Fashion Eccentrics
Iris Apfel celebrating her 100th birthday in style. Courtesy of Noam Galai/Getty Images for Central Park Tower

The fashion world lost a legend in March this year. Iris Apfel, who lived until the grand old age of 102, was a rare breed of fashion eccentric whose colorful legacy, iconic signature style, incredible story and life, not only hit a chord, it enchanted the entire world. Fashion mavericks like the legendary Apfel stand out because pushing style boundaries is like breathing to them — entirely natural — they don't even try. With her close crop of white hair, the black glasses that enlarged her eyes and her penchant for feathers, she was the consummate fashion bird, a peacock who made maximalism a way of life. One of her oft-quoted bon mots is "Great personal style is an extreme curiosity about yourself." It's a sentiment that resonates in a time when the conversation turns so often to authenticity. Luckily, there are several fellow unconventional fashion luminaries to take on the mantle.

It's not every day an octogenarian gets a retrospective of her closet at The Metropolitan Museum of Art. But that's exactly what Apfel received in 2004, the first non-designer to be featured. Apfel wasn't your everyday octogenarian or human for that matter. A force of nature, a bohemian in the truest sense, an interior designer with a loving husband (how her documentary Iris hit an emotional chord cannot be overstated), a lover of bangle bracelets, a keeper of a hit signature piece — those oversized black framed glasses — a New Yorker, an ace shopper and a born-and-bred fashion lover (her mother owned a boutique in Queens). For someone to hit the zeitgeist as deeply as Apfel did is because she was sharing her truth with the world — and her medium was style.

Can you be an authentic minimalist? Of course. But there's something that feels particularly living out loud about a bold, eccentric style maven. And there are people carrying the Apfel torch unwittingly or not. Cleo Davis-Urman, industry vet, founder of Barrière and author of Fashionably Late, is a New Yorker who regularly saw Apfel out and about and, as they say, game recognizes game. "She is a fashion icon, but unlike many in the pantheon, she dressed herself with joy and embraced the idea of surprise," she explains. "Our only expectation was that whatever Iris wore would be quintessentially Iris — that's true style."

Davis-Urman, not unlike Apfel, has a fondness for integrating vintage into her looks and has fun with color. "These days, I feel that the conversation around personal style is a little prescriptive and rigid and promotes the idea your style (with a carefully curated wardrobe) is one look that defines you and any deviation is inauthentic," she explains. "I'm a little more spontaneous and never want to be defined by one word in a dictionary. My approach to dressing is a more emotionally driven exercise. I dress for how I feel — or want to feel — in a particular moment."

Leandra Medine's outfits have been chronicled in the media and on her own various platforms since she was in her early 20s — an entirely 21st century phenomenon. It's because Medine's style is so entirely watchable. That fun-with-fashion mentality is contagious, after all, and it comes from a true place of enthusiasm.

"I love getting dressed and love beautiful clothes but always want to strike a balance between the clothes I'm wearing and conveying a sort of rough edge that makes it feel more real," the author of The Cereal Aisle explains. "I think that's most important to me — that I look real, as in an accurate and practical reflection of myself, when I'm dressed."

Medine is also known to take risks, playing with color, proportion and accessories in every look she wears. "I usually either play up bold pieces with other bold pieces that conflict (when I can create harmony between the conflict) or use the bold piece as the centerpiece item and build softly around it," she says. The results are almost always not what you're accustomed to seeing — a sure sign of a true eccentric.

Jalil Johnson came into the New York style world from Hurt, Virginia like an old-school fashion fairy tale — he is the fashion office coordinator at Saks, author of the Consider Yourself Cultured newsletter and the latest fashion week street style mainstay. Somehow, a Capote Swan-worthy gown, a pencil skirt and field jacket and a sailor sweater prep moment all feel on-brand for Johnson. How does he play in so many different style arenas and keep it real? "If I were to offer one key piece of advice, it would be to embrace experimentation. True self-discovery in style and, by extension, finding comfort within ourselves, often stems from exploring various styles," he explains. "Moreover, it's essential to acknowledge that making mistakes is inevitable and an integral part of the journey toward self-assurance."

For Johnson, style is part of his birthright. "Growing up amidst influential women [like his mother and grandmother] and attending church where style was akin to holiness, sparked within me an unquenchable thirst for sartorial expression," he says. "I've always felt compelled to dress in a way that reflects my true self. I am incredibly humbled to receive admiration for my style; every time someone approaches me about loving how I dress, I have to pinch myself — it feels surreal. While this praise has encouraged me to push the boundaries of my style even fashion choices remain a reflection of my own satisfaction and self-expression."

So much of making offbeat style work is the effortlessness with which you wear it. Confidence is not something that can be taught, it's innate, perhaps earned. But there are methods to embody it. "I think the thing about personal style is that it's exactly the overlap on the Venn diagram between your taste and your understanding of your body — what suits you, what doesn't, what body parts you love and which you're less inclined to accentuate and that coming to terms with it and even celebrating it is what makes you comfortable in your skin," Medine says. "It's the difference between feeling overwhelmed by clothes and empowered by them." It's also getting dressed according to the age-old sentiment of wearing the clothes and not letting them wear you.

If there's a living example of having fun with fashion now, dressing boldly and joyfully, it's fashion retail professional Chloe King. If there's one throughline of King's style, it's a sense of adventure and a knack for layering — an inclination she shares with Apfel. "I was always particularly attracted to the way Iris piled on jewelry — interesting combinations of colors and textures, bountiful layers around her wrists and neck," she says. "I was fortunate enough to meet her on a few occasions and she was equally unpretentious about how she acquired her treasures: pieces mixed from her extensive travels, family heirlooms and thrifted finds. Combined, the look was completely her own."

Being eclectic in your style is just that — always surprising, never formulaic. "I don't feel particularly committed to a certain style, instead favoring a more adventurous sartorial spirit," King continues. "I think I'm certainly a fashion enthusiast. And through that curiosity I am happy to take risks and try new things. Remaining open-minded is essential to evolving creatively — I get just as excited about a weird little hat I find in a thrift shop as I do about a new season pair of designer shoes. For me the beauty, even if unorthodox, is not each individual piece but how it comes together."

In a sea of quiet luxury, staid minimalists and people for whom wearing all black is a way of life, the fashion eccentric will always emerge like a balm for the eyes and maybe the soul. Apfel's legacy lives on in every style risk-taker, whether they gravitated toward the fashion industry, like those mentioned here, as well as Gabriella Karefa-Johnson, Julia Sarr-Jamois, Anna Piaggi and Grece Ghanem; or live and work in other arenas, like Buffalo Bills wide receiver Stefon Diggs or Los Angeles Clippers Russell Westbrook; or Harry Styles and Rina Sawayama in the music realm. Dressing boldly is ageless, timeless and has nothing to do with gender or body type.

When done well it's pure expression. "Dressing isn't merely functional; it's a powerful, sometimes rebellious gesture," Johnson says. "And at its core, it should always be rooted in joy."

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