Jennifer Aniston’s Date Night Shoes Are It Girl-Approved

Believe it or not, but there was a time before “The Rachel.” Jennifer Aniston landed her first regular television role in 1990, four years before Friends would premiere. Though she hadn’t been Chris McMillan’d yet, she was still a fashionista. And she was still turning out looks that we love to this day.

Now that I think about it, with her laidback California vibe and early aughts style reference points, Aniston might be the blueprint for everything the cool girls are loving these days. She was a capri pant lover pre-Hailey Bieber’s birth and layered her tops long before any influencer watched Hannah Montana and got the same idea. And the beach wave renaissance?! Forget about it. Or look back at her early red carpet appearances and learn a lesson or two about the look’s origins.

Then, of course, there’s the famous flip flop. She loved the rubber shoe in the ’90s and she loves it still—as do the rest of us.

Jennifer Aniston’s Modern Flip Flops

On Wednesday, August 6, Aniston bopped around New York City wearing flip flops for what might be the millionth time in her career. This occasion was special, though—they’re an official It Girl shoe of the summer, and she’s been It for a while.

For the big night out, Aniston paired her black rubber shoes with a fun gathered midi skirt, black tank top (another longtime fave), and small crossbody Bottega Veneta bag. The night before, she’d worn a different pair with a white spaghetti-strap sundress—another breezy look made possible with the versatile shoe.

Flip Flops Are Trending This Summer

Classic rubber flip flops (and some not as classic but still fun heeled options) have been everywhere this summer. Gigi Hadid kicked off a collaboration with Havaianas back in May, and we’ve since seen the shoe on the likes of Bieber, Lori Harvey, Alex Consani… the list could go on forever.

Like Aniston, these girlies are down to wear the shoe with anything. The thong has seen them through formalwear moments and vacation dinners, workout classes and errand runs.

Unlike some current trends, the reason flip flops are soaring in popularity is easy to trace. We’re obsessed with nostalgia, and there’s no easier (or cheaper, if you go the Old Navy route) way to experience the fashions of yore than slipping on a pair of rubber sandals and hearing them slap the pavement. They’re also so comfortable and easy to style.

Take it from all the It Girls… but mostly Jen.

Shop the Style

Whether you prefer West coast or East Coast styling, dressing up or dressing down, Monica, Rachel, or Phoebe, there’s definitely a pair of flip flops out there that you’ll fall in love with. Ahead, discover a few of our current favorites.