Aged 35 or 56—Jennifer Aniston's Timeless Jeans-and-Sandals Pairing Always Works

Jennifer Aniston appreciates that some outfit combinations will never go out of style, and that jeans and flip-flops are absolutely one of them.

Jennifer Aniston wears baggy jeans and flip-flops in 20024 and 2025.
(Image credit: Getty, Backgrid)

I'll admit it—the trend cycle moves fast. But I’ll stand by this: not every trend that comes "in" is destined to be dragged "out" again. Case in point? The enduring jeans-and-sandals pairing Jennifer Aniston has been wearing since 2004.

Transcending fleeting fashion moments, Aniston has long understood the lasting appeal of a flip-flop-and-jeans combo. Styling the effortless look just this week, she stepped out in baggy mid-wash jeans, a sleeveless checked top, an elegant tan hat and, of course, a relaxed pair of flip-flops.

Jennifer Aniston opens a car door wearing a plaid sleeveless top, baggy blue jeans and brown flip-flops sandals.

(Image credit: Backgrid)

This certainly isn’t the first time we’ve seen her lean into the throw-on formula. In fact, the moment I spotted the new image this morning, I couldn’t help but recall a strikingly similar look from November 2004. Same relaxed blue jeans, same easy thong sandals—proof that some outfits really do stand the test of time.

Jennifer Aniston wears baggy jeans with black flip-flops and a black long sleeve top in 2004.

(Image credit: Getty Images)

The enduring appeal of this classic combination lies in its simplicity: denim—a wardrobe hero that, although styles and cuts may ebb and flow in popularity, will never leave our repertoire—meets the effortless appeal of a slip-on flip-flop. The gold-star standard in easy-going, chic styling, this tried-and-true combination will continue to deliver year after year.

Read on to shop my edit of the best jeans and flip-flops below.

SHOP BAGGY JEANS AND FLIP-FLOPS:

Natalie Munro
News Writer

Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.

With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.