Upgrade Your Look When You Work From Home

What to Wear to Work—When You Work at Home

Working remotely—long the territory of slobby creatives—has become newly social thanks to co-working spaces and teleconferencing. Here’s how to upgrade your look without sacrificing comfort

What to Wear to Work—When You Work at Home

Working remotely—long the territory of slobby creatives—has become newly social thanks to co-working spaces and teleconferencing. Here’s how to upgrade your look without sacrificing comfort

ILLUSTRATION: VICTORIA TENTLER KRYLOV

I WAS STANDING in my closet, struggling to choose an outfit that would allow me to magically transition from freelance writing at home to a work lunch and still be suitable for my afternoon shift as unpaid chauffeur for my kids. The effort almost made me nostalgic for my years spent chained to a desk as a magazine editor. Sure, my colleagues could be brutally condescending, the pay wasn’t great and the pressure to dress on-trend was relentless, but at least I knew what to expect: aching feet from stomping around Manhattan in heels, mountains of shopping debt and clear-cut boundaries between work and play, with wardrobes for both.

It’s been 17 years since I’ve regularly reported to an office, and since then many of the rules about how we work, and how we dress for it, have changed. Last year, a report from research group Global Workplace Analytics and FlexJobs noted that the number of people who describe themselves as “telecommuters” has increased 115% since 2005, which translates into roughly 3.7 million of us who work outside of a traditional office more than half the time. Here in Los Angeles, my work appointments bleed into my personal time as I drive around town, so I need outfits that function for both. To stay focused and on task for the professional parts, I often err on the dressy side.

THE NEW WFH WARDROBE / FOR NETWORKING AT A COFFEE SHOP

PHOTO: F. MARTIN RAMIN/THE WALL STREET JOURNAL, STYLING BY ANNE CARDENAS

Pair a cozy sweater with on-trend pants, and that agent at the next table might actually ask about your screenplay. Sweater, $125, cosstores.com; Pants, $325, apc-us.com; Loafers, $645, tods.com; Bag, $3,100, Prada, 212-334-8888

This philosophy also applies, at times, to toiling at home. When I have a Skype interview, I reach for a pair of gold statement earrings, a Kosas lipstick and a fashion-y blouse from Isabel Marant or Dries Van Noten. No one needs to know that I’m barefoot in my ripped Levi’s from the waist down. If a deadline’s looming and I need the buzz of human activity to jump-start my brain, I’ll throw on my wide-legged, one-step-above-jeans Jesse Kamm pants and a quilted jacket and join the hordes of other professional nomads looking for Wi-Fi and an empty chair in a cafe. There’s no strict uniform for this disjointed calendar of commitments and environments. Working from home these days, where we are often required to network both in person and online via smartphone, requires a flexible strategy. Vanished are the days when working from home meant being invisible.

The founders and designers of Sydney, Australia-based Bassike, Deborah Sams and Mary Lou Ryan, addressed these challenges when they created their line of tailored-yet-casual pieces in 2006. “We were thinking about everybody’s lives, how we’re all juggling, and wanted to create wearable, practical clothes that are easy to launder and care for,” said Ms. Sams. She and Ms. Ryan are eager to provide solutions for our new, collective work-from-everywhere lifestyle. For example: A shirt dress that you can wear over leggings.

THE NEW WFH WARDROBE / FOR A STRESSFUL SKYPE SESSION

PHOTO: F. MARTIN RAMIN/THE WALL STREET JOURNAL, STYLING BY ANNE CARDENAS

Focus on the waist up with this strikingly collared shirt and elegant earring combo. Shirt, $138, shopdoen.com; Earrings, $4,160, tenthousandthingsnyc.com

While a flexible schedule can be liberating, some freelancers set self-imposed rules. “I went to a prep school with a dress code,” said Andrea Arria-Devoe, 43, a contributor to lifestyle website Goop, a documentary film producer and an advisory board member for the Plastic Pollution coalition. “So it’s been ingrained in me that dressing nicely makes you sit up a little straighter in your chair.” Her new uniform involves dressed-up separates—polished jackets and pants—that are elevated enough for her packed schedule of meetings. She depends on pieces from independent New York designers like Caron Callahan, often wearing the same outfit a couple of days in a row (more environmentally sustainable and definitely a freelancer-only luxury).

‘Vanished are the days when working from home meant being invisible.’

Katharine Zaleski, who works at home as president and co-founder of Manhattan-based PowerToFly, an organization that provides companies with the services to meet diversity hiring goals, said that the primary criterion her clothing has to meet is whether it works for her morning school drop-offs via scooter. After that, she might add a nice jacket for a virtual conference, but her professional wardrobe is now completely on her own terms: “Back when I worked in an office full time,” said Ms. Zaleski, 37, “I got stomach aches when I had to wear a restrictive suit or dress all day long.”

Leaving behind the sense of sartorial dread that accompanies zipping up “professional” suits and dresses is one of the perks of a flexible job. When Nilou Ghodsi, the founder and owner of the Los Angeles store and online boutique Heist, transitioned from a career in finance in 2002, she also left behind a closet full of Theory suits. Now Ms. Ghodsi, 49, wears the same types of pieces she sells at her store to a clientele heavy on women who work erratic schedules in creative fields: colorful scarves, cashmere sweaters, flattering pants and interesting jackets.

THE NEW WFH WARDROBE / FOR A LAST-MINUTE CLIENT MEETING

PHOTO: F. MARTIN RAMIN/THE WALL STREET JOURNAL, STYLING BY ANNE CARDENAS

Buckle down at home in this smooth bodysuit, then throw on a fab coat on your way out. Coat, $2,990, Carolina Herrera, 212-249-6559; Shirt, $225, frame-store.com; Bodysuit, $188, livetheprocess.com; Rosetta Getty Slingbacks, $690, net-a-porter.com

When days are unpredictable, creating structure can be the secret to success. Podcast producer Jenelle Pifer, 31, starts her at-home work days by “commuting” around the block, taking a 20-minute walk around her Brooklyn neighborhood to signal the start to her day. Although she appreciates the freedom to wear sweatpants if she feels like it, Ms. Pifer generally dresses much as she did when she worked at an office. “Working from home makes you appreciate that there’s no better person to dress for than yourself,” she said.

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