Anouk (Jimmy Choo)

Ever tried sprinting in stilettos? Neither have I, but if I had to, I'd pick the Anouk from Jimmy Choo. These aren't just shoes; they're a lifestyle, a painful, gorgeous lifestyle. The 'Greatest Stiletto Heels of All Time'? Please, it’s like they strutted out of the womb wearing 5-inch heels. Fans of Anouk treat walking like it’s an Olympic sport. The obsession? Unreal. You haven’t lived until you’ve seen someone try to climb stairs in these. It’s half art, half cry for help.