Notable partners: Kate Moss, Winona Ryder, Amber Heard
In the '90s and early '00s, Johnny Depp rocked a grunge and bohemian look, which wasn't half bad. But today, his style is a lot more "ecclectic", though that's just a nicer way of saying his outfits are pretty crazy. The actor dresses like Jack Sparrow's hippie, cowboy counterpart who really, really likes pinstripes. But crazy or "ecclectic", Depp's wooed some of Hollywood's hottest women (some named above), and has even been rumored to have dated Naomi Campbell, Angelina Jolie, and Penélope Cruz. Life's not always fair.