Brad Pitt
Credit: David McNew / Getty Images

Brad Pitt has had his share of hairstyles: a cowboy mullet in 1991's Thelma and Louise, super short in 1999's Fight Club, and those frosted bangs in 2001's The Mexican. But he always seems to return to shoulder-length locks, which have contributed to some of his most iconic looks over the past 30 years. Most recently, he wore his hair long for two years while filming 12 Years a Slave and World War Z. "He's the best example for nudging guys to experiment with their hair because he can wear his at any length and it looks awesome," says DiMauro.