Jennifer Aniston Styles Her 'Friends'-Era Flip-Flops With a $3,000 Bottega Veneta Bag

Jennifer Aniston was a flip-flop fan long before Kendall Jenner and Hailey Bieber declared them summer 2025's It shoe. Aniston started styling them in her Friends days and she hasn't stopped. On August 6, the L.A. actor looked every bit a native New Yorker in her signature shoe, plus a four-figure Bottega Veneta bag.

Though Aniston lives in a Bel-Air mansion, she arrived at her Manhattan hotel on Monday with her black flip-flops on display. These former New York no-no's have landed in the closets of locals like Zoë Kravitz and Jennifer Lawrence, so Aniston looked right at home. If they're anything like her other versions, they're from Tkees.

While Jennifer Lopez can't stop wearing their $60 Lily model in metallic gold, Aniston paired hers with a high-neck tank top and a midi skirt, both in black. Her purse of the day was a relatively new purchase from Bottega Veneta: the Cassette Medium Leather Bag. She chose the $3,000 taupe colorway, which she debuted in late June. A month later, it joined Aniston on vacation in Mallorca.

Both on- and off-screen in the '90s, Aniston always had flip-flops at the ready. In 1998, she attended a charity event in a platform taupe pair, which stayed in her regular rotation for years to come. Aniston's sandal-clad outfit, from the micro-jorts to an oversize leather tote, still influences fashion enthusiasts today.

In March 2003, Aniston's flip-flops made it to a red carpet event. The Rumor Has It star attended the Independent Spirit Awards in a slingback style, alongside another black skirt set. Between the tank top and the knee-length midi, there's a chance it inspired Aniston's latest look.

It's typical for New Yorkers to change outfits before stepping out again in the same day (see J.Law). Aniston, however, re-wore her combo at San Vicente Bungalows once the sun set, down to her flip-flops. You heard it here: They're daytime- and nighttime-tested.

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