Kate Upton’s Red-Carpet Style: Jimmy Choo Shiloh Sandals vs. Metallic Pumps

Kate Upton’s red-carpet style often comes down to proportion, and two all-black looks show how differently similar pieces can work.

At the Marriage Story screening during the Venice Film Festival in Venice, Italy, on August 29, 2019, she wore a waist-defining Twinset wrap gown with Bulgari Serpenti jewelry and crystal-trimmed Jimmy Choo Shiloh sandals.

The combination gave each element room to register: the wrap silhouette framed the jewelry, while the gown’s leg-baring cut revealed just enough of the embellished sandals.

Two years earlier, Upton had taken a very different approach to black eveningwear at Harper’s Bazaar’s 150 Most Fashionable Women celebration, pairing a tuxedo-style blouse and satin pencil skirt with metallic pointed-toe pumps. Together, the appearances offer a useful contrast in how fit, texture, and footwear can shift an outfit’s balance.

Kate Upton Pairs a Twinset Wrap Gown With Jimmy Choo Shiloh Sandals in Venice

Kate Upton in a Twinset black wrap gown and Jimmy Choo sandals at the Marriage Story screening held during the 2019 Venice Film Festival at the Sala Grande in Venice, Italy, on August 29, 2019 (Credit: Cinzia Camela / WENN)

Against the simple black gown, Upton’s Bulgari ‘Serpenti’ snake necklace became the focal point. Its sculptural gold coils followed the gown’s open neckline, while matching serpent earrings carried the motif through the rest of the look.

Kate Upton wearing a gold Bulgari Serpenti snake necklace and snake earrings (Credit: Cinzia Camela / WENN)

A side-parted hairstyle and muted red lip kept the beauty look understated, leaving the jewelry and shoes to provide the shine. Below the gown’s slit, Upton wore Jimmy Choo ‘Shiloh’ sandals, an open-toe design finished with jeweled straps across the toes and around the ankles.

The delicate straps suited the gown: instead of competing with its draped silhouette, the sandals added sparkle while leaving most of the foot exposed. Carrie Underwood has also worn the crystal-embellished Shiloh, pairing the black suede version with a dramatic Nicolas Jebran gown.

Kate Upton’s pink pedicure peeks through the crystal-embellished toe and ankle straps of her Jimmy Choo Shiloh sandals

Jimmy Choo produced the Shiloh in several finishes, changing both the upper and the crystal embellishments to give the same strappy silhouette distinctly different effects.

The style is no longer a current-season staple, but it still surfaces on the resale market. As of August 2026, Farfetch lists a pre-owned pair of Jimmy Choo Shiloh crystal-embellished sandals for $595, though price and availability can change.

Jimmy Choo Shiloh Jewel-Embellished Sandals in Black Suede, $1,295

The holographic leather version, for example, features multicolored crystal embellishments, while black suede, metallic gold, and yellow suede editions offer more tonal interpretations of the same jeweled design.

The Shiloh’s combination of barely-there straps and jewelry-like crystals also made it a recurring red-carpet choice: Heidi Klum later wore the Jimmy Choo Shiloh with couture at an Oscars event.

Shiloh Jewel-Embellished Sandals in Holographic Leather, $1,325

Shiloh Jewel-Embellished Sandals in Gold, $1,295

Shiloh Jewel-Embellished Sandals in Yellow Suede, $1,295

Kate Upton’s Metallic Pumps Add Shine to a Black Satin Look at Harper’s Bazaar

Two years earlier, Upton took a more tailored approach to black eveningwear at Harper’s Bazaar’s Celebration of the 150 Most Fashionable Women at Sunset Tower Hotel in West Hollywood.

She joined fellow models Kendall Jenner and Miranda Kerr in a sheer-sleeved tuxedo blouse, lace-trimmed satin pencil skirt, and metallic pointed-toe pumps.

Kate Upton shows how to wear a sheer-sleeved tuxedo shirt with a lace-hemmed black satin pencil skirt (Credit: Adriana M. Barraza / WENN)

The individual pieces had evening appeal, but their proportions didn’t work together.

Tucking the voluminous tuxedo blouse into a close-fitting satin skirt created visible bunching beneath the thin fabric, interrupting the otherwise streamlined pencil silhouette.

Kate Upton wears a sheer-sleeved tuxedo shirt sloppily unbuttoned at the collar (Credit: Adriana M. Barraza / WENN)

The contrast is especially noticeable beside her Venice wrap gown: rather than a body-type issue, the difference comes largely from construction and layering. The wrap dress defined the waist without adding bulk underneath another fitted piece.

The metallic pumps brought a sharper finish to the outfit. Their pointed toes visually extended the line of the pencil skirt, while the iridescent gold finish broke up the otherwise all-black palette.

Kate Upton at the Harper’s Bazaar celebration of the 150 Most Fashionable Women presented by TUMI in partnership with American Express, La Perla, and Hearts On Fire at Sunset Tower Hotel in West Hollywood, California, on January 27, 2017 (Credit: Adriana M. Barraza / WENN)

The pumps were not definitively identified, but their pointed toe, slim stiletto heel, and metallic finish resemble the Stuart Weitzman “Heist” pump.

It’s a different proposition from the barely-there sandals frequently seen on the red carpet — including Emily Ratajkowski’s Stuart Weitzman Nudist sandals — with the closed, pointed toe creating a longer, sharper line beneath Upton’s pencil skirt.

Kate Upton shows off her feet in pointy-toe pumps with an iridescent gold sheen (Credit: Adriana M. Barraza / WENN)

More Kate Upton Shoe and Red-Carpet Style Moments

From crystal-trimmed Jimmy Choo sandals to metallic pumps, Upton’s footwear often provides the finishing detail to her red-carpet looks. These appearances highlight her standout designer shoes and the outfits she wore with them.