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5 Days, 5 Ways: Vintage Sleep Shorts You Can Do *Checks Notes* Everything In

A pair of vintage blue plaid Bill Blass sleep shorts from Etsy has become a staple in my outfit rotation since entering quarantine, steadily rising in the ranks of the small faction of my closet I still wear routinely. I am now fully convinced that the ease of wearing cozy, stretchy pajama shorts is undeniable when occupying the space in limbo between my apartment and the great outdoors.

I’m not immune to craving some variety, though, which is why I’ve been challenging myself to style them in different ways that broaden my understanding of contemporary comfort in the quarantine era. It may or may not be an excuse to simply keep some portion of my pajamas on all day (because yes, I actually sleep in the sleep shorts), but I’ll let you be the judge. Below are five different styling approaches to this unconventional wardrobe hero.


5 Days, 5 Ways: Sleep ShortsFor a day of WFH, I typically don’t give a fruit whatever ensemble manifests; prioritizing comfort has been an invigorating daily self-care practice. My approach when greeted with my options involves a pair of sleep shorts, a semi-legit long sleeve top and exactly one piece of jewelry for added flair. Rolling my sleep shorts twice at both the waist and hem felt cheeky, so it stuck. The look was completed with a beachy Gimaguas necklace and two hair accessories, the jaw clip serving as an emergency backup.

Pup Walk

5 Days, 5 Ways: Sleep ShortsWalks through Brooklyn Heights Philo have become a great excuse to briefly sport a favorite item or accessory when seeking the thrill of human validation. For this particular outing, I paired my sleep shorts (rolled once) with a favorite vintage terry top and fancy socks-plus-sneaks combo. This is a formula I’d wear a million times over. With a functional hat and my pup in tow, I was out the door.

Date Night

5 Days, 5 Ways: Sleep ShortsHello, Friday night, let’s up the ante for a living room date night with my partner. I’ve never had the right opportunity to wear these vintage Moschino mules outdoors, so I’ve enjoyed reaching for them at home when the desire to put on nice shoes overtakes my physical being. Staying inside for the evening ironically lends itself to wearing impractical shoes. I remained in my semi-legit WFH top but added an artfully placed colorful vintage scarf for failsafe summertime accessory elevation. It’s allegedly now the weekend, so I transitioned the look to evening wear with a pearl-necklace-as-anklet and sneaky crimson lip to demarcate the end of the work week.

To the Grocery, and Beyond

5 Days, 5 Ways: Sleep ShortsThese days, my local Trader Joe’s is my primary opportunity to see and be seen by other people, so when I’m there, I try to pull out the quote unquote outfit goods, but it’s also a risky environment in regards to close contact, so I stop short of anything I can’t launder soon after. My trusty sleep shorts were up to the task, along with a vintage T-shirt and, critically, a mask. You can count on me to roll up with my own reusable tote for bagging groceries; in this case, it’s a formerly identified airplane carry-on. My favorite part of this look are the recycled rubber boots, my only purchase of quarantine. Wearing boots out-of-step with the sunny forecast creates a friction that feels just right.

Outdoor Adventure

5 Days, 5 Ways: Sleep ShortsSeeking any excuse to test-drive my partner’s recent button-down buy, I snuck it on and layered it with a scarf-as-top. Behold the saucy inward waistband tuck of the sleep shorts–perfectly suited to a socially-distant outdoor adventure strolling in my local park. I love sunglasses and treasure my small collection; this vibrant oversized pair makes me feel instantly empowered.

Styling sleep shorts for a range of indoor and outdoor pursuits presented a new challenge to dressing that felt invigorating to tackle. By the end of the week, my dressing perspective felt thoroughly refreshed; I was pleased to uncover a summer wardrobe hero item moonlighting as a pair of sleep shorts that made me feel comfortable and confident with each wear. I’ll be sticking with Sleepleisure for the foreseeable future and look forward to adding sleep capris and camisoles to the rotation.

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