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These 5 Pajama Outfits Are Perfect For The Busy Fashion Girl On The Go

It’s sleepwear as streetwear.

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Monique Olivia Black how to wear pajamas out
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Hi, I’m Emma, and I’m a maximalist with a soft spot for ‘ugly’ clothing. I self-identify as a Weird Girl, someone who gravitates toward the whacky and unconventional. But above all else, and what I’ve discovered to be the most paramount aspect of my style philosophy, is that I’m a lazy dresser. I prioritize comfort and convenience first and foremost. Thus, when I began brainstorming my sartorial game plan for summer 2022, I had an epiphany: Given my affinity for high-comfort, low-energy styling, it’s time I investigate how to wear pajamas out of the house. Because, really, what clothing could be more streamlined and effortless than those I wear to bed?

I started from scratch on this quest of mine to master sleepwear as streetwear (I quite literally Googled ‘pajamas outfits that don’t look like I overslept and left the house in a hurry?’), and my initial research presented me with a slew of slip dress outfit ideas. And while I absolutely endorse the supermodel-vetted ‘90s-era look, I knew my individuality complex would only feel satisfied by more maximal and unique ensembles. Furthermore, given that silk is susceptible to sweat stains (a lesson I learned the hard way after borrowing my roommate’s Rag & Bone slip dress on a particularly humid June evening), it’s not a material I see myself reaching for during a summer that’s experiencing unprecedented heat waves.

So I narrowed my search to eccentric pajama outfits in breathable materials — linen, cotton, and gauze, for example — and turned to the fashion mavericks of Instagram for assistance. And after some thorough scrolling, I found five pajama outfits that tick both boxes in that they offer comfort while delivering a sui generis (that, ahem, is Latin for “unique”) impact that makes my maximalist heart sing.

Ahead, you’ll find those bold ensembles as well as a me-approved edit of pajama staples to shop that’ll help you replicate the looks, too.

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Boxer Shorts With A Cutout Top

I myself already own a pair of boxer shorts. They’re blue gingham and made of breezy cotton blend, a particularly triumphant find from an Adam Selman sample sale I attended in 2019. However, I’ve relegated them to my casual, errand-running rotation, wearing them solely with roomy tee shirts and sneakers, and have yet to try wearing them in more ambitious outfits. However, stylist Elizabeth Cardinal Tamkin’s technique of pairing Comme Si’s La Boxer Classica with a sultry keyhole blouse caught my eye and is one combo I’ll be trying this summer.

Shop a selection of boxer shorts, below, and then take a leaf out of Tamkin’s book by teaming yours with a sensual cutout top.

A White Cotton Nightie & Sneaks

If an outfit boasts an unexpected clash of aesthetics — a cottagecore take on grunge, an amalgamation of preppy-meets-utilitarian styles, or a girly yet sporty combo — I’m sold. As such, model Imani Randolph’s white nightgown teamed with low-top Nike sneakers is right up my alley. The breezy nightie taps into the soft naiveté of childhood sleepovers, while the athletic footwear provides a slight streetwear edge.

A PJ Short Set With Clogs

I, like thousands of others, have become enamored with the easy, one-and-done magic of a matching set during the loungewear craze of recent years. Thus, I figured the next logical step would be to integrate a pajama set into my collection of co-ords (RIXO’s lime green gingham two-piece separates are sitting in my Net-a-Porter cart at this very moment). So, this summer, you’ll see me scurrying around downtown Manhattan wearing a printed poplin PJ set and my favorite pair of embellished clogs à la influencer and fashion consultant Alyssa Coscarelli.

Bloomers, A Vest, & Loafers

Allow It girl Reese Blutstein to convince you why bloomers — yes, as in the 19th-century undergarments — should be in your summer rotation. A more out-there alternative to bike shorts, the retro bottoms have become a surprising favorite amongst the style set. Plus, they come in a range of silhouettes: Some pairs boost tiers of smocking or ruffles — like Blutstein’s from Kyiv-based brand BIBLIOTHEQUE nationale — while others stick to the traditional balloon-like, tapered design.

And for all the fashion history buffs out there, the bottoms have a storied past you’re sure to find fascinating. The shorts are named after Amelia Bloomer, an early American suffragist, writer, and editor who wore the drawers so that they peeked out beneath her skirts. Bloomer wore the style so often and famously that the pantaloons became a prevalent symbol of female empowerment during the era. Interestingly enough, given 2022’s wave of neo-neofeminism and regression of women’s rights, I can’t help but think today’s bloomer trend is just another example of the cyclical nature of fashion at work. But, alas, that’s a think piece for another day.

An Open Pajama Top

Instead of stashing a light, just-in-case cardigan in my summer carry-all, I’ll be keeping a pajama top in my purse. It provides the perfect amount of light yet cozy coverage you want on a cool summer evening or when encountering especially chilly blasts of AC while out and about. And, as stylist and fashion writer Michelle Li demonstrates, a PJ shirt worn open and unbuttoned gives off a laissez-faire air that I, as an insouciant dresser, simply cannot resist.

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