In retrospect, I should have learned something from a puberty spent ogling models in the Victoria’s Secret catalog: All that fancy, sumptuous and seductive lingerie is designed for men. This is the stuff of naughty Valentine’s Day surprises, of attempts to “spice things up in the bedroom” or simply divert attention from an ongoing Netflix binge. I’m not saying women never wear it for their own reasons, but it took forever to realize that male expectations may drive women’s desire to feel dressed up when getting naked.
First off, thanks for going through all the trouble; you look fantastic. Secondly, I’m sorry I haven’t returned the favor. Not long ago, in a MEL writers’ meeting, I broached the issue of how dudes select their underwear on a day they anticipate some action down there. In my 30-something naiveté, I figured we’d be talking about the ideal textures and patterns, and even superstitions — a “lucky” pair, perhaps — only to discover I had stepped on a sartorial land mine. Everyone was appalled to learn that I wore boxers.
https://twitter.com/MilesKlee/status/941010539500597248
https://twitter.com/MilesKlee/status/941019633536057344
https://twitter.com/MilesKlee/status/941020078304137216
The burns came down with fire and fury: Boxers are for teens and other pimply, Mountain Dew-chugging gamers. Boxers are as close as you can get to wearing diapers. Boxers make your ass look like a shapeless wet grocery bag in a street gutter. Some people privately DMed to say that boxers were fine, but nobody really liked them. The best you could say about boxers was that there might be a good dick inside them.
https://twitter.com/patricknathan/status/941012736632377344
The same consensus that condemned boxers saw fit to elevate the sleekest hybrid alternative: boxer-briefs. To the best of my recollection, I’d had exactly one pair of these in my life, solid black and awkwardly stark on my scrawny pale frame. They were probably a size or two larger than they should’ve been, failing to support my junk or define my butt, as boxer-brief evangelists insisted a decent pair would. In the decade since those had left my undergarment rotation, I’d experimented with brightly colored briefs and encountered the opposite problem: These inevitably rode up, gave me weird wedgies, and were tight enough to cause rogue boners at the drop of a hat.
Given these experiences, I’d capitulated to the idea of boxers as the lesser of three evils — not in any way commendable, though you could get a passably cute pair at Uniqlo. But a real man is willing to admit his mistakes, and that’s why I made the even greater mistake of venturing out to the Santa Monica Promenade a week before Christmas to find the boxer-briefs that would change my entire worldview. Deeply intimidated by the combination of harried shoppers, aggressive salespeople, and a giant cutout of a sculpted adonis in boxer-briefs outside Calvin Klein, I took refuge in the relatively low-stakes H&M, where I picked out three sets of trunks in a range of blues and grays. With these colors, and one anchor-patterned selection, my tastes leaned toward “sailor on shore leave” — far better than Urban Outfitters’ garish vaporwave vibes.
Anyway, I have enough shame not to include a photo of myself in the boxer-briefs I did buy, so for the sake of illustration and my ego, let’s pretend they looked like this on me:
My first impressions were overwhelmingly positive. I did enjoy having a snug bulge and a tightened-up ass. Madeline, my girlfriend, approved as well, despite earlier assurances that she’d never been turned off by my boxers — made out of pity, I suspect. Yet the greatest advantage I discovered in boxer-briefs had nothing to do with packaging myself as a sex object: Where boxers bunch up under your jeans, form-fitting boxer-briefs turn walking into a mostly frictionless activity. And despite concerns that I’d be sacrificing breathability, crotch and taint sweat remained at tolerable levels. As with briefs, I did note some riding and unexpected hard-ons, though the boxer-brief form was clearly better equipped to restrain the latter in a comfortable way. I was a convert.
when you’re hot no one cares what you’re wearing but aren’t boxers uncomfortable like you’re wearing shorts under your pants?
— your own personal jesus (@Kappa_Kappa) December 13, 2017
you're basically wearing a bathing suit under your pants and i respect that
— matt▲lubchansky (@Lubchansky) December 13, 2017
https://twitter.com/johnwilmeswords/status/941177757047906304
After this awakening, when I visited home for the holidays, I came to understand how the evolution of my underwear drawer had gone awry. Each Christmas Eve, my mom gives me and my brother and sister “pajamas” — which for the last couple decades, for the boys, meant boxers and a T-shirt. When the gift bags came out this year, I mentioned that I’d taken a liking to boxer-briefs and asked my dear mother how she’d come up with the boxers tradition. Ignoring my dad’s canny warnings that I was just going to put whatever she said in an article, she repeated several times that she’d considered boxers “sexy” ever since persuading my father to switch from the dreaded, threadbare, stained tighty-whities he’d worn when they first met.
It was sweet, in a way, that she wanted her sons to live up to her own ideal of masculine semi-nudity, yet if anything was a final strike against boxers for me, it was that startling confession. Already the boxer-briefs have become my preference; I suspect they’ll soon be my only option in gearing up to face the world.
Just the same, there will always be a place in my heart for boxers. They were there for those first fumbling hookups and throughout my marriage (I’m 80 percent sure they aren’t the reason I got divorced). They slid off easily when it was time to go streaking in college, and they served as impromptu bathing suits in a pinch. On a sick day, or some lazy weekend I feel like wasting on the couch, eating messily from a party-size bag of chips, they will serve as the flabby house shorts I need to keep crumbs out of my pubes. And I refuse to denounce any man who prefers them to boxer-briefs in any context. All I would tell them is this: The world is full of solutions to problems we don’t know we have.
Miles Klee
Miles Klee is MEL’s resident tank-top dirtbag, shitposter and meme expert. He’s also the author of the novel ‘Ivyland’ and a story collection, ‘True False.’
