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.
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Cindy Crawford Has Been Wearing This '90s-Supermodel Jean Outfit For 25 Years—and It's Still Just as ElegantVery model-off-duty.
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This Denim Wash Will Have You Looking Like a Fashion Person This WinterThese jeans make any outfit look more expensive.
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It's Official: The Best Shoe Color to Wear With Blue Jeans Was Considered "Dated" a Year AgoChocolate brown has some competition.
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When L.A. Girls Wear Leggings or Sweatpants, They Pair Them With Jennifer Lawrence's $35 SlidesAffordable and so versatile.
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Jennifer Aniston Just Wore the Sneaker Color That Makes This Dated Denim Trend Look 2025A '90s-inspired outfit formula.
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Jennifer Aniston's 1999 Airport Outfit Formula Is Still Worn by the Chicest Passengers at LAX, CPH, and CDGHere's how to copy it.
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Scarf Belts Won't Look Dated *If* You Wear Them With This Skinny-ish Denim TrendProof is inside.
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These Designer Jeans Make Me Feel Like a Grown-Up With Excellent Credit and Even Better TasteI'm just another fashion insider who's obsessed with them.
