In August 2019, Kylie Jenner made it a glamorous family affair on the red carpet at the Santa Monica premiere of Look Mom I Can Fly, the Netflix documentary spotlighting partner Travis Scott’s meteoric rise to fame.
Joined by their daughter Stormi Webster—making her adorable red carpet debut—Kylie wowed in a sleek, backless white dress and timeless Manolo Blahnik BB heels. Stormi, already a scene-stealer, matched her mom’s palette in a camouflage set and fresh white mini sneakers.
The stylish family moment was just one of several that month. Not long after, Kylie’s father, Caitlyn Jenner, made headlines of her own at the Comedy Central Roast of Alec Baldwin, bringing her own brand of elegance—and sky-high heels—to the red carpet.
Inside Travis Scott’s ASTROWORLD Journey: From Studio to Streaming
Stormi Webster stole the spotlight in an adorable camouflage-print outfit paired with crisp white mini sneakers, matching her mom Kylie Jenner’s sleek white dress and dad Travis Scott’s sharp brown suit
Directed by White Trash Tyler, the documentary revolves around Travis’s rise to fame and his time creating and releasing his third album, ASTROWORLD.
Stormi Webster, Travis Scott, and Kylie Jenner at the premiere of Look Mom I Can Fly at the Barker Hangar in Santa Monica, California, on August 27, 2019 (Credit: Avalon / WENN)
Stormi Webster made an adorable red carpet debut in crisp white mini sneakers and a camouflage set, perfectly complementing her mom’s effortlessly chic look.
Kylie Jenner Elevates Her Look in Iconic Manolo Blahnik BB Heels
Kylie turned heads in a curve-hugging white dress paired with iconic Manolo Blahnik BB heels—sleek pointed-toe pumps originally introduced in 2008 and named after French style muse Brigitte Bardot.
👠 Explore Iconic BB Moments in Celebrity Style:
- ✨ Kendall Jenner’s NYC Style: How She Makes Manolo Blahnik BB Pumps a Wardrobe Staple – A fashion‑week‑ready styling of the versatile suede BB pumps.
- 💥 Melania Trump’s Iconic Manolo Blahnik BB Pumps Steal the Show – A timeless inauguration appearance featuring classic pointed‑toe BB stilettos.
- 🌿 Reese Witherspoon’s Chic Lunch Look: Floral Sweater & Manolo Blahnik BB Heels – Reese pairs emerald-green BB pumps with relaxed yet polished daytime styling.
- 💃 Eva Longoria Shoots New Show ‘Type A’ in Manolo Blahnik BB Pumps – Behind‑the‑scenes glam with crocodile‑embossed BB pumps on set.
- 👑 Elizabeth Hurley Stuns in Nude Trench Coat and Manolo Blahnik Pumps – A monochrome moment with nude BB pumps for a sleek promotional look.
- 🛍️ Rosie Huntington‑Whiteley in Manolo Blahnik ‘BB’ Suede Point‑Toe Pumps – Styling street shopping with suede BB pumps paired with designer casuals.
- 🎨 Design Your Own Pair of Manolo Blahnik Pumps! – A style enthusiast’s guide to customizing BB pumps via made‑to‑order options.
- 🛠️ Manolo Blahnik: Fascinating Man and Brand Behind Masterful Shoemaking – Deep dive into the craftsmanship and legacy of Blahnik’s signature styles like the BB pump.
Kylie Jenner exudes elegance in a form-fitting white dress paired with classic pointed-toe pumps, accentuating her sophisticated style
Known for their timeless silhouette, these stiletto pumps are a symbol of refined elegance and a celebrity favorite, crafted with exquisite attention to detail in materials ranging from suede to satin.
Kylie’s choice in BB heels added an air of classic glamour to the modern, minimalist ensemble.
Kylie Jenner stuns in a backless white dress, while Travis Scott complements her look in a sleek brown suit
From red carpet elegance to everyday streetwear, Kylie Jenner continues to make bold style statements with every step. Explore more of her standout shoe moments below:
👠 Dive into Kylie Jenner’s Standout Shoe Stories:
- ✨ Kylie Jenner and Timothée Chalamet Wow in Schiaparelli – Showcases Kylie’s elegant suede pointed‑toe Mary Jane mules on the red carpet.
- 💥 Kylie Jenner’s Puma ‘Fierce’ Sneakers: A Copy of Rihanna’s Fenty Kicks? – Highlights Kylie’s Puma ‘Fierce’ sneakers and the stylistic comparison to Rihanna’s line.
- 👟 Kylie Jenner Wears 3 Designer Pumps and Ends Up in Puma ‘Trinomic’ Sneakers – Details her multiple shoe changes before settling on sporty kicks.
- 🎢 Kylie Jenner’s Cozy Mommy‑and‑Me Look: How She Rocked Yeezy 500s With Baby Stormi – Captures a relaxed athleisure outfit featuring Yeezy 500 sneakers.
Kylie Jenner, nearly matching Travis Scott’s height thanks to her high heels, stuns in a backless white gown while the couple shares a kiss at the premiere
Standing at 5ft 9 ¾ (177.2 cm), Travis Scott was comfortably taller than Kylie Jenner, who stands at 5ft 6 (167.6 cm).
Even with the added boost from her high heels, the rapper’s height still gave him a noticeable edge beside his girlfriend on the red carpet.
Just weeks after Kylie and Stormi’s stylish red carpet appearance, Caitlyn Jenner brought her own dose of glamour to the spotlight—this time at the Comedy Central Roast of Alec Baldwin in Beverly Hills.
Wearing a sleek black dress and classic pointed-toe pumps, Caitlyn turned heads on the red carpet, though the attention quickly shifted from fashion to the night’s headline-making jokes.
Caitlyn Jenner and Ireland Baldwin Shine at the Comedy Central Roast of Alec Baldwin
Caitlyn Jenner stuns in a sleek black dress and matching pointy-toe pumps at the Comedy Central Roast of Alec Baldwin in Beverly Hills, California, on September 7, 2019 (Credit: WENN / FayesVision)
Wearing a black dress with matching pointy-toe pumps, Caitlyn Jenner joked about having “retired” her male genitalia after raising ten children and passionately defended herself at the end of her set.
Caitlyn Jenner, standing at 6ft 1 (185.4 cm), greets the nearly equally tall 6ft 0 (182.9 cm) Ireland Baldwin, who stuns in a satin peach dress and strappy heels that bring them even closer in height
“I’m not perfect,” she said. “I’m a person trying to figure out my life, just like everyone else. All I want is for future generations of transgender people to know that if I can find the courage to be who I am, then you can too. If you have a problem with that, then you can suck my d—. If you can find it!”
Standing at 6ft 1 (185.4 cm) and wearing a women’s US shoe size 13, Caitlyn has spoken about the challenges of finding clothes—and especially heels—that fit her tall frame and larger shoe size after transitioning.
The star-studded event drew a wide mix of celebrities, including Alec Baldwin’s daughter Ireland Baldwin, Robert De Niro, David Spade, Ken Jeong, Sean Hayes and his partner Scott Icenogle, SNL’s Chris Redd, Broad City actor Arturo Castro, YouTuber David Dobrik, model Dita Von Teese, comedian Jeff Ross, and Billy Bush.
Ireland Baldwin stuns in a peach satin wrap dress paired with platform sandals, while her father, Alec Baldwin, keeps it classic in a black tuxedo
But it was Ireland Baldwin who truly commanded attention on the red carpet, towering in strappy platform sandals and a satin peach wrap dress that highlighted her statuesque frame.
Ireland Baldwin, standing 6ft 0 (182.9 cm) and made even taller by her strappy heels, towers over her father, Alec Baldwin, as they pose together at the Comedy Central Roast