13. Kurt Angle
Kurt Angle's early years in the WWE painted him as the very opposite of cool. He was a dorky, good-natured jerk, entirely at odds with the Attitude Era due to his wholesome outlook and boy-next-door appearance. In other words, he was the perfect heel. However, looking back, Angle looked damn cool. His amateur wrestling singlet has become a career trademark, and always helps emphasise his untouchable in-ring work. As the years progressed and Kurt began to unleash a more ruthless streak, the vibrant reds and blues were eventually darkened (and occasionally became entirely black), but the old school effect always remained. An added bonus provided of the singlet is Kurt's tendency to pull down the straps as a match nears its conclusion - a clear sign that things are about to kick into high gear.