The Key to Easy, Elegant Outfits Might Have Been Hiding in the Men's Department All Along

Brie Welch is a Who What Wear editor in residence. In addition to being Katie Holmes's longtime stylist, Welch is a costume designer and eBay's resident stylist. This role includes curating eBay Watchlist, a quarterly trend report powered by shopper data. She resides in New York City.

While in Paris a few summers ago, I found a beautiful set of men's paisley-print silk-flannel pajamas at a vintage store in the 10th arrondissement. It was unexpected given the outside temperature and the more seasonally appropriate piece I bought with it, a fitted Dolce Gabbana silk minidress. Life is full of contradictions! Surely, our closets are the greatest examples of this, especially when items that are normally reserved for sleeping make their way to the streets.

Case in point: the classic pajama set, a time-honored gift for men during the holiday season that's snuck its way into the depths of my brain and created a myriad of everyday outfit ideas. Apparently, I'm not alone. On eBay, searches for silk pajama sets are up 34%, according to the company's just-released trend report, eBay Watchlist, which is based on global eBay search, sale, and listing data collected between August 2024 and August 2025.

When I think of men's pajamas, I always conjure up images of Audrey Hepburn in Roman Holiday when she dons Gregory Peck's striped pj's. She emanates girlishness while daring you to think the menswear staple would make a great top. It's very Prada F/W 25 when worn with a more feminine flair, like a pencil skirt or miniskirt and ladylike shoes. I think that the idea of rolling out of bed and onto the sidewalk with little heels and a bag is the ultimate sophistication.

I'm reminded, too, of Carrie Bradshaw in Sex and the City on New Year's Eve when she ventures out into the perilous snowy subway in her lightly patterned pajama pants, which were worn with heels, a voluminous fur coat, and a little sequin cap. How chic! It's also very Chloe King—she could pull off that whole look and inspire a slew of iterations.

Bringing it back to the pajama set, these are best suited to stripes and patterns and being worn separately in these non-bed situations. For men too, I'd be keen to see silk pajama bottoms or even designer printed silk pants (eBay searches for Gucci silk pants are up 59%, by the way) worn with a cashmere sweater, chunky socks, and loafers out to coffee. The look is casual but has more intrigue than sweatpants, like if Gene Kelly played The Dude instead of Jeff Bridges.

Tips

1. Size Up
Buy a larger size than normal. This allows you to play with proportions and shift perception away from the origins.

2. No Piped Cuffs
Look for sets where the pants specifically don't have piped cuffs. They err more on the pajama side of life.

3. Avoid Prints
Stay away from kitschy prints and stick to solids, stripes, and paisleys in rich colorways.

I think the key to trying this out on your own is balance—even Sofia Coppola at the Met Gala understood that, as a stand-alone look, they can't be your average cotton pj's. There's gotta be pizzazz. It's about mixing pajamas with traditional ready-to-wear pieces to create interest. Think classic tailoring, luxurious knits, and unexpected footwear, like metallic sneakers, kitten heels, and penny loafers.

Pajama shirts as button-downs are not so far-fetched either. Why not give them a try?! Without further ado, get scrolling to start styling your pajamas for more than just sleeping.

Designer Pajamas

Vintage Pajamas

Pajama Styling: Shoes

Pajama Styling: Knitwear