Simone Tobias Stilettos were the norm for this self-proclaimed girlie girl. “I wasn’t comfortable unless I was in heels, a formfitting dress, and dramatic makeup,” says the creative director of a men’s clothing company. That all changed the day the 36-year-old fell in love with a pair of very unfeminine oxford flats. Since then Simone has picked up four more menswear styles and insists that she has never felt sexier: “I like the idea of wearing something ‘borrowed from his closet.’ ”
To buy: The Generic Man canvas oxfords. Milly blouse. Banana Republic trousers. Timex watch. Nugaard Design bracelet.
2 of 5Poppy de Villeneuve
Fashion Risk: A Sequin Skirt
Elan Carter After having her second child, Elan found motivation to get back to her prebaby size in an unlikely place: a stunning sequin skirt. But even after she lost the weight, the stay-at-home mom remained reluctant about such a look-at-me piece. Once she slipped it on, however, she realized, “it didn’t matter that my stomach wasn’t as flat as it used to be, since the sequins drew attention to my legs, my best feature.” By pairing the skirt with flats and a basic tank, Elan keeps it from looking too dressy or “hoochie mama—it’s fun and polished at the same time.”
To buy: Tory Burch sequin skirt. Club Monaco top. French Sole flats. Kenneth Jay Lane bracelets.
3 of 5Poppy de Villeneuve
Fashion Risk: A Jersey Dress
Claudia Gerola Once Claudia became an empty nester, she wanted a change from the jeans-and-khakis routine of a Connecticut mother of two. So the executive consultant picked up and moved to New York City. After that, trying on a stretchy jersey dress at the urging of her daughter didn’t seem so daunting. The forgiving print, soft draping, and not-too-slinky cut dispelled any doubts. “I feel feminine and confident,” says Claudia. “The dress says, ’I’m in my 50s, and I look good!’ Not ’I’m in my 50s, trying to look 30.’ ”
To buy: Diane von Furstenberg silk-jersey dress. Kenneth Cole New York heels. Coach bag. R. J. Graziano earrings. Ippolita bracelets. Beyond Rings ring.
4 of 5Poppy de Villeneuve
Fashion Risk: An Eye-Catching Tunic
Alix Liiv In a city where black is everyone’s favorite color, stepping out in a bright print seemed foreign for this born-and-bred (and likewise black-obsessed) New Yorker. So when a friend of Alix’s gave her a vibrant tunic from India, it sat unworn in her closet for months, until the day the 27-year-old events manager needed a pick-me-up. “When I wear it, I can’t help but exude positive energy,” says Alix, who now tries to inject color into all her outfits. “It makes people notice me—and who doesn’t want some attention now and then?”
To buy: Tolani silk tunic. Levi's jeans. Kelsi Dagger wedges. Kooba bag. Allison Daniel Designs earrings. Kenneth Jay Lane bracelet. Kanupriya Jewelry ring.
5 of 5Poppy de Villeneuve
Fashion Risk: Skinny Jeans
Natascia Ayers Only the love of her new knee-high boots could convince curvy, five-foot-three Natascia to get into skinny jeans. The 40-year-old attorney wanted to wear jeans tucked into her boots, and therefore they had to be slim. So Natascia tugged on countless styles until she found the perfect pair. The thick denim doesn’t reveal every bump, the 2 percent stretch fits her contours, and the dark rinse elongates her petite frame. (Their under-$30 price tag didn’t hurt, either.) “They may be called skinny, but you don’t have to be a stick to wear them,” she says.
To buy: Uniqlo jeans. Elizabeth and James blazer. Calvin Klein top. Nine West heels. Skinny ring.