Olivia Chantecaille

Uptown Florals
Olivia Chantecaille, 34, creative director, Chantecaille Beauté

"Color is my passion. I'm surrounded by it," says the cosmetics executive, who fell in love with this ruffled floral wrap dress (Chadwick's, $60) and equally charming pink shoes (Guess by Marciano, $99). "My whole spring makeup line is about blues, so this print is very on-trend." Since looks are her business—Olivia co-founded Chantecaille Beauté with her mother, Sylvie, who created Prescriptives for Estée Lauder—she has acute style radar, and she thinks inexpensive clothes are much more fashion-savvy than they used to be ("I always pop into Zara because they're quick to get runway styles into the stores"). Another thrifty approach is to dig forgotten pieces out of her closet and "figure out how to wear them in a more modern way." Olivia is into jewelry ("Maybe I designed it in a past life?"), and she was smitten with these burnished pieces: a lock-shaped pendant necklace (Victoria's Secret, $38) and a big, flowery ring (Kenneth Jay Lane, $37). 

Dress: $60.00

Shoes: $99.00

Necklace: $38.00

Ring: $37.00
Total: $234.00

Julie Macklowe


Downtown Denim
Julie Macklowe, 31, investment banker and founder of Macklowe Asset Management

"Glamorous with a little edge is the look I go for," says Julie, whose buttoned-up work style segues into "hedge-fund rocker chick" on weekends or at night. That's why she took to the skinny jeans from Express ($59.50)—"Without seeing the label, I couldn't tell them from a higher-priced pair"—and a sexy Flashdance-esque fringed top (H&M, $17). For fashion bargains, Julie likes eBay; for jewelry she's all about statement pieces like Bakelite necklaces, large rings—or this long necklace with trendy horn charms (Rimistyle, $20). Given the stratospheric prices of designer shoes and bags, it's nice to find some real steals: a chunky chain-strap purse (Hayden-Harnett for Target, $45) and vintage-inspired peep-toes (Chinese Laundry, $79). Attention, 40-plus shoppers: Don't ignore sources like Express (excellent for pants) or H&M (a terrific place to check out trends); their marketing may emphasize youth culture, but you'll find grown-up clothes there too. 

Jeans: $59.50

Top: $17.00

Necklace: $20.00

Purse: $45.00

Heels: $79.00
Total: $220.50

Carolyne Roehm

Mix Master
Carolyne Roehm, 57, lifestyle expert and head of her online company, Presentations

"The cheapest way to redecorate a room is to move the furniture around. The same goes for clothes," says Carolyne, who applies her trademark flair to everything from flowers to food, gift wrap to interiors. Recently she picked up some fabulous clothes at the Japanese chain Uniqlo, known for its cool, inexpensive sweaters—like the chic "boyfriend" cardigan she's wearing here ($49.50). "The colors are wonderful, and my splurge didn't cost an arm and a leg," she says. Although tank tops are one category you can always buy cheaply (Aerie by American Eagle Outfitters, $15.50), pants can be trickier if, like Carolyne, you're fussy about fit. But she was crazy about these wide-leg, high-waisted trousers with a "power mesh" liner for smoothing and support (Shape Fx, $59). A huge accessories fan, she liked the "shock" of yellow shoes (LifeStride, $35) and a vibrant flowered scarf (Old Navy, $12.50), plus richly textured hammered metal hoops (A.N.A. by JCPenney, $15). 

Cardigan: $49.50

Tank top: $15.50

Trousers: $59.00

Slingbacks: $35.00

Scarf: $12.50

Earrings: $15.00
Total: $186.50

Tinsley Mortimer

Modern Romantic
Tinsley Mortimer, 33, designer

"A ruffle gets me excited," says this New York woman-about-town, who designs handbags and clothes for a Japanese company and had a Dior lipstick color named after her (Tinsley Pink). "I'm happier in skirts and girly clothes than in jeans," she says. That's why she's excited about spring fashion's emphasis on quintessentially feminine styles like this one-shoulder jersey flounce dress (Donna Morgan, $140; the neon green belt is included): "The drapey, slinky fabric falls nicely on me," she says. Although Tinsley checks out stores like H&M, Urban Outfitters, and Old Navy for fun costume jewelry, T-shirts, or tanks, she usually has more of an investment philosophy about bags and shoes ("It's hard to get around the quality of the leather"). So she was stunned by the price ($69) of these gorgeous tricolor patent leather and satin pumps from Chinese Laundry, a company that's been making cute, affordable shoes for more than 25 years.
Dress and belt: $140.00

Pumps: $69.00
Total: $209.00
Malaak Compton-Rock

Laid-Back Layers
Malaak Compton-Rock, 30s, supporter of humanitarian causes such as hurricane relief and breast cancer research

"I fund things for a living, so I know how to shop smart," says Malaak, who combines roles as a carpooling mother of two (she's married to comedian Chris Rock) and founder-director of the Angel Rock Project, an online company that promotes volunteerism and social responsibility. She's an Internet-shopping enthusiast—ShopBop.com, Bluefly.com—and loves superstores like Gap or Target ("Why spend a ton of money on jeans or a tee?"). Malaak's favorite strategy is casual layering, epitomized here by a tank and jeans (Old Navy, $34.50) spiced with bold earrings (Rimistyle, $20) and a hot pink anorak. The jacket ($120) is from London Fog, of all places—it's no longer limited to Dad's beige trench—and the tissue-cotton, silk-hemmed tank is from J.Crew ($58), a consistently chic and accessible label that topped almost everyone's favorites list. 

Jeans: $34.50

Earrings: $20.00

Anorak: $120.00

Tank top: $58.00
Total: $232.50

Carolyne Roehm

Park Avenue Patterns
Carolyne Roehm

"It requires no imagination to dress in head-to-toe designer," says Carolyne. "How you mix high and low is the fun part." In her ninth book, A Passion for Blue & White, she shows antique china alongside reproductions "made in Taiwan yesterday," and she doesn't hesitate to stack up an inexpensive link bracelet with an expensive cuff. Even better is a high-society look in which everything is low priced, starting with a sheath (AB Studio, $59) that suits Carolyne's pared-down style perfectly. And there's cash to spare for a patent leather belt (Hobo International, $48) and bright heels (Colin Stuart for Victoria's Secret Catalog, $53), plus gold-tone jewelry (earrings, The Limited, $16.50; cuff, Kenneth Jay Lane, $45). 

Sheath: $59.00

Belt: $48.00

Heels: $53.00

Earrings: $16.50

Cuff: $45.00
Total: $221.50

Jaci Reid

The New Power Suit
Jaci Reid, 46, managing director, Westin Rinehart branding/communications firm

Washington power couples don't get much more forceful than Jaci and her husband, Morris: As "the charity arm" of their lobbying and communications company, she has a host of meetings and events to look good for, so her clothes need to work overtime. And here, conveniently, is the definitive office-to-evening outfit: a sesame-colored stretch-cotton jacket from Talbots ($164 online exclusive with code OPRAH) and a red jersey shirtwaist dress that delivers designer fashion for little more than the price of a movie ticket (Norma Kamali for Wal-Mart, $20). She's carrying an oversize clutch with the look of real croc (JCPenney, $20), and her slim, elegant legs seem even longer in skin-tone sandals (Abaeté for Payless, $38). Jaci's prime hunting grounds for inexpensive staples and accessories such as shoes, bags, and beads include K-Mart, TJ Maxx, Mango, and, for scarves, her friendly neighborhood street vendor.
Jacket: $164.00

Dress: $20.00

Clutch: $20.00

Sandals: $38.00
Total: $242.00
Tinsley Mortimer

Office Polish
Tinsley Mortimer

"I want one in every color!" says Tinsley of this soft, easy cardigan (Express, $34.50)—an upbeat alternative to a work blazer as well as a perfect, packable traveling companion. She also adores the way metallic trim dresses up the black tank (Victoria's Secret, $18). You can wear lightweight cotton knits right this minute if you layer them—they're truly multiseasonal. The hint of sparkle in the top echoes her sculpted silvery hoops (The Limited, $16.50) and gunmetal bangles (Loulou de la Falaise, $50 for three). And this isn't just any old pencil skirt: The wide, contoured waistband and off-center front slit make it look fresh off a very fancy runway (Express, $69.50). 

Cardigan: $34.50

Tank top: $18.00

Earrings: $16.50

Bangles: $50.00

Skirt: $69.50
Total: $188.50