10 of the Most Comfortable Men’s Boxer Shorts

The number one priority when choosing a great pair of boxer shorts is finding styles that are comfortable. Comfort means different things to different men when it comes to underwear. Some find the tight fit of a brief to be the most pleasant to wear. While others feel that the looser fit of a boxer style with more freedom of movement is where true comfort lies. If you are part of the latter group, we have come up with some of the best styles around, whether you are looking for looser fitting, cooler option for a hot day or you are one of the many men who wear boxers for sleeping. We have found designs in all kinds of colors, styles, fits and materials that will keep you feeling great all day or all night, whatever the case may be.

Read More: 8 Super Comfortable Men’s Pajamas

Polo Ralph Lauren Classic Cotton Knit Boxer 3-Pack

These Polo Ralph Lauren Cotton Knit Boxer set of three are a little bit more expensive than some of the other options out there, but they have a great reputation for being super comfortable and very well made. The other great thing about this design is that it has a really nice fit to it with lots of room for movement and a good length on the leg. One very important comfort feature this Polo style has is that there is no seam going up the back of the short. If you are looking for an all white  cotton boxer, this is one of the few options available. Due to the popularity of patterns and bright colors, it is surprisingly hard to get good quality, white underwear these days. This style does come with a tag that you will have to cut off.

Available from Amazon

Hanes Men’s Five-Pack Ultimate Tartan Boxers

These Hanes Ultimate Tartan Boxers are a great budget option that are made from a super soft cotton polyester blend. It has something called a ComfortFlex waistband that is supposed to be comfy and maintain its shape throughout the day, the waistband isn’t covered in cloth but that doesn’t seem to affect the comfort level.  The fabric on this short is nice and breathable, so you shouldn’t overheat in this design on a hot day.  Like most good underwear these tartan shorts are tagless, and they wash and wear very well. They come in a nice selection of tartan color combos that won’t fade in the wash. They have about a 5″ fly opening.

Available from Amazon

Tommy Hilfiger Men’s 3 Pack Cotton Classics Woven Boxers

A very popular brand for underwear are Tommy Hilfiger, in particular their 3 Pack Cotton Classics Woven Boxers style are a favorite of a lot of teens and men. These woven boxers have a covered elastic waistband with only a small logo tag at the front. They are a lightweight style that should work well under your clothes since they have a bit of structure and aren’t too loose or baggy. The material is a moderate weight, so they are breathable and should be equally comfortable in the winter and summer months.

Available from Macy’s

Jockey Men’s Underwear Tapered Boxer

Another boxer style that can be hard to find is a more tapered fit, since a lot of the classic styles are designed to be quite loose. One tapered option is the Jockey Men’s Underwear Tapered Boxer. They are a cotton/polyester blend that have a more snug fit than other types of boxers. They also have an interesting cut on the leg, so the outside is higher than the inside. The elastic waist band is relatively relaxed, so it shouldn’t make marks on your skin. If you are looking for a tight elastic this is not the short for you. The tapered style is a good if you are looking to have less bulk under your pants, and they also won’t move around as much as looser styles. This is definitely a design that you should consider if you love boxers and like to wear the slimmer leg pants, since they are much less bulky than regular styles.

Available from Amazon

Under Armour Men’s The Original Boxer Shorts

A lot of men really love Under Armour underwear, especially their boxer briefs. UA also have other styles including The Original Boxer Shorts, these are a kind of interesting design as they have some features that aren’t super common on other brands including having high-tech HeatGear sweat wicking fabric that will keep you cool. There are a lot of underwear that use sweat wicking material, but it is more popular on designs that are usually worn for working out. As a result of the fabric this UA style are super breathable and will keep you nice and cool, even in hot humid weather. As far as comfort, many reviewers report that they feel as though you have nothing on because they are so light and airy. The downside to these UA underwear is that they aren’t tagless and they are kind of pricey.  The tag is supposed to be removed before being worn, but if you aren’t careful when removing the tag it can cause some issues with the stitching.

Available from Under Armour

Calvin Klein Men’s Three-Pack Cotton Knit Boxer


Calvin Klein are well known for their tight-fitting briefs and boxer brief underwear. They only have a few boxer short styles available, but the ones that they sell are quite good as far as comfort goes. One of the CK options is the 3-Pack of Cotton Boxers that are made from a knitted cotton. These are great for sleeping in due to the extreme softness of the fabric and the really nice stretchy waistband. The fit is somewhat loose and the leg opening is a little wide if you were thinking of this style for wearing under pants, although it does seem to work well for some men especially those who have larger, more muscular thighs. This is another style that come in white, as well as lots of other colors.

Available from Bloomingdales

NORDSTROM MEN’S SHOP 3-Pack Supima® Cotton Boxers

The Nordstrom Men’s house brand is well worth a look if you are interested in some comfort designs that are well made, not overly expensive and not too baggy. This style is made from Supima® cotton, which is a high quality cotton that is known for being both soft and durable. The design of these Nordstrom underwear is a little more fitted than some of it competitors, so they work well under most pants without any bunching or extra bulk,

Available from Nordstrom

Gildan Men’s Woven Boxer Underwear Multipack

 


The Gildan Men’s Woven Boxer Underwear Multipack are another really good, budget option that are nice quality for the price. They are light, breathable, and comfortable, and are quite a loose fit, so they may be a good option if you are looking for a style to wear as pajama bottoms. The only problem with this Gildan underwear is the fabric is a little rough to start, so you need to break them in by washing them a few times to get them to soften up and be more comfortable. They do come in some nice patterns and colors. They also feature a comfort waistband and are tagless.

Available from Amazon

TexereSilk Men’s 100% Silk Boxers Underwear

Nothing beats a nice silk for comfort, and a good silk option are the TexereSilk Men’s 100% Silk Boxers Underwear that are available on Amazon. These are definitely a style that you would wear as a sleep short, as they are quite bulky and aren’t going be a great fit under most pants. They are very luxurious and come in 8 nice color options. They are also reportedly very durable, more so than other silk underwear available. The only downside to this design is that silk needs to be hand washed or dry cleaned.

Available from Amazon

Mack Weldon Boxers

Mack Weldon are a newer underwear brand that are very popular for their boxer brief styles. They have 2 boxer options, one is woven cotton while the other is knitted cotton. The woven open is good for wearing under your clothes, while the cotton knit is a great style for sleeping.  They are both designed to be bulk free and made with a slightly stretchy fabric. Both styles don’t have a seam up the back and are instead made with a one piece back panel.

Available from Mack Weldon

What to Look for in a Boxer Short

Fly– Traditional boxers usually have a fly opening, although most men never use it. Most fly openings have either a center button or a snap closure. If you are one of the men who likes to use the fly opening, you may want to check that the opening length is the right length for you.  A long fly opening would be about 6″.

Inseam Length An inseam is the seam that runs down the inner part of your leg. It is a good indication of how long the shorts will be, and where they will fall on your leg.

Back Seam– The newer styles are getting rid of the back seam that runs up the middle part of the back. The back seam can be uncomfortable to some men. It is usually replaced with a one piece back panel that has no seam.

Leg Opening– A good feature to be aware of when shopping for underwear is the size of the leg opening, especially if you have muscular legs. It can affect your freedom of movement and also cause issues with the boxers moving around and bunching up in unpleasant ways.

Fabric– The most popular types of boxers are usually made from either a knit or a woven cotton blend. The fabric choice is pretty important to how comfy you are going to feel in your underwear. Woven fabrics are great for wearing under pants since they are able to maintain their shape and structure and lay flat under your clothes. Some woven fabrics may be a little rougher than some of the super soft knits, but that is not always the case. Knit fabrics are usually more stretchy than woven, and aren’t able to hold their structure quite as well as the woven options. Knit designs can be a good choice for sleeping, as they often feel quite luxurious.

Waistband– When choosing a waistband, you will need to know your sizing (you have to measure your waist) then check the manufactures sizing charts to ensure you purchase the correct size. You will also want to think about the type of waistband you prefer, for example are you okay with elastic waist bands or do you need them to be cloth-covered.

Cut– There are a couple of different cuts of boxers to be aware of

  • Classic cut- Will be neither too baggy nor too fitted.
  • Full cut means that they will be fairly loose and perhaps a bit baggy
  • Tapered means that it will be a more fitted look. The leg opening may also have a rise on the side