Pajama Dressing 101: Sleepwear Styling at Its Finest

Pajama Dressing 101 Sleepwear Styling at Its Finest

The fashion world has long embraced pajama dressing—from the latest street style, where showgoers donned Prada’s piped cotton separates, to our favorite celebs (Rihanna and Jennifer Lawrence recently sported matching sets), it’s an effortless look with cinematic flair. In fact, some of our favorite women on the silver screen—from Audrey Hepburn in Breakfast at Tiffanys to Lauren Bacall in The Big Sleep—blurred the lines between sleepwear and personal style.

Vogue’s Guide to Pajama Dressing

The Pajama Shirt
Prada cotton shirt
Jump to review
The Boxer Pant
Comme Si La Boxer Alta
Jump to review
The Mule
Ancient Greek Sandals The Slipper satin mules
Jump to review

References to the master bedroom inspired many of the spring 2026 shows, too proving the fall fashion trend will carry over into next season. Erdem, notably, styled a striped and sequin set with a collarless coat, flower brooch, and statement floral heels. Max Mara, meanwhile, paired its silk printed set with a belt and plush scarf for a jumpsuit effect. Valentino reimagined the silk and piped shirt as a jacket over a dress.

When it comes to wearing these pieces out, it’s about being intentional without trying too hard. Pair a silk top with denim; layer a trench coat over a lace-trimmed house dress, or throw a chunky knit over crisp cotton PJ bottoms. For a more one-and-done approach, turn to brands like Olivia Von Halle and Sleeper—their fancy pajama sets are elevated enough to wear out of the house as-is (with the right accessories, of course).

Ready to revamp your loungewear? Our guide below will help you embrace pajama styling at its finest.

Pajama Top + Corduroy Trousers + Leopard Bag

Take a pink and brown color combination for a spin with Prada’s sleepwear-inspired top and a pair of Polo corduroy trousers. Ground the duo with Le Monde Beryl’s white Mary Janes then add graphic punch with Toteme’s leopard-print bag. Top off with silver earrings and croc-embossed belt.

Prada

cotton shirt

Polo Ralph Lauren

wide-leg pants

Le Monde Beryl

Mary Jane flats

Lady Grey

Scala huggie hoop earrings

Rag Bone

Audrey belt

Toteme

T-lock calf hair clutch

Cashmere Knit + Boxer Pants + Trench Coat

For an easy look that will make you feel polished and while feeling like you never left the comfort of your home, take Comme Si’s striped boxer trousers for a spin. Style with a white tee as your base and a V-neck knit on top, plus a trench coat to shield you from any inclement weather. Accessorize with a cord necklace and Prada nylon pouch—a coveted runway find that likely won’t be around for long.

Ysso

sterling silver and cord necklace

Comme Si

La Boxer Alta

&Daughter

Balla wool sweater

Éterne

boyfriend T-shirt

Prada

re-nylon pouch

The Frankie Shop

Bleecker trench coat

Striped Set + Collarless Coat + Brooch

For an easy outift, try Róhe’s sleepwear-inspired set with a sleek collarless coat. Pair with burgundy loafers for a subtle pop of color, and accent with unexpected jewelry extras—a silver brooch and hair pin.

Róhe

oversized silk shirt

Róhe

silk wide-leg pants

Zara

wool blend coat

Vivianna Torun

brooch

Lié Studio

The Frida hair pin

Mansur Gavriel

penny loafers

Piped Shirt + Fringed Midi + Suede Loafers

Juxtapose the playfulness of Dries Van Noten’s fringe skirt with Tekla’s piped blue pajama shirt. Artfully wrap a grey knit at your waist, then anchor the pairing with boat shoes for a cheeky wink. Blue-tinted sunglasses, and an initial necklace end the look on a statement-making note.

Tekla

long-sleeved shirt

Dries Van Noten

fringed midi skirt

Black Suede Studio

Davy suede loafers

Jacques Marie Mage

Zephirin 47 sunglasses

Alex Mill

Nottinghill sweater

Brilliant Earth

Wavelength initial pendant

Mixed Print Set + Shearling Coat

Lean into the boho revival with a paisley printed pajama for a ’60s moment, finished with heeled mules, statement earrings, and a shaggy black shearling topper.

Zara

paisley pajama shirt

Zara

paisley pajama pants

Loewe

leather mules

Jil Sander

Cannolo shoulder bag

Juju Vera

Eliza earrings

Stand Studio

faux shearling jacket

Silk Pajama Top + Rinse Wash Denim

Denim for the win! Pair a dark-wash straight-leg jean with a striped silk Asceno pajama top, classic leather Chelsea boots for a bit of height and polish, then round out with Balenciaga’s Le City bag for model off-duty attitude.

Asceno

silk satin pajama shirt

Agolde

90s straight-leg jeans

Flattered

Barbara belt

Toteme

The City boots

Image may contain: Accessories, Bag, Handbag, and Purse

Balenciaga

small Le City peather satchel

Roxanne Assoulin

hoop earrings

Striped Night Dress + Knee-High Boots

For the stripe lover, make it twice as nice with Alex Mill x Schostal’s night shirt and another button-down knotted at your waist or worn over your shoulders. Complete with a slouchy bag, knee-high boots, and drop cord necklace.

Alex Mill

x Schostal nightshirt

Staud

Wally leather knee boots

Polo Ralph Lauren

striped shirt

Flattered

Alva big bag

Diane von Furstenberg

x L.G.R Raffaello sunglasses

Laoli

The Drop cord

Matching Silk Set + Studded Bag + Satin Slipper

Delos’s silk-satin sets are available in an array of colors and prints. Opt for this lavender and nude marbled print for a look that’s impactful yet not overwhelming, then complete with Khaite’s studded bag and Ancient Greek Sandals’s chocolate brown satin mules.

Delos

Gilbert jacket

Delos

Gilbert trousers

Lié Studio

The Elisa choker

Khaite

Elena bag

turtleneck top

Ancient Greek Sandals

The Slipper satin mules

Printed Robe Coat + Satin Pants + Kitten Heels

For a lady-of-leisure-inspired moment, opt for this Dries Van Noten robe inspired coat pair with navy trousers and a simple white tee. Accessorize with a single diamond necklace, Jimmy Choo animal print pumps, and Loewe Flamenco shoulder bag. A combination meant to make a statement.

Dries Van Noten

Raltonas coat

J.Crew

cosmo pants

Rare Carat

lab diamond necklace

Gap

Vintagesoft T-shirt

Jimmy Choo

Amelia 30 pumps

Loewe

Flamenco shoulder bag