Calling Annie Hall—celebrity trendsetters are trying on toppers with masculine appeal. Dina Pisani of Cha-Cha’s House of Ill Repute in New York City has designed hats worn by Lindsay Lohan and Ashlee Simpson. “Fedoras are a classic, like a great pair of sexy jeans,” she says. She recommends considering your height and hairstyle when choosing a hat. “Taller women usually need a wider brim,” she says, “As do women with curly, fuller hair.” And don’t forget to add a little menswear flair. “Fedoras should be worn at an angle,” says Pisani. “Think Greta Garbo.”

—Betony Toht