JUST AS MANY Americans took their first fully vaccinated exhales, the Covid-19 Delta variant reared its head, plunging our collective psyche into a state of confusion and anxiety again. Workplaces are pushing back their reopening dates like flaky lunch companions who never meant you to take their invitations seriously in the first place. Perpetually in flux is the new normal. And the hybrid state of working from home and popping by the office, referred to by managers as “flex,” is, for many, the new full-time.

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Uncertainty aside, countless women are weary of toiling all day in sweatshirts and leggings. And whether they’re heading back to the office, sticking with remote Zoom meetings or balancing some mishmash of the two, a lot have a renewed desire to get dressed for work. But professional attire looks different than it did in February of 2019. Old norms have been shattered, which means that back-to-work shopping is less of a refresh than a reclamation, with women gravitating toward clothes that combine fashion cred with comfort and practicality.

“I’m seeing cashmere pantsuits that look like pajamas, waistband trousers and looser jackets,” said New York celebrity stylist Kate Young. She cites knitwear-heavy brands like Bottega Veneta, the Row and Victor Glemaud as leaders of the new-workwear movement. Chloe King, who works in luxury brand development in New York, believes that dressing for work now means embracing a freer silhouette and “taking up space in a new and different way.” She cites a JW Anderson dress that looks like an upside-down lightbulb and an oversize, drop-waist Christopher John Rogers dress as examples of the new uniform.

Liane Wiggins, head of womenswear buying at online retailer Matchesfashion, has seen her customers experimenting with this relaxed but still dressed-up aesthetic. She’s observed women mixing pieces that they once feared weren’t “work-appropriate,” like billowy boho tops (think Connie Britton’s Silicon Valley boss Zoomwear on “White Lotus”) with denim, statement handbags and blazers. Ms. Wiggins reports that in August, sales of blazers, which are experiencing a comeback, were up about 25% at Matchesfashion compared with the same period last year. But it’s not your typical stiff, navy blazers that are resonating. “We’re seeing a lot of prints and checks and herringbone,” she said. “Everyone’s reinventing her own wheel.” Here, how four working women across the country are rewriting the rules in their ideal looks.

NOT-SO-STRICTLY BUSINESS While working—and mothering—from home, Facebook executive Roberta Thomson (above) favors fun, colorful Zoom looks that she buys online. Dress, $395, jonathancohenstudio.com

“Colorful meets fun,” is how Silicon Valley executive Roberta Thomson described her personal style. While leaders in the tech world consider flip-flops and tees acceptable attire, Ms. Thomson generally prefers a dress and heels. “As a Black woman, I’ve always felt pressure to dress up and show up,” she said. “Even for doctor’s appointments, I put my best foot forward.” Facebook was among the first companies to send workers home at the pandemic’s outset and Ms. Thomson hasn’t visited her office there since March, 2020. Though the workplace will be open on a voluntary basis this fall, she has no plans to stop by her desk.

Consumed by daily back-to-back video meetings, Ms. Thomson focuses on what her colleagues can see. She shows up camera-ready with custom-printed nail stickers from ManiMe; brightly colored T-shirt turbans from Dallas brand You Go Natural and her signature red lip.

STAY-AT-HOME BOSS Roberta Thomson, seen here in a favorite look, plans to ‘dress up and show up’ even while working remotely.

Photo: Aubrie Pick for The Wall Street Journal, Hair and Makeup by Deb Dapolito

Diabetes runs in her family and she was inspired to lose weight while working from home. When curvier, she found she needed to try on clothes in-store to find a good fit. Now that she’s dropped 40 pounds, it’s easier to shop for clothes online or via Instagram. Her fall refresh includes a bold jaguar-print jumpsuit (with matching headband and face mask) by America & Beyond and Spanx’s denim jeggings.

Another Instagram discovery: press-on eyelashes by MoxieLash. She’s been alternating between a few “surprisingly easy” high-drama styles that pop on camera. Still, she’s unconvinced they’ll translate off-screen: “I may need to size down to something slightly less conspicuous when I start seeing people in broad daylight.”

GET THAT GREEN Now back at her desk, Citi Private Bank’s Ida Liu (above) has swapped strict black suits for jewel-tone dresses. Akris dress, $3,490, neimanmarcus.com

Before the pandemic, Ida Liu went to work in a smart black suit. “My closet was a sea of black,” she said. Over the past year, Ms. Liu, a member of the bank’s “critical staff” who have been coming to the office, has undergone a sartorial revolution. She’s swapped her suits for dresses, which she finds more comfortable, and has embraced jewel tones, which stand out in the Zoom meetings that sometimes keep her busy from 6 a.m. until midnight.

OFFICE PARTY Ida Liu’s bright new wardrobe reflects her excitement about seeing her co-workers in person at the office again.

Photo: Christian Cody for The Wall Street Journal

Early in the pandemic, Ms. Liu considered casual dressing. But she quickly learned it didn’t suit her. “I was a caregiver, virtual teacher for my kids, and working from home, and I missed having the routine of getting dressed for the office,” she said. “It’s a good separator for me. I would get dressed [for] Zoom and I would get changed at night.”

Starting this month, other employees at Ms. Liu’s New York office have been encouraged to come in to work a couple of days a week, comfort levels and health data permitting. She’s excited to see her co-workers in person, and her wardrobe, with its bright colors, skews upbeat, too. Two particularly festive additions: a form-fitting emerald wool Akris dress and a pink A-line Valentino number. Another recent purchase is a bell-sleeve Roland Mouret frock with a matching face mask and on-brand coloring. “It’s Citi blue,” she said.

CHECK ME OUT After getting fully vaccinated, Dr. Dina Elrashidy (above) celebrated by returning to her weekly blow-outs and dressed-up office attire, like this look. Jacket, $3,500, gucci.com; Dress and Gucci shoes, Dr. Elrashidy’s own.

Dina Elrashidy inherited her love of dressing from her father, whom she lost to Covid-19 in March, 2020. He was a dapper engineer who duly took his daughters to the mall near their Michigan home. She’s channeled that love of style into a dazzling shoe collection which, she said, her patients appreciate. “People really pay attention to a doctor’s shoes. One of my mentors taught me that during my rotation,” said Dr. Elrashidy, who favors Gucci, Chloé and Enrico Cuini.

THE DOCTOR’S BACK IN Dr. Dina Elrashidy finds wearing signature shift dresses, heels and white coat in the office instills a sense of normalcy for her and her patients. Dress, $3,150, Chanel, 212.355-5050; Chanel shoes, Dr. Elrashidy’s own

Photo: Akilah Townsend for The Wall Street Journal, Hair and Makeup by Denise Ferguson

During the 11 years she’s practiced dermatology, she’s developed a uniform of statement heels, tailored shift dresses from brands like Akris, Black Halo and Veronica Beard, and a slim-fit Medelita doctor’s coat. “There is something about being a female doctor where a white coat gives you more respect,” she said.

When her clinic reopened last summer, she shifted to scrubs and sneakers. But dressing down made her uneasy. “[The sneakers] were Yeezys, but still, I was like, ‘No, I can’t do this anymore,’” she said.

Once fully vaccinated, she celebrated by returning to her weekly blowouts, body-conscious dresses and parade of striking-yet-comfortable heels. “They make me happy, and it really made people feel more normal to see me back in them,” she said. For fall, she’s bought shift dresses from office-wear line Of Mercer, and has her eye on Fendi’s rhinestone, kitten-heel mules. “I really missed getting dressed up,” said Dr. Elrashidy. “It makes me feel like there is more normalcy.”

TINSEL TOWN Helen Toomer (above) in her cloud-print Crocs, new Rachel Burke rainbow jacket, and the extra-wide Pleats Please Issey Miyake pants she found at Hudson, N.Y. boutique Kasuri.

“I like clothes that bring me joy,” said Helen Toomer, an art-world dynamo who, early in the pandemic, relocated from Brooklyn to New York’s Hudson Valley full time with her husband and young son. The co-founder of Stoneleaf Retreat artists’ residency and Art Mamas Alliance and founder of the Upstate Art Weekend festival, Ms. Toomer has long sought out eccentric outfits—particularly those that include sequins and tinsel. While Ms. Toomer has worked from home for years, the pandemic briefly dampened her appetite for flamboyant fashion, and she spent much of the last 18 months in country-friendly roll-neck wool dresses and fuzzy slippers. But when that cozy fare got old, she buoyed her mood by hanging her outré garments like works of art and prancing around the house in wild outfits.

PRIMARY ATTRACTION Arts organizer Helen Toomer—seen here in a typical look, alongside Christopher Thomas Campbell’s painting, ‘Blaze Painting,’ and sculpture, ‘Chossy Flotsam’—has retired schlump wear and resumed dressing joyfully.

Photo: Georgia Hilmer for The Wall Street Journal

Ms. Toomer and her outfits will prance elsewhere come fall, when artist studio visits and art fairs will pack her schedule. For New York fair the Armory Show in September, she’ll wear a limited-edition mustache-print mask by artist Catherine Opie; cloud-print Crocs; and a new rainbow tinsel jacket by Australian designer Rachel Burke. During a recent visit to Hudson, N.Y. boutique Kasuri—a wellspring of avant-garde attire—Ms. Toomer also purchased a pair of black Pleats Please Issey Miyake pants. Equally suitable for events and doing paperwork at home, the pants appealed because of their extreme width. “I like clothes that create big shapes and silhouettes,” Ms. Toomer said. Her key fall item, however, is something smaller: a face mask from sustainable fashion brand Collina Strada. “It has these big ribbons that fall down the sides of my face,” she said. “If you’ve got to wear a mask, make it fashion.”

Clothes to Get the Job Done

An assortment of stylish pieces well suited to working from home, the office or both

Clockwise from top left: Dress, $830, janeatelier.com; Blazer, $650, veronicabeard.com; Leggings, $141, refine-store.com; Baum Und Pferdgarten Blouse, $159, nordstrom.com; Pumps, $875, rogervivier.com

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