While flip-flops might seem like the last footwear option for celebrities on the red carpet, the laid-back, summer-ready silhouette has had some memorable moments on the red carpet.
The breezy shoe style has been around for thousands of years, evolving through various iterations with materials ranging from papyrus to PVC. In 2025, flip-flops are having a full-circle fashion moment — just ask Louis Vuitton, The Row or any number of stylists tasked with making “relatable luxury” look intentional.
For celebrities, the red carpet flip-flop is a studied contradiction. It plays with the tension between casual and couture, elegance and effortlessness — something stars like Kendall Jenner, Halle Berry and Jennifer Aniston have all leaned into at one point or another. And while the Y2K-era platform flip-flop may still loom large in our collective memory, today’s red carpet versions range from the barely-there to the custom and crystal-encrusted.
Whether it’s about comfort, confidence or just committing to the bit, celebrities in flip-flops never fail to spark debate, and sometimes, even set trends. Some looks were divisive, others quietly ahead of their time. Either way, they all earned a place in fashion’s favorite recurring genre: the unexpected shoe moment.
Ahead, take a look at some of the most surprising celebrity flip-flop red carpet appearances.
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Jonathan Bailey (2025)
Image Credit: Alan Chapman/Dave Benett/WireImage Mahershala Ali, Scarlett Johansson, Jonathan Bailey — who is wearing The Row’s $690 flip-flops — and Rupert Friend attend the “Jurassic World Rebirth” London Photocall at Corinthia Hotel London on June 16, 2025 in London.
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Jonathan Bailey (2025)
Image Credit: Gareth Cattermole/Getty Images Jonathan Bailey attends the “Jurassic World Rebirth” photocall at The Corinthia Hotel on June 16, 2025 in London wearing flip-flops from The Row, priced at $690.
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Kendall Jenner (2023)
Image Credit: Getty Images for Atlantis The Ro Kendall Jenner attends the Grand Reveal Weekend for Atlantis The Royal, Dubai’s new ultra-luxury hotel on January 21, 2023 in Dubai, United Arab Emirates, wearing a brown column dress from Schiaparelli by Daniel Roseberry’s spring 2023 ready-to-wear collection and The Row flip-flops.
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Kendall Jenner (2023)
Image Credit: Getty Images for Atlantis The Ro A closer look at Kendall Jenner’s flip-flops she wore while attending the Grand Reveal Weekend for Atlantis The Royal, Dubai’s new ultra-luxury hotel on January 21, 2023 in Dubai, United Arab Emirates, wearing The Row flip-flops.
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Jennifer Lawrence (2023)
Image Credit: Corbis via Getty Images Jennifer Lawrence attends the “Anatomie D’une Chute (Anatomy Of A Fall)” red carpet during the 76th annual Cannes film festival at Palais des Festivals on May 21, 2023 in Cannes, France, wearing flip-flops, which caused quite a stir.
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Jennifer Lawrence (2023)
Image Credit: Corbis via Getty Images A closer look at Jennifer Lawrence’s flip-flops at Cannes 2023.
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Janelle James (2023)
Image Credit: Getty Images “Abbott Elementary” star Janelle James attends the 28th Annual Critics Choice Awards at Fairmont Century Plaza on January 15, 2023 in Los Angeles, wearing flip-flops.
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Janelle James (2023)
Image Credit: Frazer Harrison/Getty Images A closer look at Janelle James’ flip-flops on the red carpet.
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Kendall Jenner (2022)
Image Credit: Kevin Mazur/WireImage Kendall Jenner attends the CFDA Fashion Awards at Casa Cipriani on November 7, 2022 in New York City wearing a minimalist white dress by Khaite, which won the CFDA’s Women’s Wear Designer of the Year award, and white flip-flops.
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Kendall Jenner (2022)
Image Credit: Kevin Mazur/WireImage A closer look at Kendall Jenner’s white flip-flops at the 2022 CFDA red carpet.
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Lisa Rinna (2012)
Image Credit: Jonathan Leibson/WireImage Lisa Rinna attends the 3rd Annual My Brother Charlie Family Fun Festival – Arrivals at Culver Studios on August 12, 2012 in Culver City, California wearing a strapless dress and peace sign flip-flops.
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Lisa Rinna (2012)
Image Credit: Jonathan Leibson/WireImage A closer look at Lisa Rinna’s peace sign flip-flops.
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Halle Berry (2009)
Image Credit: Lester Cohen/WireImage Actress Halle Berry arrives on the red carpet of “The Soloist” premiere wearing a striped dress and flip-flops at the Paramount Theatre on April 20, 2009 in Hollywood, California.
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Halle Berry (2009)
Image Credit: Lester Cohen/WireImage A closer look at Halle Berry’s flip-flops on the red carpet.
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Charlize Theron (2008)
Image Credit: Lester Cohen/WireImage Actor Stuart Townsend and actress Charlize Theron arrive at the World Premiere of Columbia Pictures “Hancock” at Grauman’s Chinese Theatre on July 30, 2008 in Hollywood, California. Theron opted for a strapless dress and embellished flip-flops for the red carpet.
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Charlize Theron (2008)
Image Credit: Lester Cohen/WireImage A closer look at Charlize Theron’s embellished flip-flops.
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Jennifer Aniston (2003)
Image Credit: WireImage Jennifer Aniston & Brad Pitt at the Independent Spirit Awards in Santa Monica, California, on March 23, 2023. Both opted for casual looks, including Aniston’s choice of flip-flops.
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Jennifer Aniston (2003)
Image Credit: Jeffrey Mayer/WireImage A closer look at Jennifer Aniston’s flip-flops at the 2003 Independent Spirit Awards.
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Nicole Richie (2003)
Image Credit: Jean-Paul Aussenard/WireImage Nicole Richie attending the STUFF Magazine and Blender Host Kid Rock’s After Party For The 2003 American Music Awards wearing a casual look tied together with flip-flops.
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Nicole Richie (2003)
Image Credit: Jean-Paul Aussenard/WireImage A more detailed look at Nicole Richie’s flip-flops on the red carpet for the STUFF Magazine and Blender Host Kid Rock’s After Party For The 2003 American Music Awards.
