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17 of the most daring outfits Kylie Jenner has ever worn

17 of the most daring outfits Kylie Jenner has ever worn
LifeThelife1 min read
Kylie Jenner is known for taking risks with her fashion choices.C Flanigan/Kevin Tachman/Getty Images/@kyliejenner/Instagram
  • Kylie Jenner is not afraid to embrace daring looks.
  • The youngest of the Kardashian-Jenner family is known for taking risks when it comes to her style.
  • Here are some of Jenner's most risqué fashion choices over the years.

Kylie Jenner arrived at the 2015 GQ and Giorgio Armani Grammys after-party wearing a sparkly dress that was designed with midriff cutouts.

Kylie Jenner arrived at the 2015 GQ and Giorgio Armani Grammys after-party wearing a sparkly dress that was designed with midriff cutouts.
Kylie Jenner attends the GQ and Giorgio Armani Grammys after-party in 2015.      Joe Scarnici/Getty Images for GQ

She looked edgy at the 2015 American Music Awards in a leather Bryan Hearns dress.

She looked edgy at the 2015 American Music Awards in a leather Bryan Hearns dress.
Kylie Jenner at the 2015 American Music Awards.      C Flanigan/Getty Images

Jenner wore a two-piece outfit with sheer detailing throughout the top and skirt to an after-party in 2016.

Jenner wore a two-piece outfit with sheer detailing throughout the top and skirt to an after-party in 2016.
Kylie Jenner at the 2016 InStyle and Warner Bros. Golden Globes after-party.      Jon Kopaloff/FilmMagic/Getty Images

She attended her first Met Gala in 2016 wearing a sparkly Balmain gown with cutouts along her waist.

She attended her first Met Gala in 2016 wearing a sparkly Balmain gown with cutouts along her waist.
Kylie Jenner at the 2016 Met Gala.      Taylor Hill/FilmMagic

She wore this custom-made LaBourjoisie gown with a thigh-high slit and plunging neckline to NBC's Golden Globes after-party in 2017.

She wore this custom-made LaBourjoisie gown with a thigh-high slit and plunging neckline to NBC
Kylie Jenner at the 2017 NBCUniversal Golden Globes after-party.      Jerod Harris/WireImage/Getty Images

Jenner arrived at Marie Claire's Image Maker Awards in 2017 wearing a purple Balmain gown that was designed with sheer cutouts along the sides of the skirt.

Jenner arrived at Marie Claire
Kylie Jenner at the 2017 Marie Claire Image Makers Awards.      Steve Granitz/WireImage/Getty Images

Jenner wore a see-through Versace dress to the 2017 Met Gala.

Jenner wore a see-through Versace dress to the 2017 Met Gala.
Kylie Jenner at the 2017 Met Gala.      Karwai Tang/WireImage

She chose a bold look for the 2019 Met Gala. Jenner wore a purple Versace dress that was designed with a see-through skirt and feathers.

She chose a bold look for the 2019 Met Gala. Jenner wore a purple Versace dress that was designed with a see-through skirt and feathers.
Kylie Jenner at the 2019 Met Gala.      Kevin Tachman/Getty Images

After wearing that over-the-top purple Versace gown, Jenner changed into a sparkly blue dress with a sheer skirt from the same designer.

After wearing that over-the-top purple Versace gown, Jenner changed into a sparkly blue dress with a sheer skirt from the same designer.
Kylie Jenner in NYC after the 2019 Met Gala.      Robert Kamau/GC Images

Jenner wore a gold J'Aton Couture one-shoulder dress with a thigh-high slit to Hailey Baldwin and Justin Bieber's wedding. She accessorized her look with Stuart Weitzman heels and a Judith Leiber Couture butterfly-shaped bag.

Jenner wore a gold J
Jenner shared a photo of the dress she wore to the October 2019 wedding on Instagram.      https://www.instagram.com/p/B3FCf7eHzDy/?utm_source=ig_embed

At Diddy's 50th birthday party, Jenner turned heads in a sparkly black Balmain gown with a hip-high slit and deep-plunging neckline.

At Diddy
Kylie Jenner and Khloé Kardashian at Diddy's 50th birthday party in 2019.      Kevin Mazur/Getty Images

In March 2020, Jenner matched her best friend, Anastasia "Stassie" Karanikolaou, in a see-through Jacquemus dress. They both paired the dress with coordinating earrings and shoes from the same designer.

In March 2020, Jenner matched her best friend, Anastasia "Stassie" Karanikolaou, in a see-through Jacquemus dress. They both paired the dress with coordinating earrings and shoes from the same designer.
Kylie Jenner and Anastasia "Stassie" Karanikolaou on vacation in March 2020.      https://www.instagram.com/p/B9UnlQOnkOY/?utm_source=ig_embed

During a vacation to Utah in July of 2020, Jenner wore a ruched orange dress with a single-strap top made from mesh from the Black-owned and London-based label LoudBrand Studios.

During a vacation to Utah in July of 2020, Jenner wore a ruched orange dress with a single-strap top made from mesh from the Black-owned and London-based label LoudBrand Studios.
Jenner during a July 2020 vacation at Utah's luxury Amangiri Resort.      @kyliejenner/Instagram

On the same trip, Jenner wore a $1,780 Rick Owens gown that was designed with mesh fabric around the waist to give it that semi-sheer look. She dressed it down by pairing it with combat boots.

On the same trip, Jenner wore a $1,780 Rick Owens gown that was designed with mesh fabric around the waist to give it that semi-sheer look. She dressed it down by pairing it with combat boots.
Jenner during a July 2020 vacation at Utah's Amangiri Resort.      @kyliejenner

Jenner and Karanikolaou had another twinning moment in these $275 fishnet minidresses from TLZ L'Femme.

Jenner and Karanikolaou had another twinning moment in these $275 fishnet minidresses from TLZ L
Jenner shared a photo of her and Anastasia "Stassie" Karanikolaou wearing coordinating looks on Instagram in August 2020.      @kyliejenner/Instagram

In August, Jenner showed off the $118.64 halter-style Farai London dress she wore while on vacation in Turks and Caicos.

In August, Jenner showed off the $118.64 halter-style Farai London dress she wore while on vacation in Turks and Caicos.
Jenner shared the dress she wore while on vacation in Turks and Caicos on Instagram in August 2020.      @kyliejenner/Instagram

In September, Jenner shared a never-before-seen photo of herself wearing a see-through Maisie Wilen turtleneck and the matching leggings.

In September, Jenner shared a never-before-seen photo of herself wearing a see-through Maisie Wilen turtleneck and the matching leggings.
Jenner posted this outfit photo on Instagram in September 2020.      https://www.instagram.com/p/CE2ZJH6nlSt/?utm_source=ig_embed

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