Photo: Lorenzo Agius

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The Fantasy: Timeless Elegance
Hillevi Loven, 42

Hillevi's work as a filmmaker and photographer has always dictated her style—mostly loose-fitting tops and comfortable shoes that she characterizes as "rough and ready." But now that her first feature documentary, Radical Love, is being released later this year, she's eager for a more sophisticated look. "Long, unstyled blonde hair worked well in the backwoods of North Carolina, where I've been filming for the past several years, but I've always wanted to look more feminine and put-together," she says.

Top, $960, and skirt, $10,500, Dior; 800-929-3467. Necklace, Anton Heunis, $750; Shoes, Roger Vivier, $725; 212-861-5371.