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Escape from underwear hell with this 2021 men's style guide

Are you stuck in underwear hell? Don’t answer too quickly. If you’re wearing the same kind of skivvies you’ve worn since highschool, you could be stuck in a rut without even realizing it. Or maybe you do realize it, and you’re just not sure what to do about it.

The right pair of underwear can keep you comfy, dry, and make you feel great when you look in the mirror. If that doesn’t describe how you feel about your underwear, why not branch out and try something new? Our style guide can point you in the right direction and help you make your way to underwear heaven. 

Here’s what you need to know about the major underwear styles:

Boxer Briefs

Ever since boxer briefs busted the boxers vs briefs debate, they have dominated the top drawer of many men’s dressers. The form fitting undies offer the support of briefs with the coverage of boxers, and the best ones are truly dreamy to wear. Whether you’re stuck on department store packs of boxer briefs or you’ve yet to give this style a try, you're missing out on all they have to offer. 

Tommy John takes on this iconic classic and upgrades the appeal by offering advanced, comfortable fabrics and leg bands that stay in place so you don’t have to make any adjustments throughout the day. Try them in our standard 8” inseam, or choose the mid-length cut if you prefer a little less coverage on your thighs. If you need to boost your support even more, give the hammock pouch a try. It can lift and separate your most sensitive bits to reduce the impact of bouncing, so you stay clean and dry when it’s hot outside. 

If comfort and support are your top priorities - or you simply want to look good in your premium men's underwear - boxer briefs are never a bad choice. 


Trunks offer a more contemporary take on the boxer brief hybrid, offering a little less coverage and the same support as boxer briefs. They work well under short shorts, and they offer most of the same benefits as boxer briefs, although they may not be ideal for people with larger thighs who want more fabric coverage.

If you want to show off the definition in your thighs when you strip down to your skivvies, or you love briefs but want just a little more protection against chafing, trunks may be your new favorite go-to cut. If you incorporate a lot of stretching or lunges into your workouts, or you need to move a lot for work, trunks can offer you a little more freedom of movement than boxer briefs. 


Sure, briefs are typically the first pair of real underwear most little tykes try out, but the right pair can compliment a masculine figure by lengthening your legs and boosting your back side for a more toned look. Briefs have withstood the test of time because they are comfortable and functional, and the minimal fabric can help you stay cool on the hottest of days. 

Tommy John briefs have a fresh look that puts the little boy image of tighty-whities in the rear view mirror. Our classic briefs offer minimal coverage and maximum support, perfect for summertime when you want to sport your shorts. For a more contemporary spin on briefs, our square cut undies offer a little bit more coverage and move the seam away from your crotch for less chafing. 


Since the advent of more contemporary styles and fits, boxers have gotten some undue backlash. They are often paradoxically considered both childish and old man underwear, but Tommy John offers a more contemporary feel with advanced fabrics and a slightly more tailored look. That means you can enjoy the breezy benefits of boxers without looking like you stepped out of a 90s sitcom. 

Boxers work well under relaxed fit denim or on days when you want to chill without feeling constricted. They are also great cool-weather underwear, in case you want to stay warm without committing to full leggings. Even if you prefer having something more form fitting for everyday wear, it’s worth having a pair for lazy days when you don’t want to worry about support. 

The bottom line

No matter what style you feel your best in, you shouldn’t settle for low-quality underwear that itches, bunches, scratches, or doesn’t stay in place. At Tommy John, we’ve developed stunning new styles and advanced fabrics to suit your needs - whether you want to stay cool and dry at the gym or enjoy something soft and silky at the office. 

No matter the cut or fabric you choose, all of our underwear is designed for performance first, which means no adjustments, no wedgies, and no rolling waistbands, no matter how you bend or shift your body. And if you don’t love it, it’s on the house thanks to our Perfect Pair Guarantee