Dress Well at Any Age: The Right Way to Break Fashion Rules

When Traci Wolfe turned 50, she decided to celebrate all year long by tackling 50 new experiences and blogging about them. So far, she's tried knitting, yoga—and wearing miniskirts. "I love them, but a few years ago I decided I shouldn't wear them anymore," she says. "I was worried about people's reactions." Wolfe did a trial run at the beach and realized, "Short skirts make me feel hot!" Here, she pairs a flouncy cotton pointelle version with a sophisticated tweed jacket, silk camisole and T-strap heels for a look that's polished, not preteen.

To show off great legs:
Stick to modest tops. Try a jacket or button-down rather than a tee, tank, or low-cut blouse.

Think swingy. Wolfe's skirt is short, but it isn't tight, keeping the focus on her legs, not her rear.

Skirt, Catherine Malandrino, $245. Jacket, CH Carolina Herrera, $845. Camisole, Hy+Dot, $90, Necklaces, Daria de Koning. Bracelet, Joyce Makitalo. Heels, Sergio Rossi.

Andrea Fishkin, a sales superviser and stylist, spotted her first silver strand right before her Bat Mitzvah; by 18 she was entirely gray. "I fought back by dyeing it," she says. "I suffered all through my teens—I was so insecure about the slightest bit of roots showing." But seven years ago, Fishkin decided she was sick of all the upkeep. "I'm so much more comfortable with myself now, and I think that comes across," she says. "I used to wear all black, but that isn't me anymore." This teal gown plays up the contrast between Fishkin's striking gray waves and her calendar age, thanks to its sexy silhouette and vibrant color.

To complement gray hair:
Don't compete with it. When your hair makes an extreme statement, keep jewelry to a minimum. Glowing skin is your best accessory.

Add youthful touches. Fishkin's dress has a high slit, a plunging neckline, skinny straps, and a body-hugging shape.

Gown, Edition by Georges Chakra

As sales director for the NYC-based vintage store What Goes Around Comes Around, Jennifer McClain doesn't just wear the clothes, she lives the lifestyle: "My apartment is furnished with antiques, and I organize my closet by decade," she says. "I love playing dress-up every day." When looking to capture a specific era or style, the key is in the details, from the print on McClain's dress to her carefully coordinated jewelry, hat, belt, gloves, and shoes (What Goes Around Comes Around). "The '40s were a time when women could be comfortable but also look put-together," McClain says. "The dresses especially are kind to curves."

To go retro:
Start with small doses. You can pair vintage costume jewelry with jeans and a tee. Gradually work up to more pieces, like a scarf, hat, or skirt.

Pay attention to fabrics. Clothes from the '20s were often made of thin silk and tend not to preserve well. Later decades incorporated synthetics like rayon, which drape nicely. (Ignore sizing—a 14 then might be a 6 now.)

Cuff, The Family Jewels.

"When I hit menopause six years ago, I hardly recognized myself, even though I still felt young inside," says Sandra Alvim, an astrologer and the author of Yes, I'm 58! "I found a picture of me at 27 and decided if that's how I felt, then that's how I should look." Alvim changed her workout routine ("I do tons of push-ups") and got her former body back. This subtly sequined dress highlights her toned physique. Suede heels add a pop of color. "I dress with elegance and common sense. You don't have to look dowdy at 60," she says. "It feels great to be sexy."

To wear strapless:
Find conservative cuts. Balance exposed arms and shoulders with a knee-length dress.

Save color for your feet. Bright and strapless is overkill. Accessories are the place to go wild.

Dress, Sanchez by Angel Sanchez, $924. Heels, Edmundo Castillo. Earrings, Emily & Ashley. Ring, Anton Heunis.

"I know people say long hair can be aging, but I think mine keeps me young," says Diane Sheridan, a dance teacher and hairstylist who hasn't worn hers short since a disastrous cropped cut almost 40 years ago. She loves the wash-and-wear ease ("I can just put it up and go") and relishes her distinct look ("My grandkids show me off to their friends"). To play up her hair, Sheridan gravitates toward flowing, feminine pieces, like this chiffon maxidress. "You can never go wrong being who you are," she says.

To spotlight long hair:
Keep it in great condition. Sheridan uses a blow-dryer only on her roots for lift and lets the rest dry naturally. She avoids dyes, swears by natural bristle brushes, shampoos twice a week, and gets regular trims.

Choose bold jewelry. Earrings have to be large so they don't get lost in a tangle of hair. Keep bracelets, necklaces, and rings in proportion, too—nothing dainty.

Dress, Salvatore Ferragamo, $790. Earrings, Emily & Ashley. Cuff, Sushma Patel. Belt, Salvatore Ferragamo. Shoes, Edmundo Castillo.