Men’s Boxer Shorts: How To Choose the Best Boxers

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The 1990s and 2000s were all about boxer shorts. Growing up as a millennial, in high school and at university, guys only wore boxers. Boxers were cool, fun, and the only underwear style you could wear if you wanted to fit in. Underwear and boxers were synonymous with each other and that was that.

Then came the 2010s and men proclaimed it the decade of the boxer brief. Now entering the 2020s (the year 2020 was quite the welcome, eh?), and we are witnessing another shift in men’s underwear style towards trunks. My bold prediction is by the end of the 2020s, briefs will become mainstream again.

So where does that leave fans of men’s boxer shorts? Relegated to the bottom of most underwear websites today. But fear not! Since men’s underwear appears to run in a cyclical pattern, you’ll have your moment in the sun again sometime between the years 2030 and 2040. And if you believe the popular (yet false!) stereotype, that will also be about the time you decide to buy new underwear.

I am definitely kidding about that last sentence – men are treating their underwear much more seriously today than before – but unfortunately, not about everything else before that. Boxer shorts are definitely considered outcasts by most underwear brands today. Selection is dwindling and some brands don’t even bother manufacturing boxers anymore. 

Nonetheless, there is plenty of selection out there and unlike the 1990s and 2000s, boxers today are as modern and comfortable than ever. Diverse materials, improvements in design, and innovative features – all carried over from research in boxer briefs – mean today’s boxer shorts are lightyears ahead of yesterday’s boxers. This is fantastic for you, yet may also mean confusion amid a bewildering amount of options.

Let this guide carry you to your utopian – not utilitarian – pair of boxers!


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Men’s Boxer Shorts Length: Short or Long?

Boxer shorts come in a variety of lengths, so to start, we first need to define the inseam. The inseam is simply the length from the crotch to the bottom of the leg opening. When shopping for pants, men commonly know this as the length. If you wear 32×32 pants, your waist size is 32 inches, and your inseam length is 32 inches as well. The same concept applies to men’s underwear.

When it comes to boxer shorts, there is no universal length that defines boxer shorts. However, most American brands will design boxers with a 4-6” inseam. This is also generally the length of boxer briefs for comparison, which makes sense if you think about it. Having said that, unlike shopping for boxer briefs, many brands won’t mention the inseam length while shopping online. Thus, you’ll have to assume somewhere between 4-6” unless otherwise said. 

Comparison of men's underwear inseam lengths
Most boxer shorts are 4-6″ long for comparison.

On the shorter side of the spectrum, Mack Weldon offers boxers with 3.75” and 4” inseams (18-Hour Jersey Knit Boxers and 24/7 Woven Boxers, respectively). MeUndies also offers 4″ inseam boxers. In the middle of the road, Pair of Thieves and Saxx both offer 5” inseams. Tommy John’s boxers have a 6” inseam on the longer end of the spectrum, while David Archy’s boxers are a whopping 8″ long. I wouldn’t wear David Archy’s boxers under clothing – use them more as shorts to wear around the house.

Quick tip: Ask yourself when you will be wearing boxers. Some guys wear boxers as their daily underwear style. If this applies to you, then you’ll want shorter lengths (+/- 4″) to avoid material bunching in your pants. On the other hand, for lounging or comfy sweats, you may wish to purchase boxers with longer lengths for more aesthetic purposes, akin to wearing shorts, especially if you have kids.


Men’s Boxer Shorts Width: Regular or Slim-fit?

In addition to length, you will also need to consider the fit of your boxers. Do regular boxers work for you, or do you need slim-fit boxers? This choice is unique to boxer shorts wearers as guys wearing briefs, trunks, and boxer briefs are, by definition, wearing slim-fit underwear. And yet this is a very important decision!

Slim-fit boxers are like slim-fit shirts: they will fit snugly around your hips, butt, and thighs. They won’t be as tight as boxer briefs, as they are boxer shorts and allow for airflow and freedom. However, like slim-fit shirts, they will restrict some movement. And if you have ever felt constricted just seeing a muscular guy try to wear a slim-fit shirt, you’ll understand why slim-fit boxers and guys with muscular legs don’t mix well.

On the other hand, slimmer and thin guys will want to purchase slim-fit boxers. The excess fabric around the legs on regular boxers won’t show well on thinner guys; it will look like the 1990s, and wearing clothes too big for you. I’m sorry, you can’t wear that in the 2020s. Furthermore, excess fabric from boxers will bunch up when you wear slimmer pants, creating a huge comfort problem.

Quick tip: For thinner and slimmer guys, slim-fit boxers are the best choice, especially if wearing slim-fit pants (although, I would encourage you to wear boxer briefs or trunks or even – gasp! – briefs when wearing slim-fit pants). Slim-fit boxers will look modern and better for you. At the other end, muscular guys – especially those with beefy legs – need to be wearing regular boxers; slim-fit boxers will constrict your movement too much. It will become uncomfortable and negates the reason to wear boxers – for freedom and air circulation. Slim guys can also choose to wear regular boxers, for example, when lounging around in boxers on the weekends or when sleeping. Make sure to choose wisely!

Quick Tip: As much as I would love to say to go with slim-fit boxers, I imagine most guys will want to stick with regular-fit boxers. The reason is guys who buy boxers want freedom and airflow, and slim-fit boxers don’t provide as much as regular-fit boxers. The exception is if you wear tighter pants, especially dress slacks or skinny jeans, and insist on wearing boxer shorts instead of tighter underwear, then go with slim-fit boxers. Slim-fit boxers won’t bunch up as much under tight pants, and since your pants already restrict freedom and airflow, slim-fit boxers won’t make any difference in this regard. Of course, I recommend wearing tighter underwear under dress pants and skinny jeans, including – dare I say it, if you are wearing boxers – wearing briefs.



Tapered or Not Tapered?

Besides regular vs. slim-fit boxers, another question for boxer shorts lovers is tapered vs. non-tapered boxers. Tapering means that the fabric of the legs comes further up the leg on the sides compared to the front and back.

Tapered boxers allow for a bit more leg freedom of movement than regular boxers. While this isn’t so much of a concern with regular boxers, it can be noticeable with slim-fit boxers since, as I mentioned above, slim-fit boxers restrict leg movement. Additionally, tapered boxers can be slightly better under tighter pants because there is slightly less fabric.

Quick tip: Tapered boxers are mostly a style preference. And because there is a very limited collection of tapered boxers, you won’t have much choice in terms of colors/patterns, materials, or brands. Unless you love the look of tapered boxers or really need that extra freedom of movement, stick with non-tapered boxers for the best selection.

Price

Many specialty and luxury men’s underwear companies arrived in the past few years to give men many more options in buying underwear. However, unlike the days of buying Hanes or Fruit of the Loom multipacks from Target or Walmart, specialty underwear companies can often charge the same price for one pair as a Hanes three or six-pack. In other words, buying a week’s worth of men’s boxer shorts can easily top $100!

That is why it pays to do some homework and one of the reasons MensUnderwearGuide.com exists. In general, here is how we evaluate prices:

  • $ = each pair costs less than $5. Underwear in this range is more functional than luxurious and tends to attract mainstream companies such as Hanes and Fruit of the Loom (FTL). Expect a limited selection of cotton fabrics and simple plaid patterns and colors. Don’t expect pairs to last long; to get the cost down, fabric and manufacturing processes are on the cheaper end. We’ll call this range the “underwear minimalists.”
  • $$ = each pair costs between $5 and $15. This range is the “middle class” of underwear, and you’ll find both high-end products from cheaper manufacturers and lower-end products from high-end manufacturers. However, as prices rise, selection in this range is narrowing; most of the good styles are now in the $15-25 range (see below). Nonetheless, if you are wearing Hanes or FTL and want something more sophisticated, this is the price range to start your new journey and experiment before getting pricier pairs. Brands like Calvin Klein (cotton classics), David Archy, and others will charge you in this price range.
  • $$$ = each pair costs between $15 to $25. Above $15, brands aren’t selling you underwear; they are selling you a lifestyle. If you haven’t shopped in this price range before, you need to read this guide and study your options. You’ll want to shop above $15 if comfort and style are far more important than “just needing underwear,” especially if you want softer and nicer fabrics than just cotton. Men will find brands like Chill Boys, MeUndies, and Bamboo Cool in this price bracket.

Chill Boys Boxers
  • $$$$ = each pair costs greater than $25. Boxers in this range are the business class of men’s boxer shorts. You’ll find specialty underwear companies up here, such as Mack Weldon, Saxx, Tommy John, and Tani. There is no messing around when you are paying $30-$40+ per pair of boxers. If you don’t know what you want, I recommend trying boxers from a lower price range first or buy when brands offer sales in the $25+ range category. For example, both Mack Weldon and Saxx offer bulk discounts when buying at least 3-7 pairs. Tommy John and Tani, on the other hand, offer sales throughout the year, allowing you to try them out without needing to pay full price.

Quick tip: For boxer shorts, I find that $10-$20 per pair is generally the sweet spot between comfort, design, and not paying a fortune for boxers. Yet, you will get higher quality products from brands in the $25+ range, so wait until sales occur and then try them out. Or, if you want to buy one or two pairs at full price now to try, and if you like, then when the sales hit, buy, buy, buy! You’ll stock up with higher-end pairs at great prices.


Colors and Patterns of Men’s Boxer Shorts

Unlike other underwear styles, men’s boxer shorts have always been available in a wide variety of colors, patterns, and prints. Growing up in high school and college (I’m a millennial), other guys wore many different colors and pattern variations (solid colors, stripes, plaids), and some even wore fun prints (remember cartoon-themed boxers?). 

Interestingly enough, while brands are greatly increasing color and pattern selections for briefs, trunks, and boxer briefs, selections for boxer shorts are decreasing. No doubt this is due to the strong trend of guys switching away from boxer shorts to tighter cuts, including current champ boxer briefs. This is a case of simple economics: less demand for boxers means less supply. In fact, some famous brands today do not offer boxer shorts at all.


I really prefer you don’t wear boxers like these, unless you really want to make a statement!


Quick tip: Smaller selections of boxers make purchasing men’s boxer shorts easier, especially since the boxer universe concentrates on dark, solid colors. These colors show well for most guys and appear the most modern. I recommend staying with blues, blacks, and dark grays. Patterns generally are fine, although I suggest subdued patterns like a plaid over bold patterns (cartoon images, boxers with logos). Especially with boxer shorts, you want to stay away from the 1990s look in the 2020s. Having said that, if you really want to wear fun-looking boxers, go all out! 🙂


Man wearing MeUndies men's boxers in black

Dark colored boxers – like these black bamboo MeUndies boxers – work well for any occassion and won’t go out of style.



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Material and Fabric

For men’s boxer shorts, the only choices used to be woven or knit boxers. Knit boxers are softer yet thicker, while woven boxers are thinner but not as soft. The choices were very clear-cut and simple, yet didn’t provide many options for comfort. Today is far different.

As I mentioned above, as men move away from wearing boxer shorts, options overall are decreasing. However, in the world of fabric, brands are adopting fabrics used in boxer briefs and developing boxer shorts with a plethora of materials. Modal, elastane, and polyester blends are now commonplace among mid-range to higher-end brands. Options for softness, moisture-wicking, and stretch allow guys to choose boxers for their precise comfort.

Although possibly more overwhelming than woven or knit options, I have broken it down for you. Here are some popular materials that are worth experimenting with:

  • Cotton: I am placing cotton first because, chances are, you are wearing cotton underwear right now. Unlike boxer briefs and briefs, a lot of boxer shorts are 100% cotton because adding elastane/Spandex to provide stretch isn’t necessary. On the other hand, cotton is one of the heavier materials in the world of underwear, so while many praise cotton for its “breathability,” you will generally be able to “feel” cotton blends when wearing them.
    • Note that many “heathered” boxers on the cheaper end from Hanes and Fruit of the Loom use a 75% cotton/25% polyester blend, while solid colors use a 100% cotton blend. If you don’t want to wear polyester, make sure to stay away from heather patterns or double-check the fabric content.
    • 100% cotton boxers are on the high-end and low-end boxer shorts spectrum. I don’t mind cotton for boxers as much as I do for tighter men’s underwear – I refuse to wear cotton boxer briefs – but I still believe bamboo and modal are better options (keep reading).
  • Bamboo: Some companies are selling underwear using bamboo as a substitute for cotton, such as Chill Boys, as bamboo often is more eco-friendly than cotton. I gushed over bamboo underwear in my review of Separatec’s bamboo briefs so I highly recommend its softness. The same rules apply here for cotton, especially when seeing the mix of elastane or Lycra in the fabric blend.

Chill Boys Boxers


  • Modal: According to Masterclass, modal is a “semi-synthetic fabric made from beech tree pulp.” Masterclass also notes that modal is “luxurious” due to its “soft feel and high cost.” I completely agree. Modal underwear is going to be in the $$$ or $$$$ categories, and if it is cheaper, be careful that the manufacturer did not heavily blend modal with more inexpensive materials (I’ve seen some modal pairs with less than 50% modal!). Yet, modal has been, for years, my favorite material – besides bamboo – because of how lightweight and thin it is, yet still feeling softer than cotton. But despite its thinness, my Calvin Klein modals have held up exceptionally well, even after years and years of wear.
  • Polyester/Microfiber/Mesh: On the other end of the spectrum from the cotton/modal world are the synthetic blends, which feel “slippery” compared to cotton or modal. Nylon, polyester, and polyamide – a nylon derivative itself – are the most common fabrics in this category. Athletes wear synthetic blends because they are lightweight like modal, yet run cooler and dry much quicker than modal or cotton. Therefore, a perfect match when athletes sweat a lot is beneficial for guys working in hot climates, hiking, or traveling.
    • But note that polyester styles are not 100% polyester; often, they include 10-15% of stretchier fabric such as elastane. A higher percentage of elastane means a stretchier (and more comfortable) pair. Thus be careful when buying 100% polyester or 75% cotton/25% polyester boxers because these boxers do not contain any elastane or Spandex and, thus, aren’t going to feel that great compared to other boxers.

Quick tip: As with boxer briefs, pay attention to the amount of elastane (or Lycra or spandex) in the fabric blend, as a higher amount of elastane will provide more stretch, better fit, and overall more comfort. Since boxers aren’t as tight as boxer briefs or briefs, try to have 5% Spandex/elastane content, at least, especially if they are cotton boxers. But if you value softness – especially if you wear boxers while lounging – modal and bamboo are your ideal fabrics.

Why should you stop wearing cotton underwear?

Flys: Button or Slit

Flys are a much more controversial debate for boxer briefs, trunks, and briefs as many models no longer have functional flys. For guys used to using their fly to pee, not having a fly can be a strange experience (although one I quickly overcame). Yet this debate isn’t present in the world of men’s boxer shorts, as almost all boxers come with a fly. Instead, the main question is whether you prefer a button on your fly or just an open slit.

  • Button fly: One or two buttons on the fly keep it closed when not in use. To pee, however, you must unbutton your boxers to experience nirvana at the urinal.

SilkCut Slim Boxers with Button Fly

Tani’s Silk Cut boxers come with a button fly.


  • Slit fly: This is the “standard” vertical fly that most guys recognize when seeing a fly. There is no button, as overlapping fabric provides closure. You’ll have to pull fabrics to open the slit to access your penis.

Learn about the different fly types for men’s underwear on my YouTube channel.

Quick tip: I have worn boxers (and boxer briefs!) with button flys, and I didn’t understand the concept. It felt like more work to use the fly than just the regular vertical or horizontal flys, which is my preference when using a fly (although I don’t typically use flys anymore to pee). Furthermore, on my cheap underwear with button flys, the button would come undone during the day, making it useless and pointless. Having said that, if you don’t use a fly to pee (you go over your waistband), then having a button fly is useful as it keeps the fly closed so your penis doesn’t flop out. Just make sure to purchase higher-end underwear if you prefer a button fly to ensure the construction holds together.


Ball Pouch

As long as we are on the subject of penises, your penis, and balls need a home. But not a home they share with the rest of your groin area, their separate space. That is what pouches provide – a guest house or converted basement for your penis separate from the main house.

For me, pouches make a big difference in comfort when wearing tight underwear styles. Most of my underwear has some sort of pouch, yet I feel it right away when I wear pouchless boxer briefs. Everything seems more squished, and overall it all feels tighter. And honestly, I am not even that big!

However, does a pouch matter when wearing men’s boxer shorts? After all, boxers are designed to be roomy; why the need for extra room? Consider looking at it another way. Briefs, trunks, and boxer briefs provide support to your balls and penis by providing a cradle underneath, whereas boxers do not. This difference in the vertical space between the crotch of your underwear and your balls is what makes boxers feel roomier. 

Yet, depending on the brand and style, boxers may not provide much additional horizontal space around your penis and balls. Especially with today’s slim-fit boxers gaining popularity, the extra horizontal space a penis pouch provides is what adds additional comfort to boxers.

Quick tip: While I believe having a pouch is a must-have for briefs, trunks, and boxer briefs, it is more of a luxury item for boxers. Not all brands have a pouch feature for their boxers, although higher-end brands may do. Unless you are specifically buying slim-fit boxers, I wouldn’t stress over not having a pouch. And even if you are buying slim-fit boxers, it may not necessarily be as important to you compared to tight underwear styles.


Branded Waistband

When I was growing up, it was popular in school to sag your pants (fellow millennials know what I am talking about!), so your underwear waistband (and usually more) always showed to the public. Nowadays, guys are into tighter clothing, so often, your pants entirely cover your boxers.

Nonetheless, personal preference may dictate whether you want your underwear to be a sales ad for a particular brand. Some brands are well known for their waistbands, such as Calvin Klein, American Eagle, Ethika. Other well-known brands don’t even put their name on their waistband, such as Mack Weldon. For the most part, this is purely an aesthetic choice rather than a choice of comfort.

How to hide the waistband logo on your underwear.

Waistbands can impact comfort; however, it may be hard to determine this when shopping online. Primarily it is due to the fabric on the interior of the waistband, although most companies won’t show this material online. Brands may also advertise their waistband’s unique features, such as no-roll (the waistband won’t fold over) or luxurious fabric (it feels soft). These added features may help provide additional comfort, especially if you have skin sensitivity or are at the upper end of your size bracket (for example, if you have a 34” waist and are buying medium size).

Quick tip: Branded waistbands are purely a personal design choice, and unless you are showing your boxers off a lot, no need to waste time studying waistbands when deciding which pairs to purchase. On the other hand, mid-range and high-end brands will provide more comfortable waistbands than lower-end pairs, and if you are sensitive to waistband comfort, you may want to focus more on higher-end brands. I do not pay much attention to waistbands as I believe more essential factors contribute to choosing a great pair of men’s boxer shorts.


Multipacks of Men’s Boxer Shorts

Multipacks – two or more pairs bundled together for purchase together – can provide significant value to you if purchased correctly. First, I am not talking about the three or six-packs in Target and Walmart (seven-packs if you include that extra pair included for free!). I am talking about mid-range and higher-end brands providing two or three-packs for a slightly lower price per pair than buying each pair individually. Thus, multipacks are a fantastic way to save on buying brands and styles you already love. However, you must do a tad bit of homework to ensure you are saving.

That first piece of homework is ensuring you are indeed saving money. For example, Tommy John sells their Second Skin boxers for $36/pair or a three-pack for $108. Simple math shows that each pair in the three-pack is still $36. Thus, you are not saving money by purchasing the multipack, but in exchange, you are giving up some freedom by not picking out the colors and patterns you genuinely want. In this case, just purchasing the single boxers for $36/each and getting the colors and patterns you love is the winning play.

Assuming you are saving money by purchasing the multipack, however, compare the money you save to the limited design choices multipacks provide. If you aren’t happy with the colors the multipacks come in, is it worth saving the money compared to purchasing the single pairs in the designs you want? On the other hand, if you like the choices for multipacks, it is a great way to stock up for a lower price.

Additionally, if you are trying out a new brand or style, especially at higher-end pricing, it may be best to purchase one or two pairs first to ensure you like it before committing to multipacks. While the multipack may offer a lower price per pair, you still have to pay more money to purchase three pairs at once instead of just one pair. If you end up not liking it, that is money – and underwear – wasted.

Quick tip: Only consider multipacks once you know you like (preferably love!) the brand and style. Assuming yes, calculate the price per pair when purchasing a multipack compared to buying single pairs and weigh this with the multipack’s design options. Sometimes this trade-off is a fantastic deal; other times, there is no deal at all. Lastly, if your favorite brand is having a sale and giving a good deal on multipacks, consider going on a multipack shopping spree to stock up for excellent prices. Great men’s boxer shorts do not have an expiration date, so it is ok to have new pairs on reserve in your closet for future use.




Design Country

Boxer shorts as underwear is not only on the decline but also a more American-centric way of living. Outside of the United States, men’s underwear is skewed towards briefs and trunks, with even boxer briefs not being as common. Hence, unlike with briefs and trunks, where it pays to shop international brands, it is almost a non-starter for purchasing boxers.

I almost deleted this section entirely from my guide on men’s boxer shorts because there is little value in shopping internationally for boxers. Nonetheless, I wanted to keep this in because of a small yet important, warning. Many non-American brands will sell you “boxers” online, often trunks or boxer briefs, but not boxer shorts. 

There is nothing shady at all going on here. In other countries, there are two primary types of men’s underwear: briefs and underwear a bit longer than briefs. As American culture spread internationally, longer varieties came to be known as “boxers” in most cultures. Yet, as other countries skew towards tighter styles, what we call trunks or boxer briefs remained just “boxers” elsewhere. Hence, my warning that if you truly desire boxer shorts, be careful when ordering on international websites that you are truly buying boxer shorts.

Quick tip: I love shopping for underwear internationally as it opens up a diverse world of styles and patterns. But this is really only true for briefs, trunks, and boxer briefs. When shopping for boxer shorts, stick with American brands as there is very little selection outside the United States (there is already declining selection within the U.S.!).


Conclusion

Finding a fabulous pair of men’s boxer shorts feels terrific. And it doesn’t have to be hard. By breaking down the essential factors in comfort and style of men’s boxers in this guide, I hope you will feel more confident searching online (or in-store) for pairs that are right for you. I also hope you will be encouraged to experiment and add variety and spice to your underwear collection. To recap, here are the criteria I covered in this guide:

  • Boxer Shorts Length (Short or Long)
  • Boxer Shorts Width (Regular or Slim-Fit)
  • Price
  • Colors and Patterns
  • Material and Fabric
  • Flys: Button or Slit
  • Penis Pouch
  • Branded Waistbands
  • Multipacks
  • Design Country

I would love to hear from you! Are you still a die-hard boxers fan? Do you alternate between boxers and boxer briefs or trunks? Let me know your feedback in the comments below.


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Eric at MensUnderwearGuide.com

Eric is the creator and writer of MensUnderwearGuide.com. He loves boxer briefs and trunks, exploring the new world of briefs, the soft feeling of modal and the lightness of mesh microfiber, and of course writing and researching the world of men's underwear.