Winnie Harlow, a fashion icon known for her unconventional and unapologetic style, led the style pack in a leather Marine Serre dress and Jimmy Choo boots at the Pegasus World Cup 2025 held at Gulfstream Park in Florida. Stars like Lele Pons, Isabela Grutman, and Mike Tyson also attended the American Thoroughbred horse race event.
Harlow’s all-leather outfit is not typical of someone attending an outdoor horse race event, as the material can be extremely hot and uncomfortable. The color, however, seems fitting, in my opinion. It’s earthy and rustic, which is often associated with horseback riding.
Winnie Harlow leads the style pack in head-to-toe leather at the Pegasus World Cup 2025 at Gulfstream Park in Florida (Credit: Robert Bell / INSTARimages)
Winnie Harlow Owns the Pegasus World Cup in Jimmy Choo Croc Boots
The Canadian fashion model looked confident and runway-ready in Jimmy Choo’s brown, almost burnt orange, croc knee-high boots. She wore the “Alizze” boots, made in Italy from shiny brown cuoio croc-effect leather. You can buy them on sale at Net-a-Porter and Mytheresa.
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They have sharp, pointed toes that elongate the foot, giving it a more attractive and slender appearance. I like how their thin block heels complete the ensemble’s refined and stylish appeal while making Harlow appear taller and more confident.
Although they seem tough and opulent, these textured croc leather boots can be dressed up or down for any occasion, making them an excellent pick for anyone looking to add modern sophistication to their wardrobe.
Winnie Harlow exudes sultriness in shiny brown croc-effect leather boots by Jimmy Choo featuring pointed toes and thin block heels (Credit: Robert Bell / INSTARimages)
Why Jimmy Choo Knee-High Boots Are a Celebrity Favorite
For those captivated by Winnie Harlow’s striking ensemble, it’s worth noting that Jimmy Choo’s knee-high boots have been a favorite among fashion icons.
For instance, in the Fall 2022 campaign, Kendall Jenner showcased the brand’s bold designs, including the Blake Metallic 110mm Wedge Boots. These boots feature a distinctive sculptural heel and a sleek pointed toe, exemplifying Jimmy Choo’s commitment to sophisticated style.
Additionally, the Off-White x Jimmy Choo collaboration introduced the ‘Sara’ quilted leather boots, blending luxury craftsmanship with contemporary aesthetics. These designs highlight the brand’s versatility and appeal to those seeking both classic and avant-garde footwear options.
Exploring these collections offers a deeper appreciation of how Jimmy Choo continues to influence modern fashion with its innovative knee-high boot designs.
Winnie Harlow’s Leather-on-Leather Moment in Marine Serre
In keeping with her outfit’s earth-tone theme, Harlow paired her brown boots with a brown leather mini-dress by French designer and sustainable activist Marine Serre, renowned for her avant-garde take on high fashion.
Among her best-known designs is her crescent moon-printed clothing, as seen in Harlow’s ensemble. Often linked to Islam, the crescent moon inspired Serre’s 2016 graduation collection, Radical Call for Love, from La Cambre in Brussels. She stated that the collection wasn’t a political statement; instead, it was a response to the terrorist attacks in Paris and Brussels.
The All Over Moon Gradient design is airbrushed onto the smooth, supple sheep leather dress. Different shading intensities are used in each piece in the collection, creating a dramatic chiaroscuro effect that “adds depth, dimension, and a shimmering mercurial quality” consistent with the house’s lunar codes. It’s strapless and is finished with an asymmetric knee-grazing hem.
Winnie Harlow teams her faux croc leather boots with a brown leather Marine Serre mini-dress featuring the designer’s signature crescent moon print (Credit: Robert Bell / INSTARimages)
Marine Serre’s Signature Style: Why Celebs Can’t Get Enough
Winnie Harlow’s choice of a Marine Serre leather mini-dress at the Pegasus World Cup underscores the designer’s rising influence in celebrity fashion. Ice Spice recently turned heads in a sheer mesh ensemble adorned with Marine Serre’s signature moon print, showcasing the brand’s distinctive aesthetic.
Additionally, Jimmy Choo’s collaborations with designers like Marine Serre have blended high fashion with unique design elements, emphasizing her growing prominence in the fashion world.
Harlow, Kyle Kuzma’s girlfriend since 2020, layered the dress underneath a monochromatic patchwork lambskin leather coat, also by Marine Serre. It has a striking color-blocked paneling featuring different shades of brown, a spread collar, front press-stud closure, and a detachable self-tie belt that Winnie chose to go without.
While I like every piece of Winnie’s ensemble, I believe it might be better suited for a different setting. The coat feels too heavy for the horse race event.
Winnie Harlow layers her mini-dress underneath a monochromatic brown patchwork lambskin leather coat by Marine Serre (Credit: Robert Bell / INSTARimages)
Winnie Harlow’s Bold Accessories: The Art of Statement Styling
A maximalist in terms of fashion, Harlow added dramatic jewelry to her already eye-catching outfit. She wore a pair of unconventional resin and gold drop earrings, a thick chain necklace, and stacks of bangles on each wrist.
In line with the monochromatic theme of her outfit, she also covered her eyes with burnt orange sunglasses.
I wish she had opted for a hat typically worn to horse racing events, as it would have added a touch of flair and sophistication to her ensemble. That said, her wavy hair styled in a high ponytail looked fantastic and made her stand out beautifully.
Winnie Harlow, with Mike Tyson, styles her look with a chain necklace, dangling earrings, and stacks of bracelets (Credit: Seth Browarnik / INSTARimages)
Celebrities Prove Knee-High Boots Are a Timeless Must-Have
Transitioning from Winnie Harlow’s striking ensemble, it’s evident that knee-high boots remain a staple in celebrity fashion, offering both versatility and style. For instance, Nicole Scherzinger recently showcased a chic look by pairing a black mini dress with sleek over-the-knee boots, demonstrating how this footwear can elevate a simple outfit.
Similarly, Irina Shayk was spotted embracing a casual yet polished appearance, combining a black boyfriend shirt dress with classic riding boots during a city stroll. These instances highlight the adaptability of knee-high boots, whether aiming for a sophisticated or relaxed look.
For those interested in exploring various styles, our comprehensive guide on the history and types of knee-high boots offers valuable insights into selecting the perfect pair to complement any wardrobe.
For those inspired by Winnie Harlow’s stunning Jimmy Choo croc knee-high boots, there’s no shortage of ways to style this statement footwear. Whether you prefer sleek black for a polished touch, warm brown for a bold contrast, or a textured edge to elevate your look, Shopbop has the perfect knee-high croc boots to fit your aesthetic. Pair them with oversized sweaters and mini skirts for a sporty-chic vibe, go monochrome for an effortlessly sophisticated appeal, or embrace romantic pleats with a structured finish—these boots are as versatile as they are striking.
Croc-embossed knee-high boots styled three ways—sporty-chic with a sweater dress, sleek and monochrome, or effortlessly feminine with pleats