How Kendall Jenner Styled Alexander Wang’s Mascha Boots to Save Y2K Vintage

In February 2020, Kendall Jenner wore two memorable pairs of knee-high boots during Fashion Month appearances in London and New York, illustrating a styling formula she returned to throughout the season.

Whether paired with archival Jean Paul Gaultier separates or an oversized Balenciaga shearling coat, structured boots provided the visual foundation that balanced her vintage-inspired clothing.

Kendall Jenner arrives at Renell Medrano’s PAMPARA exhibition preview in London wearing an archival Jean Paul Gaultier butterfly-print ensemble, finished with a vintage Louis Vuitton Monogram Eva clutch and glossy Alexander Wang Mascha knee-high boots on February 17, 2020, in London (Credit: Instar / WENN)

At Renell Medrano’s PAMPARA exhibition preview in London on February 17, Jenner revisited Jean Paul Gaultier’s celebrated early-2000s butterfly-print collection, wearing a sheer lace-up top with a coordinating high-waisted maxi skirt.

She finished the look with a vintage Louis Vuitton Monogram Eva clutch and Alexander Wang Mascha stretch-vinyl knee boots, whose square toe, metallic toe bar, chunky block heel, and slim shaft gave the flowing silhouette a sharper, architectural finish.

A closer look at Kendall Jenner’s early-2000s Jean Paul Gaultier butterfly-print top highlights the lace-up front and semi-sheer construction that defined one of the designer’s most recognizable archival motifs

Rather than disappearing beneath the skirt, the boots anchored the outfit. Their clean geometry contrasted with Gaultier’s fluid butterfly print, showing how Jenner often used structured footwear to keep archival Y2K fashion feeling modern instead of costume-like.

The Alexander Wang Mascha boots originally retailed for approximately $750–$850 through luxury retailers including Farfetch, SSENSE, and HBX. They have since been discontinued and are no longer available from Alexander Wang or primary luxury retailers. Today, archival pairs are found almost exclusively on resale marketplaces such as eBay, The RealReal, Vestiaire Collective, and Grailed, where prices generally range from $250 to $550, depending on the material, condition, and rarity.

Their defining features—including the stretch-vinyl or leather shaft, square toe, chunky 100 mm block heel, inner ankle zip, and distinctive metallic toe bar—continue to make them one of Alexander Wang’s most recognizable boot designs from the late 2010s.

Alexander Wang’s Mascha knee-high boots feature a square toe, stretch patent-vinyl shaft, chunky block heel, inner ankle zips, and the signature metallic toe-bar detail that distinguishes the design

Earlier in February, Jenner demonstrated the same styling approach while arriving at the Longchamp Fall/Winter 2020 show during New York Fashion Week.

Instead of archival mesh and prints, she relied on dramatic outerwear—a black dyed lamb-shearling Balenciaga coat—but once again chose structured knee-high boots to ground the outfit. The recurring footwear choice became one of the defining elements of her Fashion Month wardrobe.

Earlier that month at New York Fashion Week, Kendall Jenner balanced a voluminous Balenciaga dyed lamb-shearling coat with another pair of structured knee-high boots, reinforcing the footwear silhouette that became a hallmark of her February 2020 wardrobe on February 8, 2020, in New York City

Throughout February 2020, Jenner consistently paired floor-length skirts, oversized coats, and vintage pieces with structured knee-high boots featuring square toes, substantial heels, or metallic hardware. The footwear added definition to otherwise fluid silhouettes and reflected a broader shift toward architectural accessories that was emerging on runways at the time. Looking back, these appearances capture an early example of the Y2K revival that would soon dominate luxury fashion.

How Kendall Jenner Made Architectural Boots Part of Her Signature Style

The Mascha boots were not an isolated experiment. Across airport arrivals, Fashion Week appearances, and off-duty outings, Kendall Jenner repeatedly chose boots with squared shapes, metallic hardware, cutout heels, and other sculptural details to bring structure to relaxed layers and vintage-inspired clothing.