7 Pajama Pant Outfits That Are As Casual As They Are Cool

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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.

Vogue’s Summer Pajama Pant Picks:

• The Subtle Staple: Uniqlo linen-blend easy striped pants, $30
• The Butter Yellow Pick: Toteme Twisted Seam Boxer organic cotton pants, $450
• The Linen Find: Aligne Alara linen wide-leg trouser, $145
• The Classic Stripe: Alex Mill Riley pant, $175
• The Luxe Pair: Khaite Trenton pant, $1,380
• The Casual Chocolate Option: Donni. The Linen simple pants, $175
• The Tried-and-True: J.Crew Soleil linen pants, $98
• The Investment Pick: The Row Hypnosta striped straight-leg drawstring pants, $1,050
• The Poolside Favorite: Zara printed pants, $70

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!

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.

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.

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.)

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.

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.

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.

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