Not even her episode of Life in Looks can keep Kylie Jenner from taking a shot at her older sister, Kendall Jenner.
“Wow, Kendall’s feet look huge here,” Kylie laughs, looking at a photo from the 2007 premiere of Keeping Up With the Kardashians. While she notes that the ballet flats were very on-trend, Jenner doesn’t exactly remember why she picked out her pale pink dress. “My mom probably picked this out for me,” she says.
While she got her sisterly cracks in, Jenner is also down to poke fun at herself. “I couldn’t tell you what my thought process was here,” she says of a 2015 errands outfit—a cropped white long-sleeve, black leggings, chunky sneakers, and a white baseball cap over her turquoise bob. “I still have this wig, actually. My daughter loves to put it on and run around the house,” she says. “This feels very King Kylie to me.”
Of course, no Life in Looks is complete without the Met Gala carpet. “This is one of my favorite looks—still—of all time,” she says of the lavender Versace showgirl dress (and matching wig) she wore to the 2019 Met, Camp: Notes on Fashion. “I think that it’s perfect.”
Even off the Met carpet, Jenner is no stranger to outré fashion moments. Take spring 2023 couture week, when she arrived at the Schiaparelli couture show with a faux lion’s head on her chest. “I’m a Leo and I think he wanted me to wear the lion dress,” she says. “I love taking risks in fashion, and this is definitely a huge risk, but I think it’s fab.”
Though Jenner actually made her runway debut in 2011 for Avril Lavigne’s clothing line, Abbey Dawn, she walked her first show as an adult when she closed Coperni’s spring 2025 show at Disneyland Paris. While she had no nerves back in 2011, this was a different story. “I think I knew that if my daughter was there, sitting in the audience and I flew her all the way out here to see me, that I wouldn’t get cold feet and not do it,” she says. “She really gave me the confidence.”
Here, see Kylie Jenner’s Life in Looks, from her King Kylie Era to her many haute couture moments.
Director: Jean Estene
Director of Photography: Amina Zadeh
Editor: Michael Suyeda
Producer: Chase Lewis
Creative Production Coordinator: Anisa Kennar
Assistant Camera: Elizabeth Coggins
Gaffer: Nick Schulte
Audio: Gloria Marie
Production Assistants: Jordan Brown, Comfort Abiodun, Fernando Barajas
Production Coordinator: Tanía Jones
Production Manager: Anakha Arikara
Line Producer: Natasha Soto-Albors
Assistant Editor: Andy Morell
Post Production Coordinator: Holly Frew
Supervising Editor: Kameron Key
Post Production Supervisor: Alexa Deutsch
Global Video Director: Lauren Mendoza
Executive Producer: Rahel Gebreyes
Senior Director, Digital Video: Romy van den Broeke
Senior Director, Programming: Linda Gittleson
VP, Video Programming: Thespena Guatieri
