• Newsletters
  • Subscribe
/
1x
Fashion

18 Ways To Master Pajama Dressing For Your Next Holiday Party

What could be better than spending the night dressed in silky satin and luxe velvet?
By Caitlan Moneta
Add as preferred on Google(opens in a new tab)
Addition Elle L&L Embroidered Kimono

After years of fitted dresses and stilettos, the fashion gods have turned the tables. Comfort is (finally!) the name of the game. Slipper-like slides, slinky slip dresses and, best of all, pajama dressing are the chicest ways to dress up (or rather, down) for party season.

But these aren’t your old flannels or your boyfriend’s tees. We’re talking about glamorous buttoned or wrap tops and flowy pants that are meant to be seen outside of the bedroom. Not bold enough to try a full printed set in silk or velvet? Try just the top with a pair of classic cigarette pants, or the pj-inspired pants with a cozy cashmere sweater.

Shop the dreamiest pajama looks below.

Pyjama Dressing

Joe Fresh

Piped Lace Shirt, $20, joefresh.com. Piped Jogger, $25, joefresh.com.

Advertisement
Joe Fresh Piped Lace Shirt and Piped Jogger

H&M

Patterned Shirt, $70, hm.com. Wide-Cut Pull-On Pants, $35, hm.com.

H&M Patterned Shirt and Pants

Addition Elle

L&L Embroidered Kimono, $85, additionelle.com. L&L Printed Wide-Leg Satin Pant, $50, additionelle.com

Related Stories

The 4-in-1 Bikini Top For All Your Summer Plans
Sponsored

The 4-in-1 Bikini Top For All Your Summer Plans

From the pool to the patio, this convertible swimsuit works wherever the day takes you.
Addition Elle L&L Embroidered Kimono

Zara

Pyjama Shirt, $70, zara.com. Printed Trousers, $70, zara.com

Advertisement
Zara Pyjama Shirt and Printed Trousers

Banana Republic

Stripe Pajama-Style Shirt with Piping, $110, bananarepublic.ca

Banana Republic Stripe Pajama-Style Shirt with Piping

Banana Republic

Avery Ankle-Fit Stripe Pants, $124, bananarepublic.ca

Banana Republic Avery Ankle-Fit Stripe Pants

Ann Taylor

Belted Velvet Blazer, $240, anntaylor.com. Velvet Smoking Pants, $160, anntaylor.com

Ann Taylor Belted Velvet Blazer and Velvet Smoking Pants

J.Crew

Pajama Top in Ratti Paisley Floral, $168, jcrew.com. and Collection Pajama Pant in Ratti Floral Print, $259, jcrew.com

Advertisement

J.Crew, Pajama top in Ratti paisley floral, $168,

J.Crew, C $259,

J.Crew Pajama Top in Ratti Paisley Floral and Pants

Forever 21

Plus Size Satin Floral Pajama-Inspired Shirt, $38, forever21.com

Forever 21 Plus Size Satin Floral Pajama-Inspired Shirt

Free People

So SO Chic Romper, $164, freepeople.com

Advertisement
Free People Romper

H&M

Jacquard-Weave Jacket, $99, hm.com. Jacquard-Weave Pants, $70, hm.com

H&M Jacquard-Weave Suit

Boohoo Plus

Kerry Oriental Print Blazer, $70, boohoo.com

Boohoo Plus Kerry Oriental Print Blazer

Boohoo Plus

Lisa Oriental Floral Print Woven Trousers, $57, boohoo.com

Boohoo Plus Lisa Oriental Floral Print Woven Trousers

Mango

Floral Print Shirt, $70, mango.com. Floral Print Trousers, $70, mango.com

Advertisement
Mango Floral Print Shirt and Trousers

Topshop Lips Print Pyjama Jumpsuit

Lips Print Pyjama Jumpsuit, $128, topshop.com 

Topshop Lips Print Pyjama Jumpsuit

Zara

Velvet Shirt with Fringe, $129, zara.com. Velvet Culottes, $50, zara.com

Zara Velvet Shirt with Fringe and Culottes

Scotch and Soda

Velvet Suit, $443, freepeople.com

Free People Scotch and Soda Velvet Suit

Elise

Stormy Ocean Camellia Silk Pajamas, $347, wearelise.com.

Advertisement
Elise Stormy Ocean Camellia Silk Pajamas

Watch: The easy way to get a sculpted brow

The very best of Chatelaine straight to your inbox.

By signing up, you agree to our terms of use and privacy policy. You may unsubscribe at any time.
Advertisement
Advertisement
Copy link

More Like This

Chatelaine Summer 2026 cover, featuring a woman biting into a burger.

Subscribe to Chatelaine!

Sandwiches! Sundaes! Jello shots! Plus the lowdown on the female desire pill, women who hit major life milestones at 50 and guest editor Meredith Shaw's all-Canadian summer lookbook.