Kate Bosworth wore two memorable Jimmy Choo sandals during Hollywood’s 2020 awards season, pairing crystal-embellished Jimmy Choo Thyra sandals with Ralph Russo couture at the Vanity Fair Oscar Party and minimalist Jimmy Choo Kaylee sandals with a vibrant Prabal Gurung gown at the InStyle and Warner Bros. Golden Globe after-party.
Both appearances took place in Beverly Hills in early 2020 and showcase two distinct approaches to modern red-carpet dressing built around elegant evening shoes.
Kate Bosworth Sparkles in Jimmy Choo Thyra Sandals With Ralph Russo Couture at the 2020 Vanity Fair Oscar Party
Kate Bosworth attends the 2020 Vanity Fair Oscar Party with Michael Polish in a shimmering Ralph Russo Spring 2019 Couture gown, styled with Jimmy Choo Thyra crystal sandals, a Jimmy Choo Leonis clutch, and a dramatic black velvet train on February 9, 2020, in Beverly Hills, California (Credit: Instar / WENN)
At the Vanity Fair Oscar Party on February 9, 2020, at the Wallis Annenberg Center for the Performing Arts in Beverly Hills, Bosworth paired her intricately embellished Ralph Russo Spring 2019 Couture gown with Jimmy Choo’s crystal-embellished Thyra sandals, a red-carpet favorite also worn by stars including Olivia Wilde and Nicole Kidman.
Set on a 100mm (approximately 4-inch) stiletto heel, the elegant sandals feature an open-toe silhouette, a pavé crystal knot across the vamp, crystal-encrusted ankle straps, and a delicate side buckle fastening.
Bosworth completed the look with a Beladora diamond bracelet woven into her hairstyle and a Jimmy Choo Leonis clutch. Originally retailing for $1,495–$1,795, the seasonal Thyra sandals have long since sold out at retailers, though well-preserved pairs still appear on luxury resale platforms for collectors seeking one of Jimmy Choo’s standout evening designs of the era.
Kate Bosworth showcases the intricate embellishment of her Ralph Russo Spring 2019 Couture gown, accessorized with a Jimmy Choo Leonis clutch, Beladora diamond jewelry, and a sculptural black velvet shoulder bow
Kate Bosworth Pairs Jimmy Choo Kaylee Sandals With a Pink Prabal Gurung Gown at the 2020 Golden Globe After-Party
One month earlier, at the Golden Globe after-party at the Beverly Hilton Hotel, she contrasted a bold pink Prabal Gurung Pre-Fall 2020 gown with understated Jimmy Choo Kaylee sandals, allowing the clean-lined heels to balance the dramatic open-back silhouette.
Kate Bosworth wore a vibrant pink Prabal Gurung Pre-Fall 2020 gown styled with Jimmy Choo Kaylee sandals, while Sophia Bush paired a light blue John Paul Ataker gown with Jimmy Choo accessories and Anita Ko jewelry
She completed the look with David Webb rings, Prabal Gurung x Tasaki “Waterfall” earrings in white and rose gold set with diamonds and Akoya pearls, a gold Bienen Davis clutch, and Jimmy Choo’s Kaylee sandals.
Defined by delicate crisscross straps, an open toe, and an elegant ankle-wrap fastening, the minimalist 100mm stiletto became a red-carpet favorite for its leg-lengthening silhouette, appearing on celebrities including Gwyneth Paltrow at the “Avengers: Infinity War” premiere before Bosworth styled the design with her vibrant Prabal Gurung gown.
Although the Kaylee has long since disappeared from Jimmy Choo’s retail lineup, its minimalist silhouette continues to influence the brand’s evening footwear.
As of July 2026, Farfetch’s Jimmy Choo selection highlights contemporary styles such as the Azia, Jenn, Rafi, Coko, and Moza sandals in place of the retired Kaylee. Original pairs now surface primarily through luxury resale platforms, where the elegant strappy design remains a sought-after red-carpet classic.
Kate Bosworth styled her Prabal Gurung dress with Jimmy Choo shoes, Tasaki earrings, and David Webb jewelry at the 2020 InStyle and Warner Bros. 77th Annual Golden Globe Awards Post-Party at The Beverly Hilton Hotel in Beverly Hills, California, on January 5, 2020
Explore More of Kate Bosworth’s Signature Designer Shoe Moments
Whether she’s wearing crystal-embellished Jimmy Choo sandals on the red carpet or sleek over-the-knee boots for a fashion event, Kate Bosworth consistently pairs refined tailoring with standout footwear. Discover more of her most memorable designer shoe moments below.
- 📏 Standing at 5’5″ (165.1 cm) and wearing a US shoe size 8, Kate Bosworth regularly uses sleek stilettos, ankle-strap sandals, and sculptural heels to sharpen her polished red-carpet looks.
- 💎 See how Jimmy Choo’s crystal-knotted Thyra became an awards-season favorite, with Bosworth joining Scarlett Johansson, Gabrielle Union, and Olivia Wilde in styling the pavé-embellished evening sandal.
- ✨ Revisit the Jimmy Choo Kaylee sandals at the 2018 Met Gala, where Rosie Huntington-Whiteley paired the delicate gold straps with a crystal-covered Ralph Lauren cape gown alongside Bosworth’s gilded Oscar de la Renta look.
- 🌟 Take a closer look at the Thyra’s crystal-encrusted straps and open-toe silhouette, revisited on Kerry Washington with a nod to Bosworth’s shimmering Ralph Russo pairing at the 2020 Vanity Fair Oscar Party.