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Beau Hayhoe/Business Insider
When you try on exceptionally well-made pair of underwear after wearing mediocre ones for years, the difference in quality is felt immediately. On the flip side, if you’ve ever worn underwear that doesn’t fit right or breathe well, you know how uncomfortable it can be.
Consider those problems solved by Tommy John , where I’ve been buying my boxer briefs for over 10 years. After testing its fabric technologies across four different styles, I can say that TJ makes the very best underwear for men I own.
Is Tommy John underwear worth $40? In my experience, yes. I wear its Second Skin Boxer Briefs on a daily basis, while the moisture-wicking 360 Sport pair is my favorite for when I plan to break a sweat.
All my Tommy John underwear have retained their shape, the waistbands don’t bunch or stretch, and the fabric doesn’t pill or give way at key stress points (such as around the thighs).
I find myself looking forward to wearing my Second Skin boxer briefs out of anything in my top drawer. They’re smooth, sleek, light, and yet very durable. They fit seamlessly under jeans, chinos or lounge shorts, and there’s no fabric bunching or lingering dampness (we’ve all been there, right?).
How I tested Tommy John underwear
I own eight pairs of Tommy John underwear and tested each one by wearing them from morning to night. Occasionally I’d wear them on long travel days in climates ranging from the brisk autumn of Michigan to the humid heat of Florida.
I considered whether the underwear felt supportive, paying attention to the compression in the waistband, seat, pouch, and thigh areas. I also considered whether they effectively kept me cool and dry as I sweat, and inspected the fabric for pilling, stretching, or fading after I washed them. Learn more about how the Reviews team tests clothing at BI or read our full Tommy John review .
The best Tommy John underwear I tested
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For everyday: The most comfortable boxer briefs overall are the Second Skin Mid-Length Boxer Briefs . I wear these as often as I can. They’re made of super-soft Lenzing Modal (a semi-synthetic, beechwood-derived fiber that’s smoother than regular cotton) with a 10% of Spandex for added stretch.
For exercise: If you need sweatproof underwear, choose the Tommy John 360 Sport Mid-Length Boxer Briefs . The mesh cooling zones offered breathability where I needed it the most, while the fabric is both anti-odor and anti-microbial fabric. I found the curved pouch a sleek, supportive design touch for workouts, and thick waistband means it doesn’t roll down during lunges or squats.
For bedtime: If you’re sensitive to tightness, choose the Second Skin Relaxed Fit Boxers . Whether for sleeping or wearing underneath lounge shorts on relaxed days at home, these boxers blend an easygoing fit with my personal favorite Tommy John fabric, the Modal cotton of the Second Skin line. The contour pouch remains the same, which I personally found highly useful and supportive, while the fit is relaxed at the thigh for mobility.
Tommy John also has trunks (4-inch inseam), square-cut briefs (2-inch inseam), and a mid-length boxer brief (6-inch inseam). There are a vast array of inseam lengths, color combinations and fabric makeups. I’ve also worn Tommy John trunks, which work well with shorts considering their 5-inch inseam.
Tommy John underwear sizing: Does it run small?
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Tommy John underwear does not run small, but it does run long. My usual XL fit me true to size. I wear a size 38 in pants and am typically a size XL in boxer briefs. I felt no constriction in the waist, thighs or seat.
That said, Tommy John’s regular 8-inch inseams are longer compared to other brands. That means its leg bands can reach pretty far down on your thighs depending on your height. I prefer the 6-inch Mid-Length inseams — choose these if you have shorter thighs or need underwear that looks discreet with shorts.
The comfort details set it apart from my Fruit of the Loom underwear.
Tommy John underwear comes with a Hammock Pouch (left) and Quick Draw Fly (right).
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Quick Draw Fly: The Tommy John Quick Draw Fly has a top-down design that offers sleek access without extra fabric bunching up or stretching. A Y-front design, as found in most Hanes or Fruit of the Loom pairs, requires pulling the fly to the side, which is more of a hassle and causes the underwear to lose its shape and support.
Hammock Pouch: This feature costs an extra $2, but it’s worth it. It also delivers much more support than a Y-front design. The pouch integrates easily into the Quick Draw Fly, offering U-shaped support from the bottom upwards. This feature proved extremely helpful for comfortable movement.
A longer inseam and a smooth, wide waistband that stays put all day: Standard underwear that I’ve tried tends to ride up while also not offering as much length and coverage, especially beneath jeans or stretch chinos. Tommy John underwear instead hugs my thighs throughout the inseam. I also loved that the wide waistband didn’t bunch or stretch unnecessarily.
Tommy John has 5 main fabric collections. Here’s how they compare:
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Second Skin (my personal favorite): This four-way stretch blend is perfect for reliable, everyday comfort. It’s made with Lenzing Modal that feels incredibly sleek, smooth and luxurious.
Cool Cotton : These are made of premium, quick-drying Supima cotton with a touch of Spandex for better stretch and shape retention. Supima cotton is usually made of extra long, 1.5-inch staple fibers that make it smoother than the standard 1-inch cotton fiber.
360 Sport : This blend contains 88% polyester and 12% Spandex. The line has designated mesh cooling zones to wick sweat and four-way stretch.
Air : The thinnest of all Tommy John’s fabrics, this 75% polyamide, 25% elastane blend is quick-drying and anti-odor with a tagless label. The Air Trunks work well if you’re wearing tight-fitting pants and don’t want visible seams.
DriComfort (the newest collection): This 72% nylon, 28% Spandex blend feels light and airy, but without any natural fiber content, you do lose some softness.
The bottom line
I wear boxer briefs daily, and after 10 years of wearing its underwear, Tommy John certainly deserves the hype. Once you’ve tried Tommy John’s ultra-soft Modal pairs or incredibly breathable, supportive and durable Supima cotton briefs, I’ve found you’ll recognize an immediate difference in performance and crucial comfort.
Certainly, a higher price tag can be a drawback, so loading up on pairs for every day of the month might prove difficult — but you might find yourself tempted to replace your top drawer with as much Tommy John underwear as it can handle.
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