Drawstring pajama pants are the ultimate canvas for versatile styling. With the right pairings, you can go from sleepy to street-chic without sacrificing comfort. The key lies in contrast—mixing soft, relaxed bottoms with sharper or styled pieces. Don’t be afraid to accessorize, play with silhouettes, and treat your pajama pants like any other stylish trousers. Comfort is here to stay, and pajama pants are leading the way.

7 Ways to Style the Drawstring Pajama Pant—Summer’s Most Relaxed Essential

By Cortne Bonilla

From https://www.vogue.com/

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Carefree and effortless are just two adjectives we’d use to characterize the disposition of dressing in the summer. And the season’s go-to style staples include should be pieces that reflect that nonchalant ease—essentials that can be worn day and night; for work and play. We’re talking button-up shirts, raffia handbags, flip-flops, and of course, pajama-like drawstring pants.

Meant for anything but sleeping, chic pajama-style pants from Toteme and The Row to Aligne and Donni are must-have additions that will become a dependable piece in your summer rotations. While inherently laidback, these bottoms can appear perfectly polished when styled appropriately. To prove our point, we’re mapping out seven pull-on and drawstring outfits that you can (and should) comfortably wear on repeat this season.

From the city streets to the seashore, poolside options from Loewe and even Zara can double as chic cover-ups, wearing well with everything from little brown bikinis to woven hats and carryall bags. We can’t forget about those joyous, never-ending summer nights, either. Luckily, there are striped and silky pairs that can be dressed up with halter tops, cropped blouses, and plunging necklines alike. Below, shop seven pajama pant outfits that are equal parts casual and cool.

Red, White, and Snakeskin

Sometimes, a less-is-more approach is all you need for a curated look. Take this ensemble, for example. Color match a red tank top with Staud’s Port tote, and let the The Row’s subtly-striped trousers offset Amina Muaddi’s snakeskin heeled thong sandals. Minimalist yet impactful!

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Aritzia

Homestretch rib squareneck waist tank

$25

ARITZIA

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The Row

Hypnosta striped straight-leg drawstring pants

$1,050

BERGDORF GOODMAN

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Staud

Port tote

$295

STAUD

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Amina Muaddi

Juliette snake-effect leather sandals

$830

NET-A-PORTER

Walking on Sunshine

Looking to splash some color into your summer capsule wardrobe, but in a subtle way? Turn to Toteme’s mellow yellow pajama-like pants for repeated sartorial success. Style yours with the matching button-up shirt, Lié Studios’s newest raffia tote bag, and Emme Parsons strappy flat sandals. You truly can’t go wrong.

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Toteme

raw raglan shirt

$540

TOTEME

Toteme

Twisted Seam Boxer organic cotton pants

$450

NORDSTROM

$450

NEIMAN MARCUS

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Lié Studio

The Bianca woven raffia tote

$500

NORDSTROM

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Emme Parsons

Loop satin sandals

$525

NET-A-PORTER

Meet at the Rooftop Pool

When your kaftans and sarongs just won’t cut it, opt for Zara’s silky, printed drawstring pants instead. They’re the perfect cover-up for a chic one-piece swimsuit. Complete the look with Dragon Diffusion’s woven tote—ideal for stashing your sunscreen, flip-flops, and a poolside read. Then, protect yourself against harmful UV rays with Zimmermann’s fringed sun hat.

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Mango

strappy rib swimsuit

$90

NORDSTROM

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Zara

printed pants

$70

ZARA

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Zimmermann

fringed macramé raffia bucket hat

$395

NET-A-PORTER

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Dragon Diffusion

bamboo Triple Jump tote

$430

SHOPBOP

All Aboard!

Channel summer’s nautical spirit with the requisite stapes: a pair of wide-leg linen pull-on pants and a preppy polo shirt in a classic seafaring color combo—white and navy. Raffia espadrilles and L.L Bean’s Boat & Tote anchor the look (sorry, could knot resist.)

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Cos

merino wool-blend polo cardigan

$130

COS

Aligne

Alara linen wide leg trouser

$145

ALIGNE

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Boat and Tote

$35

L.L BEAN

Alaïa

paper straw ballerina flats

$1,450

SSENSE

Hook, Line, and Sequin

We’re no longer keeping our sequins, shells, and other playful embellishments hidden until vacation. Make every day a special occasion with J.Crew’s sequined tank top—the perfect juxtaposition to a pair of striped Alex Mill drawstring pajama pants. Keep it daytime appropriate with Khaite’s Zoe tote and The Row’s fisherman sandals.

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J.Crew

crochet shell-embroidered tank top

$98

J.CREW

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Alex Mill

Riley pant

$175

ALEX MILL

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Khaite

Zoe tote

$1,580

KHAITE

The Row

off-white fisherman sandals

$1,090

SSENSE

$1,090

NET-A-PORTER

Life is Like a Box of Chocolates

Unlike the typical pajama pant, these from Donni are designed in a chocolate brown hue for a more sophisticated feel. Wear yours with a summer-ready blazer and accessorize with Banana Republic’s raffia bucket bag for a fashion-forward touch.

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Gia Studios

Dori jacket

$896

NORDSTROM

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Donni.

linen simple pants

$175

DONNI

$175

DONNI.

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Banana Republic

x Sensi Studio straw bucket bag

$190

BANANA REPUBLIC

Aeyde

Melody leather flip flops

$295

NET-A-PORTER

Bohemian Rhapsody

Nothing says summertime quite like a little halterneck top, especially this one from Liberowe with its all-over floral print and peplum silhouette. Just add in Khaite’s luxe drawstring pants and Savette’s suede Tondo bag to play up the boho-inspired tones.