Robbie

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“I’m eclectic—unique,” the Alexander Wang account executive grins, discussing her personal style but also, one gathers, her story.

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 Indeed, Stuart’s grandmother is called Pepper “because she definitely has bite. She doesn’t mess around.” Pepper met her husband, Stuart’s grandfather, while deciphering morse code from Japanese troops during the Second World War. “She never read fashion magazines. She’s not girly-girly,” Stuart allows. “When I told her I was interested in fashion, she was like, ‘What?’” What Pepper has, however, is a singular style comprised mainly of oversized menswear staples such as the tweed blazer Stuart is wearing today.

robbie-jeremy-allen3 Photo: Jeremy Allen

Leslie

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Leslie Kirchhoff remains a modest Midwesterner at heart despite her status as a quintessential SoHo cool girl. Photo shoots for Vogue, Teen Vogue, Glamour, GQ, Elle, Marie Claire, Refinery29, among others. High profile DJ gigs at the Standard and TriBeCa Grand. And yet, Kirchhoff’s favorite keepsake is a fire-engine red Wisconsin University marching band jacket from her father.

leslie-jeremy-allen-3 leslie-jeremy-allen-4 leslie-jeremy-allen-6 leslie-jeremy-allen-7 leslie-jeremy-allen-8Photo: Jeremy Allen

Liana

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New York City has long been celebrated as a melting pot of rich cultures, and it is with people like Liana Weston who keep the mix fresh. Drawing upon her Mexican grandmother’s artistic flair and worldly style, Liana shakes up the sartorial scene at Into The Gloss’s Glossier, where she is the Talent and Bookings Manager. Liana’s grandmother, fondly called Tika, would undoubtedly have been proud of her granddaughter, as she herself was an ardent follower of fashion—much influenced by her travels and the people she met along the way. “My grandmother’s style was always refined,” Liana reminisces fondly, and yet the way in which Liana incorporates Tika’s heirlooms into her own wardrobe always telegraphs 21th century cool.

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Molly

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“I always knew I wanted to do something creative,” globe-trotting stylist Molly Kennedy explains. “I just fell into styling and I loved it. But I’ve always been open to a lot of careers. I never had just one in mind.” Kennedy, who studied art history, has had prominent gigs at Vogue and Victoria’s Secret PINK, among others, pulling inspiration from her childhood home steeped in a reverence for the past (her father is the head of the Historian Association in Nantucket). “I’m a romantic. I love old things. I think it was my dad’s influence,” Molly muses. But with her new opportunities at Jetworthy.com and dELiA*s, Molly’s eye is definitely attuned to the future. That penchant for nostalgia is just the jumping-off point.

molly-jeremy-allen11 “This locket was my great grandfather, Robert Joseph Kennedy’s. I have a beautiful trunk with his name on it that he had when he came to America.”molly-jeremy-allen3 molly-jeremy-allen4 molly-jeremy-allen5molly-jeremy-allen10 molly-jeremy-allen6 molly-jeremy-allen7 molly-jeremy-allen9Photo: Jeremy Allen

Katherine

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Katherine Bernard is the last person to term herself a tastemaker, but the tag can’t help but stick. The freelance fashion writer—whose clients include Vogue, the Wall Street Journal, Dazed and Confused, and The Paris Review Daily—files from her bright Bushwick loft when not bounding from one boîte to another in Paris or Milan. This is all, of course, when she’s not heading up her own literary website, Henry.

katherine-jeremy-allen-2 katherine-jeremy-allen-3 katherine-jeremy-allen-4 katherine-jeremy-allen-5  Figuratively, it’s a long way from where her great grandmother, Anna Fuchs, grew up, even though it was just a stone’s throw across the East River on the Lower East Side. Long before hipsters thronged Hester Street, one can imagine that Fuchs and her nine siblings dreamed of a life beyond their cramped tenement.katherine-jeremy-allen-6“She went from fairly modest beginnings to a very cool and exciting life,” Bernard explains, flicking to a photo on her iPhone of her great-grandmother standing with her husband in front of their house in Mt Vernon, draped in a fur coat circa 1930, her hair set with Joan Crawford-esque precision. Style savvy inherited, no doubt.katherine-jeremy-allen

Photo: Jeremy Allen