“I dress like a boy because I feel like boys are generally more comfortable than women,” said Ali Tenenbaum the other day, sitting at a West Village coffee shop and wearing a “typical” outfit of black Hudson jeans, blue J. Crew cardigan, yellow T-shirt and designer sneakers. Ms. Tenenbaum, 38 (whose family was the inspiration for the Wes Anderson film The Royal Tenenbaums, though she said the actual resemblance is slight), has unfussy brown hair that falls to several inches above her shoulders, and clear, radiant skin. She doesn’t wear makeup. She is a professional photo organizer who meets with...