Jennifer Aniston: Making Flip-Flops Look Chic Since '99

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.

Jennifer Aniston's flip-flops obsession peaked in the late '90s and early 2000s, and this is one of our favorite highlights. 

How cozy does she look? Photographed at the airport, Aniston's 2003 outfit is actually very 2019. 

Flip-flops for the red carpet—why not? Aniston was the epitome of a cool California girl at the Independent Spirit Awards in 2003. 

A white tank top and denim shorts will always be cool. Just add platform flip-flops for the ultimate Aniston effect. 

A flowy black midi dress is one of the most versatile pieces out there, and we're quite partial to the Reformation version below. 

Would you dare to wear flip-flops to work? If so, this blazer-and–army pants outfit combo is an ideal place to start. 

Aniston's shoe obsession continues into 2018—can you blame her? The only thing she loves more than flip-flops, perhaps, is denim cutoffs. 

Next, Amal Clooney wore the shoes you've always avoided wearing to the airport.