Show + Tell: Writer and App Creator Felicity Sargent

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It’s fitting that we developed an e-crush on writer Felicity Sargent before ever meeting her as the Vermont-born New Yorker basically lives in front of her many screens, penning a column for Vogue.com and building her creative dictionary app, Definer. But there’s no way to capture her charm, easygoing elegance and eclectic style with an emoji, so we met up with Felicity IRL, as they say, to chat about her childhood on a farm, her country-meets-city style and the power of words.

Growing up on her parents’ farm in Windsor, Vermont (current population: 3,553), Felicity was immersed in the small town life of a place she describes as having “more sheep than people.” Perhaps fittingly, she even remembers delivering a lamb with her bare hands when she was a child. Though she now leads a busy urban life, as the saying goes, “you can’t take the Vermont out of the girl.” It’s still easy to imagine her in denim and a felt hat on horseback and when pressed to pick just two favorite pieces of clothing, Felicity named a Carhartt onesie and a scarf. But the city has made its way into her closet, and among the jeans, leather jackets and ankle boots are pastel-hued vintage pieces, wild patterns and sequined heels. The mix is very Parker Posey in Party Girl—a character whose bold style she admires.

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At the top, Felicity is wearing our Silk Stargaze Dress. Here, she is wearing our Rivet & Thread Collarless Workshirt, High Riser Skinny Skinny Cut-Edge Jeans, a Biltmore® & Madewell Felt Fedora and The Ames Boot.

Felicity’s love of vintage clothing comes from her mother, who has saved every piece of her clothing from the ’60s on. “I really didn’t shop at stores growing up, because the nearest mall was hours away,” she says. Now, Felicity visits the Chelsea Flea Market Garage almost every weekend. Vintage shopping can be tough for someone so petite—Felicity maybe hits 5’4” in heels—but she’s a believer in risk taking and great tailoring. “You never know where your day will take you, where you’ll go or who you’ll meet, so I always wear something I feel comfortable and confident in.” In clothing terms, that translates to boyjeans, natural fabrics like chambray and comfortably oversized silhouettes…coupled with a leopard-printed bootie here, some neon leather there, of course.

Her small town childhood also taught her to value connection (as she says, “you can’t tell a good story unless you’re an excellent listener”) and her career is now all about the written word. In her monthly “Connected” column for Vogue.com, she muses on the intersection of tech and culture, asking questions like, “are emojis making us emojinally unavailable?” She also developed Definer—a mobile app dictionary of user-submitted words like “underdresstimate” and “infactuation”—to explore how we use language. Her “linguaphile” team just moved into the New Museum’s NEW INC offices, the first museum-led incubator that supports artists and tech entrepreneurs with this collaborative place to work.

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Photography by Angi Welsch

Here, Felicity is wearing our Maison des A.R.T.S. Sweatshirt and Vans® & Madewell SK8-Hi High-Tops with our Reversible Bomber Jacket.

The rustic and rural moments of her childhood are still with her, giving her both the fearless attitude and boundless curiosity that still drive her. Case in point: She plans to spend the next few months fixing up the rundown barn in her parents’ backyard, analyzing trends in the words submitted to Definer and immersing herself in the creative environment offered by her new offices in one of New York’s most interesting downtown museums. This, we have come to realize, is a typical ball-of-energy Felicity agenda.