Tommy John Men’s Underwear: A Comprehensive Guide

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Author’s Note: I purchased all of my Tommy John underwear myself using my own money.

I am not shy spending lots of money on men’s underwear – I have over 120 pairs. And several of those pairs cost me quite a bit, in the $30-40 per pair range (and no, they aren’t Calvin Klein, which is often a lot cheaper). However, my high-end underwear has been primarily from Mack Weldon, Saxx, and Silk Cut. While I had heard of Tommy John, of course, I had never bought any Tommy John men’s underwear. So I decided to splurge and buy four pairs to try them out. (Update July 2026: I purchased three more pairs: one Cool Cotton brief, one Second Skin trunk, and one Air brief.)

Overview of Tommy John Men’s Underwear

I own seven pairs of Tommy John Underwear: one pair of Second Skin two-inch trunks, one pair of Second Skin boxer shorts, one pair of 360 Sport six-inch boxer briefs, one pair of Air four-inch boxer briefs, one pair of Second Skin four-inch trunks, one pair of Cool Cotton briefs, and one pair of Air briefs.

I am happy with all seven pairs. However, since I am not a boxer shorts guy, I don’t wear my Second Skin boxer shorts much at all. On the other hand, the two Air pairs are my favorite, followed by the Second Skin four-inch trunks. I really like Tommy John Air underwear.

Tommy John Men’s Underwear is on the premium side of men’s underwear, usually costing $30 to $40 per pair. If you value quality and comfort and take good care of your underwear, then the investment is well worth it. I am delighted with my Tommy John men’s underwear for several reasons.

Learn More: Tommy John Men’s Underwear

Unnoticeable Underwear

One thing I think about when testing a new pair of underwear is whether I notice I am wearing it. If I don’t notice it, that is a big positive. You shouldn’t be thinking about your underwear when it is on because chances are, you are thinking about how uncomfortable it is. As such, if I’m paying $30+ for a pair of underwear, I don’t want to be thinking about how uncomfortable I am!

The excellent news is that all four Tommy John lines pass this test: Second Skin, 360 Sport, Cool Cotton, and Air. I didn’t think about them when I was wearing any of my Tommy John underwear. One minor exception is that I did find the Tommy John Second Skin boxer shorts uncomfortable because they were bagging up under my slim pants, unlike the Second Skin trunks. However, wearing the boxers without pants was very comfortable, especially when sleeping.

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Tommy John’s Horizontal Fly Might Be the Best

I don’t usually use my underwear fly, and most of my underwear is fly-less. I always pee by going over the waistband. However, that doesn’t mean I don’t use a fly occasionally, especially when testing out new underwear. While the vertical fly is the “standard” men’s underwear fly, the horizontal fly is quickly gaining momentum.

Tommy John features its “Quick Draw” horizontal fly on all of its underwear, and I love it. The horizontal fly is very intuitive and easy to use. I don’t like the vertical fly because it requires moving fabric around to get to your penis. That is why I find it so much easier to pee over the waistband. And if you think about it, a horizontal fly is the same movement as going over the waistband!

I do have other horizontal fly underwear, and the size of the opening is critical. If the opening is too small, it will be harder to reach your penis and pull it out. I really like Tommy John’s horizontal fly design because the opening is quite large, making it very easy to reach in and pull out. Honestly, it might be the best fly design I have tested.

Having said that, a note of caution: if you are larger, or you are a grower, it can be relatively easy for you to slip out of the opening. There is a flap behind the horizontal opening that you can tuck yourself into to somewhat prevent this. But it seemed to slip out relatively easy when growing for me, so just keep that in mind, especially if you intend to just wear underwear around the house.

The Design of Tommy John’s Hammock Pouch

Tommy John has its own proprietary, separated pouch design called the Hammock Pouch. The Hammock Pouch is a V-shaped pouch that I find very comfortable, along the likes of Saxx’s I-shaped pouch and the Hanes Total Support Pouch. The Hammock Pouch is designed well and provides support, instead of being uncomfortable or in the way that I find some U-shaped pouches.

Note that Tommy John offers the Hammock Pouch only on select versions of its trunks and boxer briefs, primarily the 360 Sport, Second Skin, and Cool Cotton collections. The Hammock Pouch is not available on its briefs, and for obvious reasons, not its boxer shorts. However, unlike Saxx which features its BallPark Pouch on all of its underwear, Tommy John gives you the option of whether you want the pouch or not. This is great for guys who aren’t into specialized pouches and prefer the no-nonsense regular pouch.

Yet, in an interesting decision, Tommy John charges $2 extra per pair of underwear to “upgrade” to the Hammock Pouch instead of a conventional pouch. No other men’s underwear company that I know of explicitly charges extra for the pouch. If you really like having the separated pouch, the $2 extra charge is worth it. However, if you aren’t sure or don’t really care about separated pouches, you can skip the extra charge.

Tommy John Men’s Underwear Naming Convention

It is crucial to understand how Tommy John labels its men’s underwear, because it is somewhat unconventional:

• Briefs are briefs, so no change there. Tommy John’s briefs are more towards the full-cut side of the briefs spectrum, compared to the modern hip brief styles, especially those of Calvin Klein. If you’re looking for more hip coverage in your briefs, then Tommy John is more your style. (Read my Guide to the Best Men’s Briefs to learn more about switching to briefs.)

See More: Tommy John Air Briefs.

• Square-Cut Trunks are what Tommy John calls its trunks with a 2″ inseam. Europeans and Brazilians will find these square-cut trunks a tad longer than the 1″ inseam that generally describes square-cuts. However, Americans looking to explore trunks will find the 2″ inseam ideal.
• Trunks are what Tommy John names its 4″ boxer briefs. Yes, I said “boxer briefs.” I label any pair of men’s underwear with a 4″ inseam as a boxer brief, and Tommy John’s “trunks” are essentially shorter boxer briefs.
• Mid-Length is Tommy John’s name for 6-inch boxer briefs, which are the standard American boxer briefs. If you’re looking for boxer briefs, get the Mid-Length boxer briefs.
• Boxer Briefs, instead, refer to Tommy John’s 8-inch boxer briefs. Generally, eight inches is way too long for regular boxer briefs. Instead, I label anything 7″ and longer to be “long-leg” boxer briefs, which are what these are. Long-leg boxer briefs are suitable for guys who need more leg coverage, whether that is due to chafing issues, athletic support, or those who have thicker thighs and want to prevent ride up. Read my Guide to Long-Leg Boxer Briefs if you are interested in this style.
• Relaxed Fit Boxer is the name of Tommy John’s boxer shorts with a 6″ inseam. As I note a bit later in this post, Tommy John’s boxers are full-cut, meaning they have wider leg openings. While this is comfortable for lounging, it also means there is more fabric to bunch up under your pants. Contrast this to “slim-fit” boxers that have smaller leg openings but are less prone to bunching up.

I want to make specific note of these labels so you don’t get the wrong pair!

Tommy John Men’s Underwear Collections

Tommy John has five main men’s underwear collections, of which I own four: Second Skin, 360 Sport, Cool Cotton, and Air. Those four comprise the bulk of Tommy John’s underwear lineup. The fifth collection – DriComfort – is new as of 2026, so I haven’t tried it out. Technically, Tommy John has a sixth collection called Second Skin Luxe Rib, but I just consider that an off-shoot of the Second Skin collection.

Second Skin Collection

Tommy John’s Second Skin underwear is its most popular lineup, and for good reason. Crafted from a luxurious blend of 90% micro Modal and 10% Spandex, these underwear options are silky-soft, lightweight, and breathable. I always recommend modal and bamboo underwear having at least 5% Spandex content, and Tommy John doubles that by providing 10%.

I personally own the Second Skin square cut trunks and boxer shorts. The trunks are perfect for everyday wear, whether at the office or at home. Fabric is soft, waistband is great, the pouch is comfortable, and the fly is ideal for guys who use flys. Also, these Second Skin trunks do not have any butt seams, which is a nice touch. Finally, I didn’t have any issues with riding up (read my Guide to Preventing Boxer Briefs Riding Up here).

See More: See all of Tommy John’s Second Skin Underwear here, such as these Navy Blue Mid-Length Boxer Briefs.

However, if you really prefer thin, lightweight underwear, I would look further down at Tommy John’s Air collection. I prefer the Air collection over the Second Skin because Air is much lighter and feels like nothing. Second Skin is better than cotton, and I do like Second Skin for sure. However, for guys who love thin, lightweight underwear, Air is the better choice.

While the two-inch and four-inch trunks provide a fantastic snug fit, perfect under jeans or tailored pants, the boxer shorts are a different story. They’re undeniably soft and lightweight, but I found them too baggy for everyday wear under pants—they bunched up uncomfortably. These are not “slim-fit” boxers, which can help reduce bunching up, but full-cut boxers. However, as lounging shorts around the house, they’re superb and perfect for Netflix and chill weekends.

Second Skin Details

• Styles: Second Skin is only one of two Tommy John lines available in all styles: briefs, square-cut trunks, trunks, boxer briefs, and long-leg boxer briefs…and boxer shorts for guys who love boxers. (See all Second Skin styles at this link here.)
• Fabric: 90% micro modal and 10% Spandex. Very soft and ideal replacement for cotton or bamboo. Note that the heathered colors feature some polyester. Also, Tommy John has a “Luxe Rib” version of the Second Skin collection that features 49% viscose, 43% modal, and 8% Spandex. The Luxe Rib version is supposed to have extra airflow, according to Tommy John.
• Colors and Patterns: As Tommy John’s most popular lineup, expect a wide variety of colors and patterns, especially for its trunks and boxer briefs. Second Skin briefs have a good variety of solid colors, but no patterns.
• Price: $36-40. Tommy John has sales throughout the year, so best to stock up then. While Tommy John offers three-packs for sale, do not assume it saves you any money. Also, Tommy John sells select styles on Amazon, so you can compare pricing between Tommy John’s website and Amazon.

Product prices and availability are accurate as of 2026-08-25 at 13:58 and are subject to change. / Affiliate links.

360 Sport Collection

I love the feeling of good athletic (non-compression) underwear! My Puma Performance Boxer Briefs are my low-priced go-to boxer briefs. I also wear Under Armour’s BoxerJocks for an upgraded experience. Tommy John’s 360 Sport boxer briefs (with a 6-inch inseam) are an excellent choice for a more luxurious pair. Made from a stretchy microfiber blend (88% polyester, 12% spandex), they are durable, smooth, and feature targeted mesh zones for breathability.

If you’ve ever worn Puma Performance Boxer Briefs or Under Armour BoxerJocks, you’ll find Tommy John’s 360 Sport boxer briefs similar. Compared to Puma’s Boxer Briefs, Tommy John is definitely a couple of steps better (and a couple more steps more expensive). But compared to Under Armour, Tommy John’s 360 Sport is about the same in my opinion. In fact, I would say Under Armour’s material is slightly more silky smooth than 360 Sport.

However, for guys who love using a fly, 360 Sport boxer briefs are superior due to Tommy John’s thoughtful horizontal fly design. Tommy John has absolutely perfected this feature, offering an intuitive and wide horizontal fly that makes quick restroom breaks during workouts hassle-free. Under Armour only offers a vertical fly on their BoxerJocks.

See More: See all of Tommy John’s 360 Sport Underwear here.

360 Sport Details

• Styles: 4-inch, 6-inch, and 8-inch boxer briefs. No briefs, sorry. (See all 360 Sport Underwear at this link.)
• Fabric: Microfiber blend of 88% polyester and 12% Spandex. Any microfiber blend with more than 10% Spandex is good in my book, so these 360 Sport boxer briefs qualify. Microfiber is a slippery fabric, what you would expect when thinking of “athletic” underwear. However, I would say that
• Colors and Patterns: Solid colors only, although some prints have a bold, neon waistband color, which I love. My black 360 Sport boxer briefs are pretty boring in comparison (although they have a weird print on the left leg not present in newer versions).
• Price: $30-$32 per pair. This is towards the higher end of men’s underwear, and a bit more expensive than comparable Under Armour BoxerJocks. However, if you can wait until Tommy John has a 20-30% sale, then snag each pair for $21-26/pair. Prices under $25/pair is in line with Under Armour’s BoxerJocks.

Product prices and availability are accurate as of 2026-08-25 at 13:58 and are subject to change. / Affiliate links.

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Air Collection

My absolute favorite Tommy John underwear line is the Air collection. I own both the 4-inch inseam trunks and the briefs and I love them both. Crafted from an ultra-lightweight, airy nylon and spandex micro-mesh blend, these trunks literally feel like you’re wearing nothing at all. They’re stretchy, super thin, and incredibly breathable—ideal for hot climates or travel.

Readers know that I love lightweight underwear, especially those made from mesh, bamboo, and modal materials. These Air trunks are some of the lightest-weight underwear I own. Additionally, they’re so stylish and fit perfectly, offering just the right amount of support without being restrictive. And they look fantastic – perfect for date night!

See More: See all of Tommy John’s Air Underwear here.

Tommy John Air Details

• Styles: 4-inch, 6-inch, and 8-inch boxer briefs…and briefs! Guys looking for briefs can take advantage of Tommy John Air Underwear, too.
• Fabric: The micro-mesh fabric is made from 77% nylon and 23% Spandex. This is Tommy John’s lightest fabric, and it dries rapidly. Note that while Air underwear is quick-drying, it may not be suitable for athletic use because the thin fabric also provides limited support compared to 360 Sport underwear.
• Colors and Patterns: Almost always solid colors in the blacks, grays, and blues. Occasionally, there might be a pattern based on these three colors.
• Price: $38-$40 per pair, which is the upper end of the pricing range for men’s underwear. However, Air is definitely a premium line from a premium brand. If you like Air underwear, stock up during one of Tommy John’s sales.

Product prices and availability are accurate as of 2026-08-25 at 14:04 and are subject to change. / Affiliate links.

Cool Cotton Collection

For those who prefer cotton but still want a premium experience, Tommy John offers its Cool Cotton collection, crafted from 86% Supima cotton and 14% Spandex. This blend is breathable and keeps you cooler than traditional cotton underwear. I generally don’t wear cotton underwear, since I far prefer bamboo and modal. But I recently picked up two pairs of Air underwear and I threw in a pair of Cool Cotton briefs to try out.

They aren’t bad at all, especially if you like cotton. However, for me personally, I far prefer the Air and Second Skin collections. I just find cotton too thick for my tastes, as I really prefer thin, lightweight underwear. But if you are into cotton, I can’t really say anything bad about the Cool Cotton briefs.

For this price, you’ll want to compare it to Mack Weldon’s 18-hour Jersey underwear. Alternatively, consider something more affordable yet still as comfortable and stylish, such as David Archy Bamboo Boxer Briefs or Calvin Klein Modal Boxer Briefs. Or read my Guide to the Best Boxer Briefs on Amazon here.

Product prices and availability are accurate as of 2026-08-25 at 20:35 and are subject to change. / Affiliate links.

Tommy John Cool Cotton Details

• Styles: Cool Cotton is the other Tommy John lineup available in all styles. All men can find their style with Cool Cotton, ranging from briefs to all lengths of trunks and boxer briefs to boxer shorts. Note that I have the briefs and they are a wider cut than the modern “hip-brief” style. The briefs provide more hip coverage than what you may be expecting if you are used to wearing Calvin Klein briefs, for example. But if you are used to wearing “full-cut” Hanes or Fruit of the Loom briefs, these are slightly more revealing than those.

Buy now: Cool Cotton Briefs

• Fabric: 86% Supima cotton and 14% Spandex. 14% Spandex content is very high for cotton-based underwear. And combined with Supima cotton, specifically – a softer version of cotton – these are probably some of the nicest cotton underwear pairs you’ll own. They will be more stretchy and quicker drying than 100% cotton pairs.
• Colors and Patterns: Cool Cotton has the most colors and patterns available of Tommy John’s men’s underwear, other than Second Skin. If you like variety, you’ll have plenty to choose from, but still less than other premium brands like Saxx and Mack Weldon.
• Price: $32-36 per pair, which is in the middle of Tommy John’s lineups.

See More: Tommy John’s Cool Cotton men’s underwear.

DriComfort Collection

DriComfort is Tommy John’s newest underwear lineup. DriComfort features standard 4-inch, 6-inch, and 8-inch boxer briefs. (Read my Guide to Long-Leg Boxer Briefs here.) Apollo underwear features the “drirelease” fabric blend (7% polyester, 14% modal, 7% spandex) that Tommy John claims keeps you significantly cooler than standard cotton. In fact, Tommy John says the fabric is “seven degrees” cooler than cotton. In theory, Apollo is a middle ground between pure athletic underwear like 360 Sport and everyday underwear like Second Skin.

Buy Now: Shop All Tommy John DriComfort underwear.

DriComfort Underwear Details

• Styles: Boxer briefs only, but available in four-inch, six-inch, and eight-inch inseam lengths.
• Fabric: 72% Nylon and 28% Spandex. 28% Spandex is exceptionally high in men’s underwear, even higher than the 25% Spandex the Air collection has.
• Colors and Patterns: The color selection is minimal, consisting almost entirely of black, dark gray, dark blue, and olive green.
• Price: $36 per pair, regardless of the length you buy.

Final Thoughts on Tommy John Men’s Underwear

From ultra-soft Second Skin to the unbeatable Air trunks and performance-oriented 360 Sport, Tommy John delivers impressive comfort and thoughtful designs. For men who love using the fly, I find Tommy John’s Horizontal Fly design to be the best available. And I am not a fly guy!

Tommy John’s prices are not cheap and you will be spending quite a bit if you wanted to restock your underwear drawer. However, Tommy John has 20-30% sales throughout the year, which are amazing times to stock up. Also, Tommy John gives year-round discounts to government employees, military members, first responders, students, and teachers. If you qualify, take advantage of your discount!

Investing in Tommy John underwear – and at these prices, it’s an investment – is a smart move, especially if comfort, performance, and style are important to you. However, if you are interested in other luxurious men’s underwear, check out my Guide to Mack Weldon Underwear and my Guide to Saxx Underwear.

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