On-the-Job Style

Four women—with four very different careers—share their secrets for looking the part (while still looking like themselves).

The Buyer

Alexandra Willinger, associate buyer at Intermix, is essentially paid to be on-trend. It’s her job to know what the high-end boutique’s customers want before they do, which means test-driving the latest—often edgiest—pieces. “I’m always taking risks,” she says.

“A moto vest pulls an outfit together just like a blazer—but it’s so much cooler.”

Leather vest, $1,295, IRO. Madison, 855-745-9900 for locations. Top, $425, Theory, Theory.com for locations. Pants, $395, See by Chloé, Saks.com. Sandals, $595, Rag and Bone, Intermixonline.com. Tote, $565, Diane von Furstenberg, Dvf.com

©Lucky

1 of 17 Courtesy of Rebecca Greenfield

“A wild outfit needs a classic bag. I’m a Virgo—I can’t take too much chaos.”

Dress, $790, Thakoon, Shopbop.com. Bracelet, $145, Jennifer Zeuner Jewelry, Intermixonline.com. Bangles, $98 each, Gerard Yosca, Intermixonline.com. Mala bead bracelets, $48 to $138 each, Lisa Freede Jewelry, Lisafreede.com. Ring, $275, Alexisbittar.com. Belt, $52, Lauren Ralph Lauren, Zappos.com. Bag, $450, See by Chloé. Select Nordstrom, 800-933-3365

2 of 17 Courtesy of Rebecca Greenfield

The Buyer

“Ideally, I’d dress like it’s Coachella all summer. A stretchy printed dress is the next best thing.”

Ikat dress, $390, Thakoon.com. "Endless summer" necklace, $480, Lulufrost.com. "Lighthouse" ring, $155, Lulufrost.com. Leather "Brookton" heels, $295, Kors Michael Kors, 866-709-5677 for locations. "Mini Harper" bag, $395, Diane von Furstenberg, 212-542-5754

3 of 17 Courtesy of Rebecca Greenfield

The Buyer

“I hope the wedge-sneaker trend never ends! I’ve gotten used to wearing high-tops to work.”

"Victor" blazer, $398, Diane von Furstenberg, Dvf.com. Tank, $76, Clu. Sweet William, Hinsdale, IL, 630-920-8444. Jeans, $196, Mother, Barneys.com. Necklaces, $120 to $310 each, Jennifer Zeuner Jewelry, Intermixonline.com. Sneakers, $395, See by Chloé. Solestruck, Portland, OR, 503-224-3591. Bag, $1,500, Mulberry, Intermixonline.com

4 of 17 Courtesy of Rebecca Greenfield

The Entrepreneur

Melissa Thompson, cofounder of TalkSession, a tech start-up, is all business. Meeting with venture capitalists and programmers requires chic, minimalist outfits that look totally profesh (but make her feel pretty).

“The fastest way to get amped up for a big industry event: Put on a red dress. You can’t help but feel optimistic, and you’ll definitely get noticed.”

Cotton "play the wild card Selita" dress, $578, Kate Spade New York, Katespade.com. "Lawford" eyeglasses (shown throughout), $350, Barton Perreira. Silver lining opticians, NYC, 212-274-9191. Suede "Allyy" pumps, $86, Steve Madden, Amazon.com. "Wicker Park little Sherri" bag, $278, Kate Spade New York, Katespade.com

5 of 17 Courtesy of Rebecca Greenfield

The Entrepreneur

“A tailored dress is my canvas. Then I just swap out my shoes and bag—and add smoky eyeliner!—to take it from day to night.”

Lace Dress, $128, A/X Armani Exchange, Armaniexchange.com. Pumps, $85, Mango.com. Bag, $80, Melie Bianco, Amazon.com

6 of 17 Courtesy of Rebecca Greenfield

The Entrepreneur

“Don’t spend a ton on black dresses. Even cheap ones can look expensive with the right accessories.”

Cotton-blend dress, $325, Rebecca Taylor, Rebeccataylor.com. Suede "Corinne" pumps, $177, Schutz, Madisonlosangeles.com. Leather "Astrid" Satchel, $348, Michael Michael Kors, 866-709-5677 for locations

7 of 17 Courtesy of Rebecca Greenfield

The Entrepreneur

“A well-tailored blazer exudes authority. Working in a male-dominated field, that’s essential.”

Viscose "Vicky" Blazer, $460, Sandro, Sandro-paris.com. Leather clutch, $520, Marni. Select Barneys New York, 888-8-BARNEYS

8 of 17 Courtesy of Rebecca Greenfield

The Financier

Corin Minier, financial analyst at Apollo Global Management, may work with a bunch of suits, but she wouldn’t be caught dead in an oxford shirt. (“They’re too boxy!” she says.) Softly tailored feminine pieces define her pretty—but polished—style.

“You don’t need a zillion pairs of heels. Nude ones match everything.”

"Karl" blazer, $465, Diane von Furstenberg, Dvf.com. Silk shirtdress, $295, Elizabeth and James, Shopbop.com. Snake-print pumps, $328, Kate Spade New York, Katespade.com. Leather tote, $348, Michael Michael Kors, 866-709-5677 for locations.

9 of 17 Courtesy of Rebecca Greenfield

The Financier

"If I can cinch it, I will -- a belt makes any outfit look more put-together."

Polyamide coat, $685, Sandro, Sandro-paris.com. Blouse, $198, Tommy Hilfiger, 212-223-1824. Skirt, $165, Lacoste.com. Earrings, $20, Absolute, Hsn.com. Gold-plated necklace, $70, Vanessamooney.com. Cuff, $20, Lydellnyc.com. Belt, $250, 3.1 Phillip Lim, 31philliplim.com. Pumps, $175, Joan and David. Select Nordstrom, 800-933-3365. Tote, $525, Z Spoke Zac Posen, Bloomingdales.com

10 of 17 Courtesy of Rebecca Greenfield