Tommy John Men’s Underwear: A Comprehensive Guide

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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.

Overview of Tommy John Men’s Underwear

I own four 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, and one pair of Air four-inch boxer briefs. I am happy with all four pairs. However, since I am not a boxer shorts guy, I don’t wear my Second Skin boxer shorts much at all.

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.

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 three Tommy John lines pass this test: Second Skin, 360 Sport, 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.

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.)
• 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 three: Second Skin, 360 Sport, and Air. Those three, along with Cool Cotton, comprise the bulk of Tommy John’s underwear lineup. The fifth collection – Apollo – has fewer styles and colors. Tommy John looks to be phasing out Apollo underwear as it is no longer listed as a featured Collection on their website.

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).

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 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.
• 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.

Last update on 2025-07-16 at 13:46 / Affiliate links / Images from Amazon Product Advertising API

• Customer Reviews: I have summarized the customer reviews of Second Skin from Tommy John’s website: Second Skin is the most popular Tommy John line, and customer feedback frequently highlights its supreme softness and comfort, often saying it “feels like you’re wearing nothing at all.” Customers love the smooth non-pilling fabric that stays comfortable even after many washes. The fit is noted to be snug but true-to-size with ample stretch, preventing riding up or bunching during the day. Many customers mention Second Skin as their go-to daily underwear for work, travel, and even sleeping, thanks to its barely-there feel and supportive 4-way stretch. One common contrast in feedback is that men who “run hot” or sweat a lot sometimes prefer Tommy John’s cotton or mesh options (Air) for the coolest feel – Second Skin is breathable, but some users in very hot climates find Cool Cotton or Air more suitable for heavy sweat. Overall, however, Second Skin earns consistently high praise for its softness, light weight, and all-day comfort, making it a top-rated essential in Tommy John’s lineup (over 9,000 reviews with an average of ~4.7★)

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

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. However, 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. But compared to Under Armour, Tommy John’s 360 Sport is only marginally better in my opinion. 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.

360 Sport Details

• Styles: 4-inch, 6-inch, and 8-inch boxer briefs. No briefs, sorry.
• 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.
• 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.

Last update on 2025-07-16 at 08:57 / Affiliate links / Images from Amazon Product Advertising API

• Customer Reviews: Here is a summary of customer reviews of the 360 Sport line: Generally, this line earns high marks from customers. Reviewers frequently praise the supportive fit and report that these boxer briefs stay in place during workouts (no chafing or ride-up, even through squats or running). The mesh cooling zones receive special mention: customers appreciate the targeted ventilation, which keeps them cooler and prevents sweat buildup in key areas. Many reviews highlight that the fabric is fast-drying and lightweight, ideal for gym sessions or sports. Another recurring praise is the odor control – users note that even after intense exercise, the underwear resists odors (thanks to the anti-microbial treatment) so they “don’t stink up the gym bag.” In terms of sizing, most find it true-to-size with a compressive, athletic cut (some size up for a bit less compression, but overall the fit is as expected for performance wear). Complaints are uncommon; a few reviewers mention they’d like more color choices or miss the days when a side pocket was included, but these are minor points. In summary, the 360 Sport line is widely praised by runners, weightlifters, and active guys for its combination of stretch, support, cooling, and odor-free comfort.

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

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Air Collection

My absolute favorite Tommy John underwear line is the Air collection, specifically the 4-inch inseam trunks. 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 stylish and fit perfectly, offering just the right amount of support without being restrictive. And they look fantastic!

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.

Last update on 2025-07-16 at 09:11 / Affiliate links / Images from Amazon Product Advertising API

• 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.
• Customer Reviews: The general consensus is that devoted fans of Air underwear use it for travel and summer wear. Common feedback highlights how incredibly light and breathable the material is – many describe it as “the next best thing to wearing nothing” in terms of comfort. For example, customers report wearing Air boxer briefs on long flights or hikes and remark that they stay cool and dry, where ordinary cotton underwear would have been soaked. The quick-dry nature is a big hit with travelers: numerous reviews mention washing a pair in a hotel sink and finding it ready to wear the next morning, saving space in the luggage. In hot and humid climates, Air briefs get praise for preventing that sticky, clammy feeling. The fit is described as slightly more sheer and less compressive than other lines, but still supportive enough – a few reviewers note that because the fabric is so thin, you should be a bit careful pulling them on (to avoid overstretching or snagging the mesh). Durability is generally good, given the material (most are surprised at how well such a lightweight fabric holds up), but gentle care is advised (I always recommend air-drying men’s underwear). Overall, the Air collection garners strong reviews (~4.6–4.8★ average on various Air styles) for delivering on its promise of ultra-light, breathable comfort, especially from customers who use them for travel, outdoor adventures, or brutally hot weather.

See More: Tommy John Air Briefs.

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. Although I haven’t personally tested Cool Cotton underwear (I don’t like cotton underwear), customer reviews highlight their exceptional comfort, particularly for everyday wear.

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.

Last update on 2025-07-16 at 12:17 / Affiliate links / Images from Amazon Product Advertising API

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 boxer briefs to boxer shorts.
• 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.
• Customer Reviews: Here is the summary: Men who wear the Cool Cotton line often comment on how well it keeps them cool and dry, echoing Tommy John’s claims. Many reviews come from customers in warm climates or those with jobs involving physical activity – they praise the breathable Supima cotton fabric for “natural sweat control”, saying it evaporates moisture faster than their old all-cotton underwear. A recurring theme is that Cool Cotton underwear is comfortable for men who tend to run hot. Guys mention staying comfortable “even on humid summer days” in these. The fit and construction get positive notes similar to Second Skin (no riding up, a soft waistband that doesn’t pinch or roll). In side-by-side comparisons, some customers acknowledge Cool Cotton isn’t quite as silky-soft as the Second Skin modal fabric, but they still rate it highly because it “breathes” better for workouts and hot weather. Overall, reviews (many thousands, averaging ~4.6★) indicate high satisfaction, especially from those who value a cotton feel with performance moisture-wicking. Any complaints are rare, typically from users who expected the same silkiness as modal – but most agree that the comfort and cooling of this line make it ideal for everyday wear and exercise.

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

Apollo Collection

Apollo underwear is a newer underwear lineup featuring 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 (79% 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.

Last update on 2025-07-16 at 09:26 / Affiliate links / Images from Amazon Product Advertising API

Apollo Underwear Details

• Styles: Boxer briefs only, but available in four-inch, six-inch, and eight-inch inseam lengths.
• Fabric: “drirelease” fabric with a blend of 79% polyester, 14% modal, 7% Spandex. It is an interesting material combination, especially with a Spandex content of less than 10%. I feel that 10% Spandex or higher is essential for ultimate flexibility and comfort.
• Colors and Patterns: The color selection is minimal, consisting almost entirely of black, dark gray, and dark blue. Apollo waistbands have a special “TJ” logo design not found on other Tommy John underwear.
• Price: $36 per pair, regardless of the length you buy.
• Customer Reviews: Customer reviews frequently comment that Apollo fabric is soft and smooth against the skin – many are surprised that a predominantly polyester blend can feel so luxurious, but the addition of Modal lends it a cotton-like softness. Another theme in feedback is the noticeable cooling effect – users in warm climates or those who run hot mention that Apollo underwear indeed keeps them cooler and drier than regular cotton boxers, validating the ‘cooler than cotton’ claim in real-world use. They also love how quickly these dry; some have worn them for exercise and found that sweat dries up fast, preventing that damp feeling during the day. Many reviews describe Apollo as their “do-it-all” underwear – equally comfortable at the office, on the go, or at the gym. In terms of fit, Apollo is described as form-fitting (similar to Second Skin) and true-to-size; the stretch fabric accommodates movement well. A few users mention the waistband on this line is slightly wider and very secure (no rolling). There are few complaints so far – a minor one from some was the price point, but even those reviewers often add that the performance makes it “worth it.”

See More: Tommy John’s Apollo men’s underwear.

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 (you can email me if you want me to alert you when there are sales). 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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