Kylie Jenner takes fashion risks like it's one of her jobs. The young mogul grew up in the spotlight thanks to Keeping up with the Kardashians and had to look the part of being reality TV royalty from a young age. Having a bunch of stylish sisters heavily connected in the fashion industry and the ability to assemble the ultimate glam squad helps. Being on the cusp of billionaire status when there is no such thing as a budget is the cherry on top. Kylie's imagination is the only limit.
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Today she is crushing red carpets and owning street style with edgy outfits that keep her in the headlines. It is hard to believe that Kylie doesn't want to be famous and that there was a point in time where playing dress up didn't feel effortless. "I see Kendall [Jenner] and Bella [Hadid] and Hailey [Baldwin], and they're just out here, like every day," she said on an episode of Life of Kylie last year. "They just put their outfits together and they're made for this, which isn't a bad thing. They look so good every day. Sometimes I wish I could do what they do. But that's not me. I don't want my picture taken. I don't want people to see what outfit I'm wearing. Every time there's paparazzi, I cover my face."
Despite what is going on behind the scenes, Kylie continues to serve looks. The older she gets, the bolder her choices seem to get. Kylie may have given birth to her baby, Stormi Webster, earlier this year but it has not slowed her fashionable roll at all. This month may go down as one of her most iconic ever thanks to her 21st birthday celebrations and her 2018 MTV Video Music Awards red carpet moments. Here's a look back at her most head-turning looks so far. We are certain that there are more to come.
–Additional reporting by Sugey Palomares
Kylie dressed like a total boss in this grown and sexy blazer dress.
Kylie Jenner stunned in an ivory Tom Ford belted mini dress at the 2018 MTV Video Music Awards. Sleek hair, matching heels, and diamonds completed the look.
She took the New York City summer streets in all leather everything.
Wearing this much black leather on a muggy summer day is definitely daring.
Kylie sizzled in a red hot mini dress.
Leave it to Kylie to shut down the sidewalk in a red Alexander Wang dress and strappy heels.
Kylie proved you don't need cleavage to have a sexy graphic T-Shirt moment.
Kylie took the look of her black tee with a neon corset design to the next level with fishnet pumps.
She celebrated turning 21 this month in a statement short jumpsuit.
Kylie partied the night away in an $8,000 custom LaBourjoisie pink jumpsuit that was bedazzled with 70,000 Swarovski crystal stones.
She kept her shoulder game strong in this stunning satin dress.
Kylie Jenner had an '80s moment for her 21st birthday family dinner. She wore a gorgeous fuschia mini dress by designer Peter Dundas and matching Olgana Paris heels.
We're sure this Alexander Wang outfit didn't make it to the gym.
Kylie added a pair of heels to take this luxury athleisure look out for a night on the town.
Kylie gave boyfriend jacket a new meaning with this oversized coat.
Wearing this coat in the Los Angeles heat should be considered a special skill.
Kylie knows the power of a special pair of sunglasses.
Kylie hit the 2018 Met Gala in a black strapless Alexander Wang gown that featured a cutout under the bust and long train. Diamond-encrusted Gentle Monster x Alexander Wang glasses made the look so her.
There is nothing subtle about a patent leather camel suit and hot pink wig.
She did it for the 'gram in this outfit this spring.
A Fendi moment for the mommy history books.
Kylie created an unforgettable moment by taking Stormi for a stroll in a Fendi print stroller while wearing a skin-tight Fendi print mini dress.
Her barely there white satin dress could double as a nightie.
Kylie knows she is far from innocent in this look.
The hardware on this outfit takes the sexy factor to 11.
Kylie wore this outfit for a night out in 2017.
Kylie wore the ultimate naked dress to the 2017 Met Gala.
Mesh, beads, fringe, and more — this nude Versace dress had it all.
Kylie showed a lot of leg in a whole new way with this purple Balmain set.
She was definitely feeling herself in this look.
Kylie's cleavage had a major moment in this white fringe jumpsuit.
She wore this for a family dinner in Costa Rica in 2017.
Forget ugly sweaters, Kylie slayed in a black sequin jumpsuit for a 2016 Christmas party.
Kardashian family functions are always glam.
Kylie got the world shook when she recreated the classic Christina Aguilera "Dirrrty" look.
She went all out in leather chaps, a bikini top, and faux piercings for Halloween in 2016. Xtina forever!
Kylie took a white tee and made it fashion with sexy additions.
If you aren't matching your over-the-knee boots to your corset, you're not doing it right.
Mixing casual and dressy pieces is signature Kylie.
This denim and glitz moment from New York Fashion Week in 2016 was everything.
She stopped traffic in red that same season.
Kylie Jenner took New York Fashion Week by storm in this flashy red and burgundy combo.
Kylie slayed in this intricate Balmain pink tassle dress.
She stole the show at a 2016 Harper's Bazaar party in the look.
You can always count on a jaw-dropping birthday look from Kylie.
She celebrated her 19th birthday in a revealing black lace jumpsuit by Balmain that hugged every curve.
She risked it all in this nude bandage jumpsuit.
Pulling off this much underboob isn't easy.
Nothing says you have arrived like leather and chain links.
Kylie did not come to play in this black leather dress by Bryan Hearns at the 2015 American Music Awards.
Nothing says Kardashian like a bandage dress.
Kylie attended the 2015 MTV Video Music Awards afterparty in a black bandage dress that left little to the imagination.
No mini dress is too short for Kylie.
For the 2015 VMA red carpet, she posed in a gold mini-dress designed by Balmain.
Kylie celebrated her 18th birthday in a sexy little white dress.
Look at those legs!
Kylie posted this provocative snakeskin yacht moment in 2015.
"Anaconda," she captioned the photo.
Kylie has been using her hair to make a statement for years.
She wore a mint bob and a sheer nude dress to the Paper Towns premiere in 2015.
She wore a daring low-cut black gown on red carpet at Sugar Factory Miami in 2015.
Kyle has clearly taken some inspiration from her older sister, Kim Kardashian.
Kylie hit a 2015 Cannes Film Festival party in a sheer white skirt and crop top.
Her mom, Kris Jenner, was also at the event and somehow didn't freak over the revealing look at the time.
Don't count on Kylie to wear a simple bikini while working on her tan.
She rocked this black cut-out swimsuit in 2015.
She wore a next-level pool party outfit at Coachella in 2015.
Kylie posed in a black catsuit with then boyfriend Tyga and sister Khloe Kardashian. Whoa!
Kylie was showing off major cleavage in this racy white jumpsuit at a launch party in 2015.
Her blue hair makes her stand out even more.
Kylie wore a seriously short striped dress to the 2015 Billboard Music Awards.
She loves showing off her legs.
Looking snatched is a must for Kylie.
Jenner looked super mature in this tight bandage dress she wore in 2015.
Wearing a sports bra as a top was one of Kylie's favorite trends back in the day.
"Can I wear a sports bra & boxers all day ugh," she captioned this photo she shared in January 2015.
Kylie looked like she stepped out in a sexy night gown at the 2014 American Music Awards.
The burgundy dress showed major cleavage and leg!
A mini dress is always a good idea in Kylie's book.
Talk about showing off legs!
