Truth be told I'm a guy who loves a high, high heel. It's probably why I work in accessories now. But sometimes the women I know just want to be comfortable (shocking, I know). I tell them to channel their inner Faye Dunaway—think 1967's iconic Bonnie and Clyde and go out and get this Gap embroidered loafer. The black and white is graphic and the shape is feminine and a tad tough, just like Faye's take on Bonnie. (Gap Embroidered Loafer, $39.95.)