The actress has come a long way since “The Rachel” (which she has since called “the ugliest haircut I’ve ever seen”), but Jen is still one of the biggest tress-setters in Hollywood. She’s mastered wavy layers, super-sleek strands and sexy ponytails—and now she’s adding the blunt bob to the list. It’s her second time sporting the style—and she obviously doesn’t have any first-time jitters!