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7 Champions Of Quirky Style Who Will Inspire You To Have Fun With Dressing

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In Diana Vreeland: The Eye Has to Travel, it quotes the legendary Vogue EIC making a keen observation about fashion taste. "Style — all who have it share one thing: originality." Though it's been 30 years since her passing, the sentiment couldn't feel more relevant. The industry's abundance of newness — new clothing arrivals, new Instagram outfits, new fashion brands — is not necessarily the answer to achieving the sort of quirky style definition Vreeland was hinting at. The women who best embody originality are often reimagining what they already own, rather than relying on fresh items to hit the shelves.

"I always feel most 'me' when something is a little off, so that usually means I don’t go with the most intuitive way to wear something," Chloe King tells TZR. She's the Fashion Office and Digital Lead at Bergdorf Goodman and is known on the street style circuit for embracing colors, prints, and silhouettes in an unusual way. "A masculine coat with a super femme corset, a sequin dress with a Yankees cap, a modern trouser with a beaded vintage cape," she says, listing off a few favorite outfits. "I live with my boyfriend and generally if he doesn’t 'get it', it’s good."

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For inspiration, King looks to other boundary-pushing dressers of the moment. "The way Ana Gimeno Brugada mixes prints, color, and menswear pieces. Or Michelle Elie, completely at home in every amazing Comme des Garçons piece she wears. Walking art. That authenticity and adventurous spirit are so energizing. I don’t get awestruck like that about a clean, simple slip dress."

King observes this predilection for the slightly off-kilter is likely something you're born with. "I really believe people are naturally pulled one way or the other, and I’ve always liked a big personality ... in art, music, and clothing," she says. "It’s a more joyful expression to me. I get a better sense of who you are and how you think. I have two sisters and growing up I was the first to ditch the matching outfits. Ever since then, personal expression has been important to me."

Ahead, refresh your memory on women — both designers and dressers — who are championing a quirky, original aesthetic. Follow each for inspiration for your own unique wardrobe.

Iris Apfel

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The 98-year-old icon captured hearts in the 2014 Albert Maysles documentary that spotlighted her bold personality and even bolder sense of style. "Life is gray and dull, you might as well have a little fun when you dress," she famously quipped. Embrace her look with a pair of oversized round frame glasses, or simply try oversized jewelry on for size.

Gabriella Karefa-Johnson

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Garage Magazine's Fashion Director Gabriella Karefa-Johnson has blossomed on the street style circuit in part thanks to her exuberant outfits. She has the kind of look that's delightfully unpredictable and she can mix and match prints and colors like a pro.

Collina Strada

Collina Strada

New York-based designer Hillary Taymour and her label Collina Strada are part of a new wave of fashion brands that are eschewing the traditional trend cycle. Her fashion week events have included a sound bath, farmer's market, and environmentalist speeches. Her sometimes post-apocalyptic clothing offers an entirely unique aesthetic, season after season.

Lynn Yaeger

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New Yorker Lynn Yaeger is a journalist whose work spans several decades, including thirty years at The Village Voice and regular contributions for Vogue and WSJ. Her style is unmissable — vibrant red hair, doll-like makeup, and a voluminous assortment of dresses, layers, and prints.

PRISCAVera

PRISCAVERA

Add PRISCAVera to your list of brands to go to for unusual, interesting pieces. The New York-based label feels fresh with each collection but always embodying quirky sensibilities.

Diana Vreeland

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Diana Vreeland needs little introduction. The legendary editor celebrated individualism and has inspired generations of women to not "be boring" when it comes to getting dressed.

Chioma Nnadi

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Vogue's Fashion News Director Chioma Nnadi reliably serves up a healthy portion of enticing pieces styled together in head-turning ways. Originally from London, her unique approach to pairing layers together makes her outfits feel akin to paintings on a canvas.