10 Trendsetting Elderly Style Icons

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Both outrageously funny, pioneering, and strikingly stylish, Phyllis Diller and Helen Gurley Brown are two “glam-mas” that are very much missed. While the Cosmo editor-in-chief opted for shrewd sophistication over Diller’s exaggerated, gaudy glamour, the groundbreaking duo made bold style statements that exceeded mere fashion, up until their final days. They owned their look through and through, and we’ve selected a group of golden girls that match Diller and Brown’s trendsetting sensibility. Click through for a look at a few of our favorite age-defying style icons.

Helen Mirren

Naturally beautiful and effortlessly sexy, 67-year-old Oscar-winning actress Helen Mirren doesn’t always fuss with age-appropriate fashion. She’s never one to shy away from taking style risks, but she remains sophisticated and glamorous whether in Michael Kors or nothing at all. Just ask New York Magazine who recently did a nude photo shoot with the quietly edgy and versatile Mirren in a bathtub. “I’m still the good girl who wants to be a bad girl,” she confessed.

William S. Burroughs

The original hipster, Burroughs was wearing knit scarves and fedoras before Urban Outfitters could turn a fast buck. The cult figure’s funereal fashions consisted of dark suits, heavy glasses, a smattering of argyle, and a tie that often resembled a noose. Burroughs was heroin chic before the ‘90s made it famous. Ginsberg and Kerouac were other Beats with admirable style, but the Pope of Dope rocked his famous get-up like no one else could, right into his twilight years.

Zelda Kaplan

New York nightclub fixture and fashion maven Zelda Kaplan passed away earlier this year. Her dramatic exit from this mortal coil was befitting of the bold style icon she was right up to her mid-90s. She collapsed during the Joanna Mastroianni fashion show and never recovered. Her lively spirit translated to her trademark oversized glasses, African-print dresses, and tall hats. She was even a MAC Cosmetics’ poster girl. In 2010 she told New York Magazine that her bedtime was between midnight and 7AM. The socialite always said, “Live, live, live and have fun,” and her colorful polish proved it.

John Waters

Director John Waters recently accepted the CFDA Fashion Icon prize for Johnny Depp, but the Pink Flamingos filmmaker deserves some style recognition too — for the mustache and the suits, alone. His cinematic love affair with Mink Stole and Divine reveals his appreciation for original and outlandish style makers, but we’ve previously highlighted Waters’ fondness for freaky fashion apart from his on-screen muses:

“You don’t need fashion designers when you are young. Have faith in your own bad taste. Buy the cheapest thing in your local thrift shop — the clothes that are freshly out of style with even the hippest people a few years older than you. Get on the fashion nerves of your peers, not your parents — that is the key to fashion leadership. Ill-fitting is always stylish. But be more creative — wear your clothes inside out, backward, upside down. Throw bleach in a load of colored laundry. Follow the exact opposite of the dry cleaning instructions inside the clothes that cost the most in your thrift shop. Don’t wear jewelry — stick Band-Aids on your wrists or make a necklace out of them. Wear Scotch tape on the side of your face like a bad face-life attempt. Mismatch your shoes. Best yet, do as Mink Stole used to do: go to the thrift store the day after Halloween, when the children’s trick-or-treat costumes are on sale, buy one, and wear it as your uniform of defiance.”

Yoko Ono

To many, she’s the woman who allegedly broke up The Beatles, but Yoko Ono is an international style icon. Young Yoko sported wild hair, floppy hats, and baggy chic. Older Yoko is just as savvy. She’s a monochromatic, tailored goddess in dark shades and jackets, with an unaffected elegance people half her age have trouble pulling off.

Gloria Vanderbilt

We love her for designer jeans and raising silver fox Anderson Cooper, but Gloria Vanderbilt is a fashion diva with duality. She manages to simultaneously exude old guard sophistication and unfussy appeal. “To define yourself is like trying to bite your own teeth,” the always confident and pulled together socialite recently said of her personal style. “Follow your instincts about the expression of your feelings about beauty and life.” A sensational custody battle and a large trust fund left to her by her deceased father thrust her into the spotlight early on, but she channeled the drama of her youth into a passion for art and a keen eye for all things fashionable.

Diana Vreeland

She infused the pillows in her home with perfume using hypodermic needles, she ironed her dollar bills, and she adored red — but only “the color of a child’s cap in any Renaissance portrait.” Former Harper’s Bazaar and Vogue editor, and outrageous style icon Diana Vreeland lived her looks in big, boisterous ways. Her blush alone proved it. “You gotta have style,” she once said. “It helps you get up in the morning. It’s a way of life… And I’m not talking about a lot of clothes.” Need more proof of her impeccable taste? She discovered Lauren Bacall in the 1940s, she convinced Manolo Blahnik to design shoes, and she helped make Twiggy a house name. That’s just the tip of the iceberg when it comes to the woman who believed a “good hairline” was essential (she used lacquer in her own hair) and whose ideal outfit involved “luxurious cashmere; the most luxurious satin pants, very beautiful stockings, very beautiful shoes — marvelous — & whatever would be suitable around the neck.”

Karl Lagerfeld

You can’t ignore German designer Karl Lagerfeld simply because he has his own label and has been creative director for esteemed fashion house Chanel (and currently, Fendi). The 79-year-old, shockingly white-haired gentleman seems to be fueled by leather, disdain, and eccentric jewelry. Even if the slim, dark suit and signature ponytail stay the same, Lagerfeld’s style is still evolving as he makes his foray into octogenarian territory. “I am a fashion person, and fashion is not only about clothes — it’s about all kinds of change,” he reminded us.

Yayoi Kusama

If polka dots were actual life forms, avant-garde artist and psychedelic style icon Yayoi Kusama would control them with her mind powers. The 83-year-old Japanese fashionista has recently collaborated with Marc Jacobs and Louis Vuitton, but her eye for material style began in the late 1960s when she created her own distinctive clothing line. She is the embodiment of her larger than life artwork, has a penchant for rainbow sophistication, and boasts a vivid, blunt fringe.

Debbie Harry

An eternal punk princess with platinum hair and the albums to match, Debbie Harry has modernized, matured, and toned down her style somewhat, but she’s still a blonde badass whose deconstructed aesthetic recalls her CBGB days.