Fashion Voyeur: Boxers, briefs, boxer-briefs?

Illustration by Maggie Miller Buy this photo

By Max Radwin, Deputy Magazine Editor
Published November 4, 2014

I’m not sure what kind of underwear I’m supposed to buy anymore.

When I was a toddler, briefs were the thing. Then boxer briefs when I grew up a little. Boxers were cool because you were supposed to sag your pants and show them off. I guess it was considered “cool” at the time. I mean I still think boxers are cool — cool enough, or I wouldn’t wear them. I don’t sag my pants like a little hoodlum anymore, though.

My boxers have neat patterns on them, usually. Most of them have a checkered pattern of some kind. But the nice ones have vertical stripes. I can’t explain it, but there’s something classy about vertical stripes. Once my brother asked for silk underwear for Christmas, and they had vertical stripes, too. You can’t get silk underwear in checkered pattern, that’s for damn sure.

Except now, suddenly, all of my friends are wearing boxer briefs. The happy medium between tighty-whities and boxers. Should I also be wearing them? Not that I’m feeling undergarment-related peer pressure, but I’m just wondering if there’s a benefit to boxer briefs. Why the switch, guys? They look too tight, too revealing, too uncomfortable. At the same time, they seem like a more mature type of underwear. It seems like the kind of underwear that a twenty- or thirty-something would wear. In fact, I’m pretty sure that’s the kind of underwear that my dad wears, and he’s fifty-something. The other day I was considering making the change to demonstrate an increased level of maturity. A fake it till you make it kind of thing. But at the same time, I’m content with boxers. They’re comfortable, breezy. I like that. So maybe I’ll stick with them for now.