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10 Stylish Ways to Break the Rules at 50+

Don’t let age limit your fashion options

(Left to right) Inès de La Fressange, Lisa Edelstein, Angela Bassett and Sharon Stone
(Left to right) Inès de La Fressange, Lisa Edelstein, Angela Bassett and Sharon Stone
Marc Piasecki/WireImage; VALERIE MACON/AFP via Getty Images; The Walt Disney Company via Getty Images; Arturo Holmes/Getty Images

Age has nothing to do with style. At least that’s what fashionable people appear to be saying as they flout the old over-50 rules. No need to mimic runway looks or get gaudy. All it takes is the confidence to wear on the outside how you feel on the inside. If you love color but live in neutrals, want to dazzle but not overwhelm or just wish you had the guts to look cooler, this column’s for you. Check out these rule-breaking celebs with the right idea. They ...

1. Wear leather all the time

(Left to right) Rita Moreno, Charlize Theron, Isabelle Huppert and Brooke Shields
(Left to right) Rita Moreno, Charlize Theron, Isabelle Huppert and Brooke Shields
Stefanie Keenan/Getty Images for Women in Film (WIF); Hollywood To You/Star Max/GC Images; Vittorio Zunino Celotto/Getty Images; TheStewartofNY/GC Images

A black leather moto jacket used to be a rebellious teenage emblem. Now it’s the first thing 50-plusers reach for when they want to be a little irreverent. Style-breakers have dialed up the cool effect by adding faux leather pants, dresses and skirts to their edgy options. Avoid going overboard on the “tough” look and choose classy timeless styles like pencil or midi skirts, shifts or sheaths that are devoid of studs, buckles or fringe (you can always add the latter in a bag or boots), or opt for a fashion color instead of black.

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2. Turn up the optics in prints

(Left to right) Maya Rudolph, Patricia Arquette, Loretta Devine and Gloria Estefan
(Left to right) Maya Rudolph, Patricia Arquette, Loretta Devine and Gloria Estefan
Jon Kopaloff/Getty Images; Jerod Harris/FilmMagic; Leon Bennett/Getty Images; Raymond Hall/GC Images

Rule-breakers are not into itsy-bitsy prints or muted preppy stripes. Instead, they choose can’t-miss animal prints, bold stripes, high-contrast menswear checks and splashy florals that turn simple silhouettes into head-turning looks. In fact, combining a wild print with a basic style is the key to success here. Animal prints like leopard or zebra in neutral colors are the easiest way to start slipping patterns into an existing neutral wardrobe. They quickly integrate with clothes you already own and have a sophisticated look you won’t tire of or regret.

3. Always add accessories

(Left to right) Diane Keaton, Susan Sarandon, Jeremy Irons and Matthew McConaughey
(Left to right) Diane Keaton, Susan Sarandon, Jeremy Irons and Matthew McConaughey
Michael Buckner/WWD via Getty Images; Jamie McCarthy/Getty Images for Christian Siriano; Karwai Tang/WireImage; Dan Istitene - Formula 1/Formula 1 via Getty Images

Some people never look boring even when they’re wearing the most casual outfit. That’s because they personalize it with accessories. It’s the first thing people notice and the one thing they remember about you. Though many women over 50 still wear “statement” necklaces and earrings (rather than low-key dainty chains and studs) for extra sizzle, sparkly hair accessories, elegantly wrapped or draped scarves, bold glasses and colorful shoes or boots have joined this category of add-ons. All are perfect last-minute, age-breaking extras that can spark a ho-hum closet back to life.

4. Wear updated jeans

(Left to right) Julianne Moore, Javier Bardem, Gina Gershon and Jennifer Garner
(Left to right) Julianne Moore, Javier Bardem, Gina Gershon and Jennifer Garner
Emma McIntyre/Getty Images; David Benito/WireImage; Michael Loccisano/Getty Images; Bellocqimages/Bauer-Griffin/GC Images

Almost everyone over 50 has old jeans that are broken in just right. But the most stylish jeans-wearers don’t stop there. Each year they freshen their denim stash with on-trend proportions, fits and washes that say, “I know what’s in fashion.” Style-seeking men and women are wearing straight-leg jeans with a high rise and relaxed fit, though some women are taking the trendiness up a notch with wide-leg jeans. It’s an affordable way to look brand new, and Gap, Old Navy and H&M all offer low-cost versions. Stick to vintage-look washes, black or soft medium blues for the coolest effect.

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5. Take some fashion risks

(Left to right) Drew Barrymore, Will Packer and Heidi Klum
(Left to right) Drew Barrymore, Will Packer and Heidi Klum
Gotham/FilmMagic; Kate Green/Getty Images for Universal; Hollywood To You/Star Max/GC Images

Extreme fashion is not for the fainthearted. However, adding just one over-the-top item can turn a fairly predictable outfit into a scene stealer. Look for bomber jackets, dramatic dusters or bold trench and maxi coats to make a memorable entrance or exit and add a pulled-together posh look to whatever lies beneath.

6. Make a hair statement

(Clockwise from top left) Winona Ryder, Janet Jackson, Halle Berry, Hiroyuki Sanada, Herbert Bohanon and Guy Fieri
(Clockwise from top left) Winona Ryder, Janet Jackson, Halle Berry, Hiroyuki Sanada, Herbert Bohanon and Guy Fieri
Roy Rochlin/Getty Images; Edward Berthelot/Getty Images; Michael Kovac/Getty Images for Champagne Collet & OBC Wines; Albert L. Ortega/Getty Images; Unique Nicole/Getty Images; Scott Dudelson/Getty Images for Stagecoach

Red lipstick has always been a favorite way for mature women to grab attention. Nowadays amped-up hair is the way to go for men and women over 50. It creates a signature look (or at least an eye-catching one) and makes whatever you wear — from a suit to joggers and T-shirt — look more stylish. Try shaggy layers, textured spikes, two-tone color, extensions and hairpieces (who cares if it’s obviously fake?). If you’re a man with a full head of hair at 50, a silvery ponytail can be amazing.

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7. Flash a little skin

(Left to right) Jennifer Lopez, Mariska Hargitay, Salma Hayek and Nia Long
(Left to right) Jennifer Lopez, Mariska Hargitay, Salma Hayek and Nia Long
Bellocqimages/Bauer-Griffin/GC Images; Roy Rochlin/Getty Images; John Phillips/Getty Images for BFI; David Livingston/FilmMagic

Thigh-baring skirts, plunging necklines and midriff-revealing tops are usually seen as “trying too hard” to look young. Some women over 50 can dive right in and fearlessly wear all of the above. More discreet toe-in-the-water types can take it slow by adding more sleeveless or off-the-shoulder tops and dresses and braving bare legs with boots and booties. The key here is to bare one spot at a time. Legs or shoulders, for example — not both. It’s also good incentive to get back into an exercise and body care routine.

8. Mix casual and dressy

(Left to right) Stanley Tucci, Maye Musk, Debra Messing and Howie Mandel
(Left to right) Stanley Tucci, Maye Musk, Debra Messing and Howie Mandel
Shane Anthony Sinclair/Getty Images; Marc Piasecki/Getty Images For Roger Vivier; Monica Schipper/Getty Images for Netflix; Steve Granitz/WireImage

Combining tailored clothes with T-shirts and sneakers, casual clothes with sparkly earrings and a fancy bag or good leather shoes shows creativity. This strategy expands your wardrobe and gives seasonal items a year-round life. It’s also a great way to repurpose seldom worn tailored or “evening” pieces and jewelry to spark everyday jeans, skirts or dresses. The opposite works too. Pair sneakers or chunky comfort sandals with work clothes and evening attire, “good” leather boots and shoes with jeans and leggings.

9. Buy red, pink or green, not black

(Left to right) Brad Pitt, Kim Cattrall, Jean Smart and Sofía Vergara
(Left to right) Brad Pitt, Kim Cattrall, Jean Smart and Sofía Vergara
Axelle/Bauer-Griffin/FilmMagic; Araya Doheny/FilmMagic; Jon Kopaloff/FilmMagic for HBO; MEGA/GC Images

Many stylish older women and a few spotlight-seeking guys have shifted away from neutrals and into a rainbow of color. A jolt of color adds personality and fresh energy to any wardrobe and brings out the glow in mature skin. Shades of green from neon to emerald and lime, bright pink, vibrant red and shimmery metallics are fabulous, not flashy. Go head-to-toe for extra dazzle, though wearing one technicolor piece is all you need to be conspicuous. Start with a stack of tees, one brilliant blazer or a vibrant scarf for a test drive.

10. Show their shape, whatever it is

(Left to right) Holly Robinson Peete, Christie Brinkley, Jennifer Coolidge and Eva Longoria
(Left to right) Holly Robinson Peete, Christie Brinkley, Jennifer Coolidge and Eva Longoria
Theo Wargo/Getty Images for NYFW: The Shows; Raymond Hall/GC Images; JC Olivera/FilmMagic; Rachpoot/Bauer-Griffin/GC Images

“Body positivity” is the new motto of style shakers and breakers over 50 who wear clingy dresses and body-hugging leggings. Not long ago grownup women dieted rigorously to fit into their clothes, wedged themselves into shape wear or wore loose dresses and layers as antidotes to aging apple- or pear-shaped bodies. Forget that! Today there is the freedom to wear what you love and strut your stuff whatever your size and shape. Let’s all embrace it.