Jessica Vertullo Maher

Photo: Sergio Kurhajec

Evening
Standing 6'2" since age 13, former Division I college volleyball player Jessica Vertullo Maher, 36, has learned to appreciate her tall, broad-shouldered physique. But now that she's a real estate agent with formal work events to attend, she finds herself playing it safe with evening wear: "I usually limit myself to basic black cocktail dresses," Maher says. This bright, slinky silk dress is a flattering new option. The halter neckline draws attention up to Maher's face rather than out toward her shoulders; the sleek fit and solid color keep the look from feeling fussy.
Dress, Issa, $714, shopbop.com. Earrings, Kendra Scott, $85, charmandchain.com. Ring, David Yurman, $4,500, davidyurman.com. Shoes, René Caovilla, $895, Neiman Marcus, 800-365-7989.
Zakiya Proctor

Photo: Sergio Kurhajec

Weekends
When 5'4" Zakiya Proctor played college basketball, her taller teammates assumed she had no shopping issues. "But I've never been able to find clothes that are small enough in the waist and big enough everywhere else," says Proctor, 31, now studying to be a physician's assistant. Her blouse tackles this problem with hidden buttons and stretch fabric. Fitted jeans also conform to her shape.
Shirt, The Shirt by Rochelle Behrens, $88, $88, the-shirt.com. Pants, James Jeans, $123, Mercantile, Portland, 503-223-6649. Necklace, Roxanne Assoulin for Lee Angel, $180, leeangel.com. Ring, Noir Jewelry, $140, noirjewelry.com. Belt, Gap. Shoes, Talbots, $149, talbots.com.
Samantha Carey

Photo: Sergio Kurhajec

Weekends
Like Proctor, executive search consultant Samantha Carey, 38, struggles to find clothes that work with her upper body. "I used to buy jackets and have them taken in four sizes at the midsection," Carey says of her days as a competitive swimmer. This silk jersey dress skims Carey's shoulders while emphasizing her waist. "I've always felt unsure about what to wear outside the office or gym," says Carey. "This is a perfect solution."
Dress, Aidan Mattox, $255, edressme.com. Earrings, Irene Neuwirth, $7,770, ylang23.com. Bangles, BaubleBar, starting at $36 each, baublebar.com.
Delissa Reynolds-Lyssy

Photo: Sergio Kurhajec

Office Casual
Delissa Reynolds-Lyssy, 49, follows a weekly yoga and running routine. But what really keeps her fit is her job: She owns a bar, and "carrying around cases of beer is a serious workout!" Reynolds-Lyssy needs a wardrobe that can go from the office, where she handles administrative work, straight to serving patrons at night. These wide-leg pants flatter her hips and thighs. The sheer blouse, with its delicate fabric and print, softens Reynolds-Lyssy's sculpted top half.
Pants, Adam, $225, shopadam.com. Blouse, Gap, $50, gap.com. Earrings, Me & Ro, $940, meandrojewelry.com. Bracelets, Kaur Collection, $85 for set of ten, , Kenneth Jay Lane, starting at $63, 877-953-5264, Gorjana, $90, gorjana.com. Shoes, Fratelli Rossetti, $540, 212-888-5107.
Rachel Roosevelt

Photo: Sergio Kurhajec

Suited Up
"Downhill racers tend to be the heftiest skiers," says Rachel Roosevelt, 27, a member of the U.S. Ski Team from 2000 to 2004 who has the sturdy, straight-waisted body to show for it. Roosevelt, now a macroeconomic researcher, still feels like an amateur when it comes to dressing for the corporate world. Because of her muscular legs, she says, "tight skirts tend to bunch on me." Problem solved: Choose one with some stretch. The high-contrast stripes carve out Roosevelt's figure, creating an instant hourglass. The waist-accentuating peplum and rounded shoulders of the jacket exaggerate existing curves.
Skirt, Michael Michael Kors, $100, 866-709-5677. Jacket, L.K.Bennett, $545, lkbennett.com. Earrings, Noir Jewelry, $215, noirjewelry.com. Belt, Kenneth Cole New York, $58, kennethcole.com. Shoes, Aldo, $70, aldoshoes.com.

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