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.
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.
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:
This comes in UK sizes 4—30.
These also come in brown, red and a snake-print design.
These also come in a deeper shade of blue.
I really can't see these staying in stock for long.
Shop these while they're on sale.
Reformation's Jessie Thongs are a fashion person's favourites.
Style with a white tee for a simple and chic summer look.
Every great summer wardrobe starts with a pair of flip-flops.
Style with flip-flops or dress these up with a kitten heel.
The platform design adds a little extra height without sacrificing any comfort.
-
Fashion People Just Gave Me 15 Fresh Ways to Wear Jeans Next MonthSave and style on repeat this fall.
-
The Denim Trends Celebrities Are Ditching, and What They're Wearing Instead for 2025Talk about a glow-up!
-
In London and Lisbon, Fashion People Are Stirring the Pot by Wearing These Anti-Fall ShoesIt's a controversial choice.
-
Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 ChicReplica Store Outfits I Put Together for Her Under $425Outdated prints and "ugly" shoes included.
-
No, Really—This Denim Color Is Easier to Style Than Blue *and* Black JeansAnd everyone with taste is wearing it with loafers for fall.
-
From Sweden to London: The Surprising Jeans Color European Fashion People Are Reaching for This FallHere's how to pull it off.
