Carefree and effortless are just two adjectives we’d use to characterize our ideal of summer dressing. And the season’s go-to style staples should include pieces that reflect that nonchalant ease—essentials that can be worn day or night; for work or 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 are popping up all over the market, as must-have additions that will become a dependable piece in your late spring and summer rotation. 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 city streets to the seashore, poolside-appropriate options can double as chic cover-ups, wearing well with everything from your trendiest swimsuit to your favorite sandals. And we can’t forget about those joyous, never-ending summer nights, either. Luckily, there are chic, silky pairs that can be dressed up with tailored tops, cropped jackets, and easy tees alike. Below, shop seven pajama pant outfits that are equal parts casual and cool.

Color Story

Balance Khaite’s absinthe green satin pants with unexpected neutrals—a heather gray tee and pop of burgundy (in the form of a chic wedge sandal) will do the trick.

Down to Earth (Tones)

Keep it casual in Zara’s cotton pull-on pants, grounded with an equally easy lightweight jacket in khaki. Mesh flats and your favorite sunnies give the look a fashion-forward push.

Dinner Plans

If you can’t wear pajamas for a night on the town, you can wear the next best thing… lustrous, elastic-waist trousers and a tailored top. Chic heels and a going-out bag prove that polished and comfy can co-exist.

Aperitif Hour

Golden hour rooftop evenings are on the horizon and a sweet, summery look is in order. Slip into satin pants in this season’s trending butter yellow shade, with a cute top, simple sandals, and beaded bag.

Quick Dip

A post-swim ensemble is as easy as one, two, three—all you need is a matching pajama-inspired set like this cheerful striped pairing by Sanderlak, and your most reliable summer flip-flops.

Longer Layers

The pull-on pant lends itself well to our current dress-over-pants styling obsession. Cherry red silk trousers are the perfect match for a lingerie-inspired top layer. Modern, sculptural accessories ground the ensemble.

The Blues

We love a bit of pattern play, and it’s easy to do when you keep the color palette monochromatic. Donni’s cult-favorite Pop pant in classic a navy stripe is a lovely companion to Dôen’s paisley scarf top.

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