My Boyfriend's Mom, the Style Icon

At 15, cutting school to do test shots at Coney Island, she already had her breezy, blithely chic look.

Candy Marks (later, fittingly, Candy Bull) started modeling in 1966—she'd leave school on Long Island at noon and ride into New York to be photographed. You can see her glamorous-tough style in this picture: It makes the mod dress and bold eyeliner that much cooler! Today, her eyes are still kohl-rimmed and smudgy, and her signature look involves Isabel Marant ankle boots, some kind of loose-fitting-yet-shapely vintage dress, a shrunken Rick Owens leather jacket... very Candy Bull. —Megan O'Neill, Lucky associate beauty editor

If you've got long hair, earrings can be hard to see—go for big!