Our editors independently select the products we recommend. We may earn a commission on items bought through our links.
Stephen Powell grew up in a small town in Mississippi. He was always detail oriented, smart, and choose-y. He chose to become a physician. He chose to wear nicely tailored suits. He chose to present himself in a certain way – immaculate button downs, tailored jackets. But something nagged at him. A few things actually: lyocell, modal, and elastane. He hated his boxer briefs.
Today's Top Deals
“Made in America” is generally a good thing – a bit of patriotic reassurance and a sign of quality. But that’s not precisely the case when it comes to men’s underwear. Most large American brands traffic in the synthetics that bothered Powell. Good for beating swamp ass; bad for feeling confident. A handful of brands across the pond, notably the British brands Sunspel and Hamilton & Hare and the Swedish brand CDLP, produce a more thoughtfully constructed product, but stateside that space remains freshly wandered white.
So Powell made a rather eccentric choice. He started an underwear line. You treat the patient in front of you.
“I like to think we are selling much more than just underwear here,” Powell says. “It’s an aspiration to a life well and authentically lived.”
Powell talks about underwear the way Wim Hof guys talk about cold plunges and capitalism’s street preachers talk about passive income. He bemoans “all of these ‘ball pouches‘” and appears to genuinely believe that his Italian-made briefs, boxers, socks, and undershirts, which have a fuller cut that gives them a Gary Cooper vibe, are the prescription for what ails the modern man: the sort of malaise that comes from being gently cupped by lycra. Powell talks a lot about character.
The language Powell employs – “We strive to inspire men to achieve, provide, and take true action in their lives centered with wholesome character” – is what gives away the project. It’s abstract. It’s, as they say in Mississippi, high falutin’. It’s not just the sort of language one employs when selling $38 boxer briefs; it’s the poetry of lingerie. Powell is putting a masculine twist on the only-I-know-about-my-lacy-undies frisson of Agent Provocateur. Like that (wonderful) brand, Powell is ultimately in the confidence business. He makes job interview underwear. He makes date night underwear.
“Imagine a man in a made-to-measure suit, yet underneath are tacky, overly patterned and unnecessarily ‘technical’ underwear,” says Powell. He sounds like he’s describing a pathology.
Classic Fella isn’t the only brand in the men’s lingerie game. Fleur de Mal, which makes popular bralettes, also sells lacy boxer briefs. So does Menagerie, though the name is probably disqualifying. The difference is that both of those brands seem to have forgotten Victoria’s Secret, which is that underwear is about the person wearing it, not the person taking it off. There’s a market for sex stuff – always, always – but the market for a confidence boost is bigger.
Is men’s lingerie about to take off? Sales trends don’t tell that story. They do, however, support the idea that men are willing to pay more for better and that there is demand – real demand, sustained demand – for something that feels just a bit special.
Classic Fella Classic Boxer Briefs
More Top Deals from SPY
Best of SPY