Kylie Jenner rarely hits the red carpet, but when she does, she pulls out all of the stops to make it memorable. Her celebrity status gives her access to the top stylists and a glam squad to make sure her looks are on point. From movie premieres to award shows, Kylie's looks are a group effort. And now that she is coupled up with rapper Travis Scott, there are more opportunities for her to show up and show out on the music scene. Kylie delivered that wow factor at the 2019 Grammy Awards on Sunday with a pink look that got people talking.
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She wore a pink Balmain couture jumpsuit with statement sleeves, which had built-in gloves for a super glamorous touch. It also had a jumbo belt with silver accents that highlighted her waist, despite the abundance of fabric. It looked a little too big for her and plenty of critics dragged her over the fashion-forward look. It didn't help that Kylie didn't look to happy on the red carpet. However, Kylie's beauty look was on point as usual. Her playful updo and neutral makeup were the perfect choices for her outfit.
Being worth nearly $1 billion doesn't mean you'll always get it right in the style department. But Kylie's red carpet experiments don't always backfire. Here are some of her most insane looks over the years that prove that some you win and some you lose, no matter how rich you are.
Kylie Jenner made a statement in Balmain Couture at the Grammys.
It's definitely not the Kylie that we're used to. The young mogul is used to more figure-hugging silhouettes or showing way more skin.
This is peak edgy Kylie.
Kylie turned 18 in 2015 and all bets were off. She hit the 2015 American Music Awards in leather and chainmail. The sexy dress was by Bryan Hearns.
Kylie didn't wear just any black dress to the 2018 Met Gala.
She brought a futuristic vibe to the event with her look. The strapless Alexander Wang gown, rhinestone stockings, and blinged out glasses were the right amount of extra for the star.
Kylie is no stranger to a naked dress.
She chose a heavily embellished one by Versace for the 2017 Met Gala. Her sleek platinum blond bob made sure her beatuy look was as bold as her dress.
Beauty was pain for Kylie in this look.
The Balmain gown she wore to the 2016 Met Gala was dripping in crystals, but that amount of shine came at a price. The dress made her bleed! Kylie posted a picture of scratches on her leg on Snapchat. Funny enough, Kylie wasn't mad about it. "It was worth it though," she wrote.
Kylie has a clear thing for beaded gowns.
She sparkled at a Grammys after party in 2015 with a Steven Khalil sheer gown. It allowed Kylie to show extra skin thanks to the cutouts above the hip.
Kylie was practically a gold statue on this red carpet.
Kylie wore a gold sequin Shady Zeineldine gown to the 2015 ESPYs. She made sure no one would miss her with that gilded number.
Remember way back when Kylie's loudest statement was her colorful hair?
You don't need anything else when you've got mint green hair like she did on this red carpet in 2015. Her understated matching set let the hair steal the show.
Kylie has come a LONG way from this 2015 red carpet moment.
We think that even she would agree that she was doing too much with this look. The naked dress, nude underwear, suede jacket, mint green bob, and lip filler was totally over the top.
This was another red carpet look where the hair stole the show.
Again, we bet Kylie doesn't consider this green bob she wore to the 2014 Billboard Awards a highlight in her style evolution. It was not her best look, but she has made way better choices over the years.
Kylie looked like was ready for prom at this event.
She wore this Labourjoisie set to a 2016 Golden Globes afterparty. The voluminous skirt and dazzling embellishments made this a rare princess moment for Kylie.
This look was insane for Kylie.
The nude dress by designer August Getty that she wore to Rihanna's 2nd Annual Diamond Ball in 2015 was a rare understated choice. The train still added drama, which we know Kylie can't resist.
Kylie hit the annual Harper's Bazaar Icons party in 2016 with a bold Balmain mini-dress.
The pink design had more pearl accents and tassels than one could ever need. Kylie's platinum hair delivered another heaping dose of extra.
Kylie's hair stole the show once again at the 2015 MTV Video Music Awards.
She wore a beige Balmain mini-dress to the show with coordinating heels. However, her bangs were all we could see. The dress and hair made her look much older than she was at the time.
We couldn't do a list like this without a major throwback.
Kylie looked so different in 2011 when this picture was taken! It is astounding the difference a few years, success, cosmetic enhancements, and a powerful glam squad can make.
