In 1989, before Chris Martin, Brad Pitt, Luke Wilson and even fame had come knocking, Gwyneth was already something spesh in the style stakes. With hoop earrings and a black crossover crop top (the late 80s killer combo doncha know), plus her side-flipped brunette mane, she had laid-back summer all sewn up. Do it today by adding mom jean shorts, skate shoes and va-va-volume to your hair.