Kendall Jenner Modernizes ’90s Minimalism: From Ganni Cowboy Boots to “Ugly Sandals”

In May 2021, Kendall Jenner stepped out in West Hollywood, providing a masterclass in how to modernize the most enduring fashion archetypes of the 1990s.

While her appearance coincided with the Friends reunion special, the outfits she debuted at Petite Taqueria serve as a permanent blueprint for styling “90s minimalism” with contemporary footwear.

Kendall Jenner Modernizes a ’90s Little Black Dress With Ganni Cowboy Boots

Kendall Jenner updates Rachel Green’s ’90s minimalism by pairing a slinky black slip dress with statement cowboy boots while grabbing tacos in West Hollywood on May 27, 2021 (Credit: Instar / WENN)

The 818 Tequila founder proved that the “Rachel Green” aesthetic—specifically the slinky, square-neck LBD—remains a wardrobe staple because of its versatility.

However, rather than leaning into the era’s traditional strappy heels, Jenner pivoted to a rugged Western silhouette to create a high-low contrast that works in any decade.

She put her toned arms on display in the satin number, which features a halter-style square neckline with spaghetti straps and side slits that let her show off her long, slim pins.

In addition, the frock was cinched at the waist with a black string, which highlighted her slim figure.

Kendall Jenner gives a casual daytime edge to a sleek black slip dress by grounding the look with glossy Western-style cowboy boots during a West Hollywood outing in May 2021 (Credit: Instar / WENN)

The 818 Tequila founder wore her hair loose with a center parting and covered her face with a pair of Dmy by Dmy Valentina sunglasses and a black face mask.

She kept her look minimal, styling it with just a pair of stud earrings and a black “Half Moon” bag from The Row.

Available for $1,290 at Mytheresa, her ‘90s-style calf leather bag has a streamlined asymmetric silhouette, a top-zip closure, and a flat shoulder strap.

Kendall Jenner hides her face behind a pair of Dmy by Dmy sunnies and a face mask (Credit: Instar / WENN)

While you can pair a little black dress with just about anything—from flat sandals and sneakers to high heels, Kendall opted for cowboy boots.

She chose the now-sold-out “High Texas” Western boots from Copenhagen-based brand Ganni.

Made in Portugal, these cowhide leather boots feature Western stitching, a large butterfly detail at the back, the brand’s logo embroidery on the pull tabs, and 2-inch heels with a rubber patch on the soles.

Kendall Jenner steps out in Ganni’s “High Texas” Western boots, using the glossy cowboy silhouette to add edge and contrast to her sleek, minimalist black dress (Credit: Instar / WENN)

Kendall Jenner Embraces ’90s Menswear and the “Ugly Sandal” Trend With Alias Mae Slides

A day before sporting her Rachel Green-inspired outfit, Kendall was seen recreating another look from another Friends character.

This time, she wore a ‘90s tuxedo vest similar to Chandler Bing’s signature outfit from Friends.

Kendall Jenner puts a modern spin on Chandler Bing’s ’90s menswear aesthetic by pairing a tailored vest and relaxed trousers with chunky “ugly” slide sandals while out for lunch in Los Angeles on May 26, 2021 (Credit: Instar / WENN)

Borrowing from men’s fashion, Hailey Bieber’s best friend wore a gray vest with tortoiseshell buttons from Italian men’s brand Daniele Alessandrini.

Continuing with her 1990s look, she paired her vest with black baggy pants from Fiona O’Neill, an eponymous conceptual womenswear label founded in 2019.

Kendall Jenner leans into relaxed menswear tailoring with a Daniele Alessandrini vest and Fiona O’Neill baggy trousers, grounding the look in chunky slide sandals for an effortless, off-duty finish (Credit: Instar / WENN)

The KUWTK star skipped the jewelry, save for a tiny pair of gold hoop earrings. She then hid her eyes behind her Dmy by Dmy sunglasses and wore a bare-faced makeup look.

She carried her stuff in a large, colorful “Idunn” checked bag from Stine Goya, which she slung over her shoulder.

Kendall Jenner adds a playful pop of color to her neutral menswear-inspired outfit with a large, checkered Stine Goya tote slung casually over her shoulder (Credit: Instar / WENN)

To complete her trendy look, Kendall opted for the ugly sandal silhouette from Alias Mae, a Melbourne-based footwear brand known for its contemporary and refined designs.

Kendall Jenner leans into the “ugly sandal” trend by finishing her relaxed menswear look with Alias Mae Paris slide sandals, balancing comfort-driven design with effortless street style (Credit: Instar / WENN)

She wore the “Paris” sandals, which feature lightly padded twisted straps made from supple natural leather and rubber soles.

A chunky two-strap Alias Mae Paris sandal silhouette made from leather with rubber soles

Why Ganni and “Ugly Sandals” Continue to Shape Modern Celebrity Footwear

From runway-driven labels like Ganni to the rise of comfort-first “ugly sandals,” today’s celebrity style proves that footwear—not trends alone—defines how fashion evolves off the red carpet.