When it comes to mastering off-duty model style, Kendall Jenner often leans into high-fashion collaborations and statement footwear.
A prime example of this aesthetic was captured on May 1, 2018, in West Hollywood, when Kendall and Kourtney Kardashian stepped out at The Troubadour to support musical artist Harry Hudson.
Kendall Jenner leads the way in ripped black jeans and sleek Givenchy croc-embossed ankle boots, while Kourtney Kardashian follows in statement trousers and dark footwear as the sisters arrive at The Troubadour in West Hollywood on May 1, 2018 (Credit: WENN)
Kendall’s ensemble centered on a white cotton T-shirt from the Calvin Klein 205W39NYC collection—part of the brand’s multi-year partnership with the Andy Warhol Foundation.
Kendall Jenner’s Calvin Klein 205W39NYC x Andy Warhol Foundation ‘Dennis Hopper’ T-shirt
The “Dennis Hopper” photographic print added a cinematic edge to her ripped black denim, but the real focal point was her choice of footwear.
She anchored the look with Givenchy croc-stamped calfskin ankle boots, featuring a distinct side-zip and semi-attached tongue that elevated the casual attire.
Kendall Jenner’s croc-embossed Givenchy ankle boots place her firmly in a wider celebrity movement embracing textured, high-impact leather footwear. Similar statements have appeared across red carpets and fashion campaigns, from Winnie Harlow’s striking croc-effect Jimmy Choo boots paired with a sculptural Marine Serre look, to Kim Kardashian’s sleek croc-embossed Stuart Weitzman boots, which highlight how embossed leather adds depth and polish to minimalist styling.
Kendall Jenner keeps things effortlessly cool in a Calvin Klein 205W39NYC x Andy Warhol Dennis Hopper T-shirt, distressed black jeans, and sleek Givenchy side-zip ankle boots as she steps out in West Hollywood
Kourtney Kardashian opted for a contrasting texture, pairing a white crop top with newspaper-print Moschino trousers and a sleek black leather coat.
Together, the duo showcased how to blend streetwear basics with luxury accessories for a timeless evening look.
Kourtney Kardashian in a white crop top paired with a black leather coat
We already knew that Kendall is a fan of the American artist, director, and producer. Three years earlier, she visited an Andy Warhol exhibit in London and uploaded a photo of her favorite piece to Instagram.
Calvin Klein 205W39NYC x Andy Warhol Foundation Dennis Hopper T-shirt
Kendall Jenner’s Footwear-First Style, Beyond One Night Out
From off-duty street style to red-carpet minimalism, Kendall Jenner consistently uses footwear to anchor her looks—whether she’s stepping out in Paris, navigating airport terminals, or making a quiet statement in sculptural heels.
For readers looking to explore how her shoe choices shape her fashion identity over time, these standout moments on Your Next Shoes offer a deeper look at the styles, silhouettes, and designers that define her approach to modern dressing.
👠 Explore Kendall Jenner’s Best Shoe & Style Moments on Your Next Shoes:
- 👢 Kendall Jenner’s Paris Street Style in Sandro “Amele” Boots — street-style chic from Paris Fashion Week featuring her go-to ankle boots.
- ✈️ Kendall Jenner’s Effortless LAX Look in Sandro “Amele” Ankle Boots — a minimalist airport outfit anchored by statement footwear.
- 📏 Kendall Jenner’s Height & Heels Explained — a roundup of her iconic shoe choices from heels to boots and beyond.
- 👡 Kendall Jenner’s La Perla Moment with Gianvito Rossi “Carlyle” Sandals — a red-carpet look defined by minimalist stiletto sandals.
- 👠 Kendall Jenner’s Jacquemus & Manolo Blahnik Shoe Moments — retrospectives on early shoe highlights like classic pumps.
- 🖤 Kendall Jenner Masters Power Dressing with The Row Loafers — a Paris street-style moment blending tailoring and sleek loafers.