Why Stylish Guys Everywhere Are Wearing Pajamas in Public
Chalk it up to the pandemic, but wearing your sleeping clothes to have a cocktail is no longer considered slovenly.
BY Demetrius Simms  |  November 29, 2022
4 Minute Read

These days, the only real rule in menswear is that anything goes. Tweens are suiting up, boomers are collecting sneakers, and Brad Pitt recently hit the red carpet in a skirt. And while some of the more outré moves are best left to the professionally bold and beautiful, there is one longstanding fashion taboo worth reconsidering: pajamas in public.

The entry of pj’s into the light of day can be attributed largely to the pandemic. Days, weeks and even months of nearly uninterrupted time at home all but dissolved the line between “house clothes” and clothes-clothes, which gave many a renewed appreciation for finely made loungewear. Elevated pajamas have since turned up at the likes of Valentino and Prada, as well as on the backs of stylish dudes from Florence to Miami. Although conventional thinking might dismiss wearing one’s sleepwear outside the house as slovenly, the key distinction is that this breed of pajamas is intentionally made for sporting en plein air. There’s a big difference between a matched set in crisp piped poplin and the ratty T-shirt and boxers one might typically wear to bed—more Rear Window, less The Big Lebowski. 

“We’ve definitely seen an increase over the last couple of years, as people’s lives have adapted to what’s happening in the world,” says Tom Leeper, creative director of British haberdasher New & Lingwood, the 157-year-old official outfitter to Eton College. “It’s been interesting to think about: What is loungewear? How does it fit into our everyday lives?” One quite literal way of thinking about it, according to Leeper, is that “a pajama top is fundamentally a shirt.”

Indeed, many of the best examples come from traditional shirtmakers such as Turnbull & Asser and Charvet. Piccadilly Arcade stalwart Budd received so many requests for its pajama tops that it began selling them as separates. Andy Poupart, the dandyish software developer behind the Instagram account @StyleAfter50, is a longstanding wearer of Budd’s dress shirts and recently commissioned several bespoke pj tops in washed silk and Solbiati linen.

“I’ve taken to wearing them underneath a double-breasted jacket with the collar outside,” says Poupart, noting that, first and foremost, he’s a fan of the shirts’ roomy cut. But he isn’t drawn solely to their comfort. “I regard it as a lighthearted way of being well-dressed,” he says, describing the look as “consciously subverting the concept of wearing a shirt and jacket.”

Designer Umit Benan, who has included luxurious silk and cashmere pajama sets in every collection since he launched his brand B+ in 2020, agrees that the allure of sleepwear is its balance of rakish nonchalance and tailored refinement. “For me, it’s a styling element that breaks up the seriousness of the classic world,” he says. “I don’t like perfection. I have always liked the idea of being just out of bed but in the streets.”

The look is probably most closely associated with the artist Julian Schnabel, who has made a uniform out of full pajama sets topped with a sport coat. Not that one must go full Schnabel; for those who feel exposed venturing out in such intimate apparel, Leeper suggests that “transitioning from a conventional shirt to a pajama shirt under a blazer is an easy, small step to taking sleepwear outside.”

In fact, assigning the pj top to daytime duty is actually bringing the garment full circle, according to Harri Cherkoori, of Viennese pj’s specialist P. Le Moult. “Pajamas started as daywear,” he says, noting that “British officers posted to India had originally taken up wearing local pajamas in blistering heat.” It was only after an official directive forbidding the British military from adopting local customs that pajamas—derived from the Urdu-Persian pai jamah, meaning “loose leg garment”—were relegated to domestic life. “The ‘traditional’ shirt is now worn by people working in the service industry, be they blue-, white- or gilt-collar jobs,” Cherkoori says, predicting that, as the look of distinction evolves, “the new, younger captains of industry will be wearing nontraditional shirts.” So while pajamas may still raise eyebrows in the boardroom, they certainly deserve a place beyond the bedroom.