What a Man's Underwear Choice Says: 5 Semi-True, Funny Snap Judgments

1. A man in baggy boxers is all about comfort.

All the rage in the 1990s, loose-fitting boxer shorts used to be seen as a more manly alternative to briefs, whose snug, earnest, boyish practicality contrasted with the street style of the day, saggy jeans. Roomy boxers were the coordinating fashion choice for oversized, low-slung jeans that put men’s underwear on display like never before. 

While sensible briefs were what your mom probably bought you in elementary school, boxers were what you bought yourself as soon as you could to avoid social shame from high school onward. 

The problem is that cheaply-made 90s boxers were never all that comfortable. They bunched up in the back and around the legs, interfering with the look of slimmer-fitting pants, and with the comfort and dignity of the wearer. (No man looks good readjusting his drawers all the time). They obscured the shape of the body beneath, suggesting the wearer either lacks confidence or isn’t at all concerned how he presents himself in pantsless situations. 

Fortunately, if you prefer boxers, you’re no longer stuck with baggy or poorly-fitted brands. Tommy John reinvented boxer shorts with a contoured pouch that gives you support and a non-roll waistband so they stay put. The comfy underwear choice is more comfortable than ever.

2. A man with printed underwear has serious confidence.

The 1990s boxer short trend did contribute a renewed appreciation for creative colors and prints in men’s underwear. Novelty prints meant to be seen in public above saggy waistbands brought a sense of rebellious fun back back to men’s underwear. 

Today’s patterns and prints are more refined. They’re less about rebellion and novelty and more about sophisticated self-expression. A grown man should have more options in his underwear than white, black and cartoon characters, reflecting the complexity and refinement of his personality. Humor has its place, but your underwear prints, like your dinner conversation, should be less immature jest and more knowing wink. 

A man who dons underwear in a handsome seasonal print or assertive color block knows who he is, what he deserves, and what he wants to say. He is ready for his day and whatever it brings, and will greet it with the full force of his intellect, character and style.

3. A man in antique tighty whities is old-fashioned (or completely oblivious).

Old-fashioned, poorly-fitting, squeeze-you-to-death tighty whities are a strange fashion choice indeed. What kind of men would wear them?

Two possible reasons: here is a man who knows his preferences and has no intention of changing. No matter how uncomfortable or goofy his briefs look, he’s going to keep buying the same brand he wore as a child. Alternately, a man in white briefs is simply clueless. Perhaps he has never heard the phrase “tighty whities.” The reasons for his oblivion are fascinating… but perhaps unknowable.

Either way, the important thing to know is that briefs have come a long, long way in the last few decades. With Tommy John’s briefs, all of the aforementioned tight-whitey problems (style, fit, comfort) have been completely solved. 

4. A man in boxer briefs is ready for anything.

Boxer briefs are the go-to underwear for the modern man. They are practical and attractive, accommodating to active lifestyles and athletic silhouettes. They provide support and comfort and rarely get in the way. 

Patterns and prints allow for personal expression, but the boxer brief itself says: “I’m a solid, sane, stand-up guy. I want to look good, feel comfortable and be ready for any situation, without a lot of fuss. I care how people see me, but I don’t let fashion trends get in the way of what works.”

With extended thigh coverage and a body-hugging fit, boxer briefs strike a perfect balance when it comes to intimate style. They are no-nonsense, suggestive to the imagination without being overly revealing. They say “I’m not showing off here,” while also asserting “I’ve got nothing to hide.” 

A man in boxer briefs has a lot more going on in his life than his underwear, but he expects his clothing to serve his needs, support his lifestyle, and help him be his best self every day. 

5. A man in trunks has great thighs.

Trunks and other shorter-cut takes on the boxer-brief provide the same benefits of comfort and support that boxer-briefs do, while baring a bit more skin. 

Some men opt for less thigh coverage to stay cool or to avoid fabric riding up uncomfortably. (Important note: while this is an issue with some lesser brands, all Tommy John underwear is designed first and foremost to stay in place, so we guarantee you won’t have this problem with our next-level boxer-briefs). 

But some men just have great-looking thighs and know it, and we think that’s reason enough to show a little more skin. Few things build confidence like knowing you look good and dressing accordingly. A man who wear trunks, square cuts, or even briefs has a great feature he isn’t afraid to flaunt. Nothing looks better on anyone than that kind of fearless confidence.