Kendall Jenner has never missed a style beat—from early red carpet looks with Kylie to headlining her own tequila brand in sky-high heels.
We’re looking back at one of her most glamorous moments from her 818 Tequila celebration—and some unforgettable throwback fashion that proves her shoe game has always been strong.
Beachside Chic: Kendall Jenner’s Head-Turning Look at the 818 Tequila Party
In August 2021, Kendall Jenner and her 818 tequila brand hosted a fun beachside party at Sunset Beach Hotel on Shelter Island in New York.
Kendall Jenner celebrates her 818 Tequila at Sunset Beach Hotel on Shelter Island, New York, on August 19, 2021, wearing a green ruched Sanda Simona Studio dress, joined by Luka Sabbat, Derek Blasberg, and Karlie Kloss in a blue off-the-shoulder ribbed knit dress (Credit: MEGA / WENN)
The Jacquemus model was joined by Karlie Kloss, Arab model Fai Khadra, cultural influencer Luka Sabbat, fashion blogger Derek Blasberg, and her boyfriend Devin Booker.
“Devin led Kendall through the crowd upon arrival and led her to her seat,” an eyewitness told Us Weekly. “They kept making eye contact throughout the night and never strayed far away from each other.”
Boyfriend Devin Booker supported Kendall Jenner as she celebrated her 818 Tequila at a rooftop party in New York (Credit: MEGA / WENN)
“[Devin] seemed very close and friendly with her friends,” the insider added about the 24-year-old Phoenix Suns basketball player. “At the end of the night, they walked out together hand in hand with nothing but smiles.”
Sipping on hand-crafted tequila from Jalisco, México, they celebrated the success of the start-up spirits brand that launched in May and recently hit shelves in New York.
Kendall celebrated her 818 Tequila in a green Sanda Simona Studio draped mid-length dress at a rooftop party in New York (Credit: MEGA / WENN)
The 818 Tequila founder stunned in a green asymmetric jersey midi dress by Sanda Simona Studio. The dress featured twisted construction, flattering front gathers, and a subtle back cutout that added just the right amount of edge.
She completed the look with sculptural Cult Gaia Aria earrings and elegant Bottega Veneta pumps. Unfortunately, clear photos of her shoes from the event were limited, but knowing Kendall, they were undoubtedly just as striking as the rest of her ensemble.
Long before she was hosting glamorous tequila parties in designer heels, Kendall was already carving out her place in the fashion world. One memorable throwback moment? A red carpet appearance with sister Kylie back in 2012 that hinted at the confident style icon she’d become.
Boots, Leather, and Teen Confidence: Kendall and Kylie Jenner’s Bold 2012 Red Carpet Moment
Kylie and Kendall Jenner at KIIS FM’s 2012 Jingle Ball held at Nokia Theatre L.A. Live in Los Angeles on December 3, 2012 (Credit: WENN)
Showing she’s got the Kardashian/Jenner good looks, in December 2012, the then-17-year-old Kendall Jenner flaunted her long legs in a gray top, a leather miniskirt, and a slicked-back ponytail at KIIS FM’s 2012 Jingle Ball at LA’s Nokia Theatre.
Kendall Jenner showed off her long legs in a sleek black leather mini skirt, cutout-shoulder gray top, and statement-making studded suede ankle boots that added edge and height to her red carpet look (Credit: WENN)
Kendall Shows Off Her Model Legs in a Leather Miniskirt and Suede Ankle Boots
Compared to Kylie, Kendall seems to have the “model” body type and flaunts an impressive pair of long legs. No wonder she’d want to show off her assets on a night like this.
I love her choice of clothes, especially her high-waist leather bodycon skirt and zip suede ankle boots. The skirt makes her body look even more slender, and her legs look longer. What do you think?
Kendall Jenner showcases style with a leather mini skirt at the KIIS FM 2012 Jingle Ball (Credit: Apega / WENN / FayesVision)
Kylie Jenner Goes Feminine-Chic in a Pleated Leather Skater Skirt and Tee
Next stop, the then-15-year-old Kylie opted for a more feminine-chic ensemble consisting of a simple tee and a pleated skater leather miniskirt.
Kylie Jenner combines feminine chic with edge in a pleated leather mini skirt at the 2012 KIIS FM Jingle Ball (Credit: Apega / WENN / FayesVision)
She pulled this look off with her more curvaceous body, but perhaps she could’ve chosen strappy shoes instead of basic pumps. That would have helped elongate her legs.
Fashion Spotlight: Kendall and Kylie Jenner at the KIIS FM 2012 Jingle Ball, Los Angeles on December 3, 2012 (Credit: Apega / WENN / FayesVision)
Kendall Elevates Her Look With $2,500 Azzedine Alaïa Studded Suede Ankle Boots
Kendall has a taste for expensive designer things, so she finished her casual outfit with Azzedine Alaïa stud and zip suede ankle boots, which cost approximately $2,500!
For readers intrigued by the craftsmanship and legacy behind Kendall’s statement boots, explore our in-depth feature on Azzedine Alaïa’s enduring impact on haute couture.
Kendall Jenner’s Azzedine Alaïa studded suede ankle boots—crafted in Italy with intricate latticework and luxe materials—show why designer footwear comes at a premium (Credit: WENN)
Whether she’s commanding the red carpet or keeping it casual off-duty, Kendall Jenner consistently delivers head-turning fashion—and her footwear is no exception. From luxe heels to laid-back sneakers, here are some of her most unforgettable shoe moments.
Stepping Into Style: Kendall Jenner’s Iconic Footwear Moments
Kendall Jenner consistently turns heads with her impeccable shoe choices, seamlessly blending high fashion with street style. As she once said, “I guess my style’s a little edgy but comfortable,” and her footwear moments—from luxury heels to casual sneakers—perfectly reflect that balance. Here are some of her most memorable looks:
Power Dressing in Bottega Veneta and The Row Loafers
- Event: Paris Fashion Week
- Outfit: Kendall showcased a bold mix of stripes and checks in a Bottega Veneta suit.
- Footwear: She completed the look with sleek loafers from The Row, epitomizing minimalist elegance.
- More Details: Kendall Jenner’s Parisian Power Look
Jimmy Choo’s Spring 2023 Campaign Star
- Event: Jimmy Choo Spring 2023 Campaign
- Outfit: Kendall donned a purple minidress against the NYC skyline backdrop.
- Footwear: She wore the Diamond Talura 100 Pumps in Wisteria, adding a touch of glamour to the ensemble.
- More Details: Inside Kendall’s Daring Jimmy Choo Campaign
Casual Chic in Adidas Stan Smith Sneakers
- Event: Boating in Cannes
- Outfit: A floral Zimmermann romper paired with an oversized Hermès Birkin bag.
- Footwear: Kendall opted for classic white Adidas Stan Smith sneakers, blending comfort with style.
- More Details: Kendall’s Nautical Sneaker Style
UGG Boots for a Rainy Day in Beverly Hills
- Event: Casual Outing in Beverly Hills
- Outfit: Black leggings and a blue hoodie jacket.
- Footwear: Chestnut UGG Classic Ultra Mini boots paired with high white socks, showcasing her laid-back style.
- More Details: Kendall’s Cozy Rainy Day Look
Model-Off-Duty in ASICS Sneakers
- Event: Pilates Session in Los Angeles
- Outfit: Sporty ensemble featuring a bold red jacket.
- Footwear: ASICS sneakers, highlighting her commitment to both fitness and fashion.
- More Details: Kendall’s Athleisure Aesthetic
From high-fashion campaigns to casual outings, Kendall Jenner’s shoe choices continue to inspire fashion enthusiasts worldwide.