Denise Hueglin, 61
The rut: "My daughter says I dress like a man," says Hueglin, who wears a uniform for her work as a mail carrier and in her off-hours sticks to cargo pants, hoodies, and work boots. "I don't feel comfortable with my broad shoulders or my stomach," she explains. "I don't want to draw attention to them."
The rescue: To show off Hueglin's terrific legs, O's creative director, Adam Glassman, puts her in a knee-length stretch jersey dress that's sexy, not revealing. Ruching across the stomach visually slims her waist. "This makes me realize there are things I can wear at my age that aren't dowdy," says Hueglin. A layered cut and blow-out by Dominick Pucciarello of Mizu New York finishes the look.
To boost the femininity factor:
- A jersey dress is always appropriate—and less work than pairing separates.
- Look for V-neck silhouettes and side ruching, which play up curves.
- Accessories—colorful shoes, distinctive jewelry—are the easiest way to soften your style.
Dress, Max Mara, $695. Earrings, Badgley Mischka. Necklace, Made Her Think. Ring, Wendy Mink Jewelry. Shoes, Christian Louboutin.
Angela Butler, 42
The rut: Because Butler works as a banker, her wardrobe is limited to conservative black suits, pencil skirts, and cardigans (she does have one gray suit). The upside? It takes her "seconds to get dressed in the morning." But "I feel like I could express myself more through clothing," she says.
The rescue: Straight, dark hair and monotone clothes make Butler look unintentionally severe, so we lighten things up: Pucciarello gives her a softer, layered bob, while Glassman prescribes dark, jewel-tone separates in small doses—a blue pleated silk skirt and drapey blazer over a floral-printed tank. The result is pulled together but much more youthful and modern than what Butler was used to. "I like navy and purple!" she says.
To incorporate more color into your wardrobe:
- Choose pieces in rich, complementary shades—a matching suit tends to make you look years older.
- Balance a boldly patterned top with a black blazer.
- Illuminate your face by adding a silver or gold necklace.
Skirt, Etro, $885. Blazer, Loft, $90. Tank, Elie Tahari, $248. Earrings, Kara Ackerman. Necklace, Rebecca. Watch, Philip Stein. Ring, Maud Jewelry. Shoes, Fratelli Rossetti.
Shannon Bumgarner, 39
The rut: A stay-at-home mother of two young boys, Bumgarner lives in baggy tees and sweatshirts—most dating to the 1990s—to hide her ample chest, a part of her body she's sensitive about. "I'm afraid that if I wear something clingy when I'm only going to the bus stop, people will think I'm trying to flaunt my figure," she says.
To flatter a busty figure:
- Avoid oversize tops, which bring attention to your chest and make you look bigger overall.
- Show some skin. A V-neck elongates your torso and draws the eye upward to your face.
- Stick to shirts with some stretch in the fabric (this goes for button-downs, too), which won't pull or gape at the bust.
Top, M Marc Bouwer for QVC, $39. Pants, Magaschoni, $598. Bangles, Noir Jewelry and Georg Jensen. Shoes, Christian Louboutin.
Jill DeBernardis, 50
The rut: DeBernardis, a volunteer with a charitable foundation, admits to falling back on age-inappropriate velour tracksuits (she estimates she owns at least 12) in candy colors, often bearing trendy slogans. She blames the comfort factor. "I don't need to be coordinated and made-up during the week," she says. "I'm in that in-between stage of life: I'm not ready to be my mother, but I shouldn't be dressing like my daughter, either."
The rescue: Pucciarello gives DeBernardis a shorter, more flattering cut, bringing her hair off her face to highlight her cheekbones. Glassman replaces her sweats ("After a certain age, you should not be wearing Barbie pink") with slimming, neutral corduroys and a T-shirt in stand-out citrus green. A leather trench is a grown-up, well-priced staple DeBernardis can wear for years, to the grocery store or out to dinner.
To graduate from sweats:
- Stretch corduroys are as comfortable as drawstring pants but can get you through a PTA meeting, a carpool, or a lunch date.
- Invest in a versatile trenchcoat in gray or khaki to give polish to your casual daytime look.
- Consider putting on proper pants and a shirt, even if you work from home. You'll feel more motivated—and inspired to do it each day.
Corduroys, J.Crew, $80. T-shirt, Lilla P., $58. Trench, Banana Republic Heritage, $398. Earrings, Julie Collection. Bracelets, Bounkit. Belt, LAI. Watch, Tag Heuer. Shoes, Musette.
La Toya Lewis
The rut: Lewis, an opera singer, has yet to take off the pounds she put on in college, and she's mostly avoided shopping for her current shape. "I always thought, I'll buy clothes when I lose weight," she explains, "but I never did." Her shirts are snug ("If it fits my stomach, it doesn't fit in the arms") or unflatteringly cut ("Turtlenecks are the easiest thing to find"), and she often resorts to the same old pair of black pants. "I need to look nice for all the auditions I go on, but I have no idea how to get there," says Lewis.
The rescue: A stretch cotton shirtdress has enough give for Lewis's figure—it skims over curves rather than encasing them. The bright, solid color has a lengthening effect; the thick belt cinches Lewis at her narrowest. Pucciarello gives Lewis "big, fun, sexy hair"—all that height and volume elongate her round face. The result: She's confident about nailing her next audition. "If I look good, then I feel at ease," she says.
To suit a curvy frame:
- A dress with stretch slims without highlighting imperfections, as separates tend to do.
- A belt worn high on the waist gives the illusion of longer legs.
- Skirts that cover the kneecap emphasize the slenderest part of the leg.
Shirtdress, Boss, $495. Belt, Adrienne Vittadini. Earrings, Kara Ackerman. Necklace, Mark Davis for Monique Péan. Bracelet, Sibilia. Ring, Marcia Moran. Shoes, Gucci.
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