% Spandex but are machine washable to make things simple.

This microfiber boxer offers up a bit of stretch in the legs, waistband and fly. As for that feature, you will get buttons which make them ideal for dressy occasions when untucking your shirt can be an issue. We have all been there, and that is where classic boxers come in handy. The Luxe boxers are available in Medium, Large and XL with six different classic colors ranging from Black to Red.

4. Calvin Klein Steel Micro Briefs

If you were wondering when the classic brief would make the cut, you need wonder no more. Calvin Klein is back to complete their underwear trifecta with the Steel Micro briefs. These has a similar style to the Iron Strength line and are made from the same blend of material but cut high on the hip.

Chaffing will not be a concern with their flatlock seams which fights back against rubbing and red marks while providing an extra measure of comfort. These snug briefs range from Small to XL and are available in 13 styles including a few with thin stripes if you want something a bit different than the usual solid.

5. Texere Bamboo Jersey Luxury Boxers

Now for something different: the Texere Silk is behind this slick set of boxers that have a traditional style but are not made by traditional means. While they are sown, they are made from an exotic blend of 30% jersey cotton and 70% Bamboo Viscose. That is one combination you are unlikely to find anywhere else.

Bamboo plant matter used in clothing is said to be more hypoallergenic and odor resistant than other materials including cotton. They will keep you cool and are listed as “true to size” despite the materials used. That said, they can still be machine washed in cold water and tumble dried so no special care is needed if you follow the instructions. The Texere Bamboo Boxers are available from a Small all the way up to XXL in five different colors with Black, Heather Grey, Heather Charcoal, Heather Blue and Heather Burgandy.