‘Pajama Dressing’ Is Always a Good Idea

Sometimes, trends can feel stressful. You might think, I have to buy something new, again? Or, Everyone is wearing this new thing and it’s cute but it wouldn’t suit me. We get it. But there truly is something for everyone when it comes to one of our favorite trends from this season: pajama dressing. Whether you choose to commit to a full look or just dabble in the trend, you’ll find something to love about this cozy fashion moment.

The PJs-as-clothes trend has been embraced by celebs including Salma Hayek, Zendaya, Selena Gomez, and Victoria Beckham. Celebs are often seen dressing up the casual look by adding stilettos or punchy, impactful jewelry. You can go dressy or casual with this trend, which is why it’s so versatile for all styles and ages. Keep reading for our favorite ways to get the look.

What Is Pajama Dressing?

Pajama dressing is pretty much what it sounds like — wearing pajama-like clothes often designed as streetwear (though you also could shop the men’s PJ department to get the look). The general vibe is casual and relaxed, but silk pajamas make for an untraditional dressed-up look, too. Look at how creator Judith Boyd wore a printed set with black strappy heels and a sophisticated hat. Or how artist Victoria Nuguid embraced mixing prints and textures. The styling options are truly unlimited.

How To Wear Pajamas in Real Life

Say you go for a full pajama outfit with a matching set (another current trend). The best way to elevate the look is with accessories. We’re talking structured shoes (sneakers, loafers, or even heels), a full stack of necklaces, and maybe even a blazer, as an extra visual cue that your pajama dressing is totally intentional.

If a matching set is a little too much for you, play around with separates. Add striped pajama shorts (and sneakers) to your sweater set, or pair wide-leg silk pants with a white button-up shirt and slingbacks to get a similar, laid-back vibe that’s a bit more wearable for everyday.  

Shop the trend:

1. Sleeper Cha-Cha Linen Lounge Set in Navy

Grabbing a set from Sleeper has to be the easiest way to get into pajama dressing, because the brand makes “sleepwear” you can wear in real life. We love this linen set you can wear together or with other separates in your closet.  

2. Free People Get Free Striped Pull-On Shorts

These boxer-inspired shorts, with their fun blue and red stripes, do the heavy lifting on your outfit for you, so the rest of your styling can be as simple as a solid black or white T-shirt. Alternatively, you can add a sultry spin on a masculine-inspired look with a crop top.

3. Parke Eyelet Boxer Pants

Another way to put a feminine spin on a masculine, casual trend? By rendering it in the cutest fabric ever — eyelet. These easy, pull-on pants are comfy but still so chic for warmer weather.

4. Never Fully Dressed Shells Miley Shirt With Gold Fleck and Elissa Trousers

This dressed-up pajama set could even be worn to a fancy event with strappy sandals and leather accessories. We love the wearable white shirt with blouson sleeves and a floaty silhouette, plus the easy pull-on pants that match. 

5. The Great The Boxer Shorts

These leopard boxers are a splurge, to be sure, but the untraditional pattern puts such a fun spin on the pajama-dressing trend. No one will think you pulled these out of your boyfriend’s underwear drawer.

6. J.Crew Cotton Poplin Boxer Short Set in Stripe

Technically, this matching set is pajamas, but it’s just begging to be worn in the real world. J.Crew even made a “sleep bra” to complete the set and ensure you’re both comfortable and supported. The mix-and-match possibilities are endless.

7. Alémais Lemonis Wide Leg Silk Pants

When it comes to pajama dressing, you’ll see a lot of basic patterns like stripes — and we love love stripes. But it’s fun to mix things up with something truly fabulous and splurge-worthy, like these fruit-emblazoned pants you can dress up or down.

8. Alex Mill Poolside Shorts in Positano Stripe

These striped boxer-inspired shorts come in three cute colors — and if you’re feeling the ease of matching sets for summer, you can get the corresponding button-down top, too.