The more things change, the more things stay the same. Jennifer Lopez has worn the same boot trend for 18 years while Kate Middleton keeps bringing back her beloved shoes year after year. Meanwhile, Jennifer Aniston has stayed partial to trusty flip-flops. In fact, she’s been wearing them consistently from 1999 all the way to today. While the shoes are sometimes controversial—are they appropriate for non-beach days or not?—you simply can’t blame her for relying on the ultimate no-fuss, slip-on-and-go shoes. Plus, plenty of other celebs are also fans, including Mary-Kate and Ashley Olsen.
Over the years, Aniston has worn the shoes on casual shopping trips and even on the red carpet. In 2003, she attended the Independent Spirit Awards red carpet wearing a laid-back outfit that certainly lived up to the name of the awards show: a simple black tank top, skirt, and her trusty flip-flops. (Oh, and her then-husband Brad Pitt on her arm as well.) Scroll down to see seven different ways Jennifer Aniston has worn flip-flops over the last 20 years and shop 2019 versions of her iconic looks.