Workleisure Outfits Are Defining Our Style in Uncertain Times

Be prepared for whatever this fall has in store.

woman in workleisure outfit


Dressing for the job you want in 2021 is turning out to be as complicated as it was in 2020. A year ago, a return to the office felt like a fantasy. We had the Zoom top, a looming election, and no vaccine in sight. Brands largely focused on cheerful athleisure in an attempt to lift our spirits amidst prolonged isolation.

Thanks to the widespread rollout of vaccines, early 2021 took on a new tone of apprehensive hope, until this summer burst forth as the start of a promised "return to normal." Luxury brand sales gained traction as we all began to plan looks for our reemergence into the world, often much bolder than our pre-pandemic style. According to Lyst's quarterly report based on consumer data, social media mentions, and conversion rates, spring 2020's hottest brand was Nike, while spring 2021's was Gucci.

Now, things have proven to be a bit unpredictable again, and recent uncertainty lands shoppers somewhere between athletic performance wear and fantastical velvet. Instead of dressing for the job you want, Vanessa Friedman advised "dressing for the mindset you want" in her 2020 New York Times piece "Behold, ‘Workleisure," and this tip seems to hold true a year later, if a bit more dynamic than when the world was on lockdown.

Google's three-word plan for returning to work, "Flexibility and Choice," best encapsulates the energy informing shoppers’ purchasing power amid this confusing moment. There’s no reason blurred lines and ever-changing conditions should make getting dressed for the day a point of stress; Instead, some smart planning can help us to approach the moment right. Workleisure meets us where we are: unsure, apprehensive, and ready to retire the tie-dye sweatsuit. Comfortable yet presentable, today's smartest pieces are striking a balance we perhaps always needed, and are sure to get lots of wear, whether you're returning to in-person settings or staying home a bit longer than expected. Ahead, learn more about the key components defining workleisure outfits, as well as the best pieces to shop now so you can stay ready for whatever the coming months have in store.

What Is Workleisure?

Workplace dressing has been evolving in a more casual direction for decades. The '50s secretary sets and '80s power shoulders were already gone—the pandemic simply kicked the casual progression into high gear. After the charm of a workday spent entirely in pajamas wore off, consumers began imagining wardrobes that could carry them from a Zoom board meeting in the kitchen to an eventual return to the office cooler. Workleisure outfits adapt the comfort we’ve adjusted to for the world we hope to reenter.

So what, exactly, does the future of workwear look like in a hybrid world? “The main buying factor during the pandemic has largely been comfort and we don't see that going away; Rather, newer style hybrids will emerge, like elastic-waist pants or drawstring trousers,” explains Melissa Moylan, vice president and creative director at the consumer insight and trend forecasting company Fashion Snoops. “Casualization will be key.”

Matt Feniger, director at Tobe TDG By The Doneger Group, echoes Moylan’s sentiment. “A continuous design direction is putting 'the broccoli in the brownie' if you will,” he explains. “That means working comfortable construction into more polished pieces, whether that means front or back elastic waistbands, fabrics with two-way stretch, or double-knit fabrics for styles with both structure and comfort.”

House Shoes Take the Streets

Perhaps no category has changed as much with pandemic dressing as footwear. Over time spent largely at home, heels and pinchy loafers gradually lost much of their appeal, with the bliss of an orthopedic sole replacing more formal shoes in a trend that seems likely to last even in a hybrid state. Birkenstock, a heritage brand with an evergreen appeal, stepped into the spotlight. These days, I've been unable to leave my Brooklyn apartment without seeing a dozen pairs of the iconic silhouette. People who discovered the comfort of Birkenstocks' unassuming footbed—unchanged since the 1930s—are now eager to take the shoes into their “before lives.”

Equally synonymous with pandemic dressing are Ugg sheepskin slides. “We acquired a lot of new customers in 2020 through our Fluff Yeah style and work from home," says Andrea O'Donnell, the brand's president. "Now it’s our job to keep them engaged and loyal to Ugg.”

It wasn’t only the Fluff Yeah style that stood as a symbol of the early pandemic. “Models and It-Girls like Kaia Gerber and Kendall Jenner were seen numerous times out and about in the Classic Ultra Mini—really solidifying the new silhouette as the 'unofficial' model-off-duty shoe,” O’Donnell explains.

Shop The Look

And then there’s the underdog class of small brands finding their voice in a sea of change. One such label that ended up all over my Instagram feed is Sabah, which specializes in leather slipper-style shoes handmade in Turkey. It checked out: The shoes' versatility and simple silhouette—and in some cases, shearling-lined comfort—seemed to perfectly fit into a workleisure outfit. “We've seen a growing interest in our Babas, but without shearling lining, which are super versatile—great house slippers and also perfect for slipping out for a stroll, to the beach, etc.," says Mickey Ashmore, Sabah's owner and CEO. "They're playful and hopeful, while still being practical and definitely a bit more social.”

Flexibility in Wearability

Hill House Home's Nap Dress is another portrait of a smaller brand finding itself in the right place at the right time. Through providing an elevated-yet-comfortable option for wearing both around the house and to summery gatherings, the label has exploded in popularity, with its dresses becoming repeated sellouts. Adapting into a more hybrid lifestyle, you can now find more outdoor-facing options in the line, like The Desk Sweater, meant for use in chilly, air-conditioned offices.

Other brands, like Lululemon, saw massive spikes in sales earlier in the pandemic and now are among the trend of activewear brands reimagining clothing for a return to work, whatever that looks like. According to Lululemon, their City Sleek 5 Pocket 7/8 Pants were “designed to be on the move on work days, after work, or weekends.” The sweat-wicking, wrinkle-resistant fabric hardly gives away the pants' status as a hybrid option for work and play, catering to the versatility shoppers are demanding.

For other brands, the embracing of a fluid sense of normal has always been instinctual. AYR’s ethos has always been one of wearability. “Pre-pandemic, AYR's bestsellers were jeans. Over the past year, they've been eclipsed by a shirt called The Deep End," explains Maggie Winter, the brand's co-founder and CEO. "It's an oversized button-down that perfectly combines comfort and professional look and feel pulled-together without much effort. Even Oprah has worn it on Zoom calls."

With recent lifestyle changes, AYR's flexible philosophy has come to adapt well to society's changing preferences in clothing. “It's casual Fridays all day, every day, All Year Round," Winter says of why workleisure outfits are so popular right now. "The delineation between spaces has blurred. We're always at work, we're always at home, we're always parenting, we're always cleaning. We need apparel that can do it all—more than ever.”

On-the-Go Bags

In our conversation, Feniger alluded to a new developing category along with the workleisure outfits' loosening of dress codes. “Silhouettes are also getting more roomy and relaxed, especially in bottoms, and we’ll see more novelty focused around the accessories and shoes categories,” he explains.

For a brand like Dagne Dover, whose tagline is “making bags for humans getting the most out of life,” gray area isn’t all bad. The label's Ace Fanny Pack experienced a huge resurgence during the pandemic for its hands-free access and compact size. The Dagne Dover team took the cultural slowdown to re-source many of their existing materials to incorporate more eco-friendly options. “We’ve created every bag with the assumption that people might want to ride their bike to the office, or go on a walk during their lunch break," says Jessy Dover, the brand's Chief Creative Officer. "Our materials and designs cater to a life in motion.”

Workleisure outfits are for a life in motion, for a world in flux. They eschew tradition in an attempt to embrace the landscape we wake up to every morning. Whether through an elastic waistband, a neoprene tote, or shearling-lined gardening shoes, this trend feels just like dressing in a security blanket to help you conquer whatever kind of schedule you're navigating these days—a win for joyful style in our book.

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