Melissa Skoog

It's 2009! Take a deep breath and blow off your old fashion rules. Pick a bold style; test a new shape; dabble in color. Here, six women who dared. 

"A new business requires a new image."

"I used to dress in head-to-toe Prada," says Melissa Skoog, 35, of her years as vice president of public relations for the iconic label. Sounds like every woman's fantasy—except that the designer uniform left no room for her own taste. Skoog's new project—as partner in an online style magazine (, launching next month) and co-founder of an e-commerce site (, going live in June)—is allowing her to "find my fashion voice again. Since we're meeting investors, I need to look really put together." But don't think that Skoog has to wear nothing but high-end labels: This svelte herringbone sheath is amazingly well priced (Talbots, $158), while the cable-knit cardigan (Ralph Lauren Black Label, $655) is a softer stand-in for a jacket. Unmatched pieces aren't as foolproof as a suit, but the effect is fresher, more contemporary. The serious neutrals are balanced by the two shots of bright purple (sweater and shoes); a belt (J.Crew) adds shape and polish. 

Earrings, Irene Neuwirth; bracelet, House of Lavande Vintage; bag, Sang A. Shoes, Dior

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Alexandra Wentworth

2. "This year I'm warming up to bright color."
"I have two lives, and two wardrobes," says actress-comedian Alexandra Wentworth, 43. For on-air appearances—as a Hollywood shrink on Head Case, an unscripted comedy on Starz, and as a regular contributor on Oprah Fridays Live—she needs "color that pops," like bright blue or emerald. At home with husband George Stephanopoulos, the ABC News correspondent, and their two children, she says, "I gravitate toward black and steel gray. I don't like to be showy." Wentworth's pink-loving, princess-minded daughters would like her to brighten up. "Last New Year's, my 6-year-old made me buy fuchsia suede pumps for a party, and I never got so many compliments in my life." Vivid shoes, like the yellow satin sandals here (Christian Louboutin), are a good way to start adding color, she says—"then work your way up." Says Wentworth of these orange pants (J.Crew, $98) and purple silk moire taffeta tie-neck blouse (L'Wren Scott, $1,300): "It's fun and chic. I'd never have thought of putting these two colors together, so I'm learning!"

Bracelets, Fred Leighton; ring, Yossi Harari
Elaine Griffin

3. "This year I'm switching from preppie to sexy."
"I was hiding behind my weight," says Elaine Griffin, 44, a Harlem-based interior designer whose book, Design Rules, will be published this fall. "I didn't want to think about the messy things in life, like relationships: For eight years I did nothing but work and eat, eat and work. My blood pressure skyrocketed and my doctor told me diabetes was on the horizon." So she lost 50 pounds, going from a size 14 to a size 6. Serendipitously, once she slimmed down, a wonderful man showed up—and the Georgia-born Griffin began questioning whether her lifelong Southern prep style ("Lilly Pulitzer in summer, cords and turtlenecks in winter") was alluring enough. She wasn't about to do a va-va-voom fashion number, but what she needed was a decorous everyday version of sexy: a filmy ruffled blouse (Luisa Beccaria, $1,335) with just a glimpse of color-matched bra (Conturelle, $115) and a shapely pencil skirt that comes discreetly to the knee (Newport News, $29). "I'm a little less nervous now about wearing revealing clothes," Griffin says. "I can be sexy but still a lady." 

Earrings, House of Lavande Vintage; belt, GF Ferre; bracelet, Kimberly McDonald; shoes, Diego Dolcini
Kendall Conrad

4. "This year I'm playing with prints."
"I love prints on other people," says Santa Barbara–based handbag designer Kendall Conrad, 42. "But I have no time to figure out how to do them right." Undemanding solid colors are more like it; her daily wardrobe consists of no-brainer pants, tanks, and sweaters, or simple linen dresses. Then she spotted this neo-hippie top and skirt (Gregory Parkinson, $505 and $975): "It's young and sexy and bohemian. Sometimes prints can look prim and uptight, but these are groovy." They also illustrate two basic takes on pattern mixing: the same motif in two different colors (pink for the skirt, blue for the sleeves), or two different motifs in the same colors (the bodice and sleeves of the top). Although Conrad thought a busy print might rule out accessories, the patterned fabric proved compatible with some of her favorite things: hoop earrings (Me&Ro), bangles (Me&Ro; Citrine by the Stones), flat sandals (Giuseppe Zanotti Design), and her own Kendall Conrad leather bag (this tote is from her Country/Beach Collection). The fur she's lounging on, by the way, is totally faux. 

Necklace, House of Lavande Vintage; belt, Melamed
Nicholle Francis Mena

5. "This year I want to play up my curves."
"Thank goodness for Spanx!" says 36-year-old dietitian Nicholle Francis Mena as she slips into a beautifully cut jersey sheath (David Meister, $285)—a total contrast to the boxy wardrobe she used to take refuge in. "I've always wanted to wear a red dress," she admits, "but I'd say to myself, 'I can't do that! That's not me!'" Describing herself as "that big, tall girl who always stood out," Mena, a size 12, says she deflected attention by wearing darker, looser clothes—"nothing formfitting." But since giving birth to 2-year-old Simone, she's more comfortable with her voluptuous body: "When you get older, you start to accept yourself instead of always wishing you looked different." The great thing about this dress is that it's sensuous, yet not a bit risqué. The crossover bodice emphasizes—tastefully—Mena's cleavage; the raised waist makes her legs look longer; and the arm coverage minimizes broad "linebacker" shoulders, making her feel less self-conscious. "Long sleeves are a bit of a security blanket for me," she says. "Like wearing a T-shirt over your swimsuit." 

Earrings, Kara Ross; ring, Replica for Jennifer Miller; shoes, Lauren by Ralph Lauren
Liseanne Frankfurt

6. "This year I'm bargain hunting."
"I just bought a $30 cardigan!" says California jewelry designer Liseanne Frankfurt, 37, who was a stranger to lower-priced stores until her then 6-year-old daughter started dragging her into Zara, H&M, and J.Crew. Now she views mass fashion with new eyes: She was awed, for example, by the feel-good fabric ("Texture is important to me"), excellent fit, and up-to-date shape of this smart little suit (Express blazer, $148, and skirt, $70) and sheer top (Gap, $58). Although Frankfurt runs a luxury business, she is neither a label snob nor a major splurger ("I invest in pieces that last; I don't buy for one season and then pack it off to the resale shop"). So she thinks it's an inspired strategy to mix affordable clothes with high-end accessories like knockout patent leather shoes (Manolo Blahnik) and her own 18kt-gold bracelets, rings, and earrings (all, LFrank). "If you're wearing good jewelry," she says, "no one will question where your suit came from." 

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