Publication: Vogue Italia, September

Before Evangelista could utter the now-infamous quote, "We don't wake up for less than $10,000 a day," the muse was steadily working her way up to becoming up icon. Her power couldn't have been more evident than it was in 1988, when she chopped off her gorgeous looks, which had designers canceling her runway gigs but women across the world emulating her shorter hairstyle.