21 Of Kylie Jenner's Best Looks That Literally Changed The Game Of Fashion

Kylie Jenner is daring, different and arguably the most fashion-forward Kardashian-Jenner sister. She literally grew up in front of the world, from youngest reality show sister to fashion influencer among other things. Kylie took notes from her famous family and launched one of the biggest makeup brands in recent years and she helps run her fashion line, Kendall+Kylie with her sister Kendall. But Kylie isn't just into fashion she's also into makeup, but she's unlike any of her sisters. She's willing to take a fashion risk---and not just for a magazine shoot. She'll put on a wig and change her entire persona from week to week. Kim K is only doing this now, while Kylie's been doing it for years. While Kylie is proving to be getting edgier in her fashion choices, Khloe, Kourtney, and Kendall are slowly following suit.

Kylie's sister Kendall was given the “Fashion Icon of the Decade” award by Daily Front Row due to her supermodel status despite only being a model for a few years. But the honor should have gone to Kylie who not only breaks the internet on a regular basis with her fashions (she's a constant source of inspiration), but she has single-handedly changed the way people buy makeup. Her influence has also amassed her a huge fortune.

It might be hard to decide, but what are your favorite Kylie moments?

21 Kylie Jenner's A Golden Goddess

Kylie Jenner may have been at the ESPY Awards, but the entrepreneur looked like she like a golden Oscar statue at the event. Kylie stole the show from her father, Caitlyn Jenner who was honored with the Arthur Ashe Courage Award in 2015. And while Kylie was shining she says she is not as flashy as she may appear on social media.

“I'm not myself on Snapchat or Instagram. That's totally not me. I'm way flashier on Instagram and Snapchat because I feel like that's what people want to see and that's what I've always done, so I'm not going to stop. People want to see my cars and my purses. People love fashion. But that's so not me,”

she told Interview Magazine. Kylie was shining bright like a diamond as Rihanna would say.

20 And She Made Crochet Glam

Kylie knows how to work fashion. In this street style moment, the youngest Kardashian/Jenner sister wore a Yeezy bodysuit and a sheer blue crochet skirt courtesy of Balmain. She paired her ensemble with a Hermes bag and nude heels----all this to get dinner with then-boyfriend, Tyga. All the Kardashian-Jenner ladies love to wear bodysuits from Kim K. to Khloe. It appears a fashion statement that all the ladies love. Kylie was actually a model for her brother in law Kanye West's Yeezy season 1 back in 2015. At the time Kris Jenner gushed over her daughter's modeling skills, "Such a great job @kyliejenner modeling in the #KanyeWest @adidas fashion show at #NYFW !! Oh, no big deal just Anna Wintour and Kanye chillin and chatting behind you… #Yeezy #proudmama#kimdoinglastlooks," (via Cosmo).

19 But That Time She Showed Off Her Figure In A Bold Way

Kylie showed off her edgy cool style at the 2015 Billboard Awards. The reality star was a black leather striped dress from Balmain. And her legs looked long and lean paired with her high heeled caged boots also from Balmain. Kylie and her famous family are close friends with Balmain's creative director, Olivier Rousteing and often work with the brand. All the ladies love Olivier's designs. But if you notice that Kylie is a little serious on the red carpet its due to Kylie's struggle with fame. According to People Kylie said,

“I'm still growing up, learning and making mistakes, just like any other teenager would - yet millions of people are watching and judging me. That's the part I don't know if I'll ever get used to.”

Kylie has talked about quitting social media in the past----but as her job requires her to stay current on her platforms she'll keep posting.

18 And She Had An Amazing MET Moment

Kylie Jenner wore a pinkish toned Versace dress with a super blonde bob wig courtesy of Donatella herself to the 2017 Metropolitan Museum Art Gala. And the lip kit guru kind of broke the rules at the event. There is a no camera rule but Kylie still managed to get an epic bathroom selfie with a few other celebs like Lily Aldridge, ASAP Rocky and sister Kendall, Diddy, Paris Jackson, Kim Kardashian, Brie Larson, Frank Ocean and a few others. Kylie even hinted that during this time of the event she was in a brand new relationship while filming her show, Life of Kylie ( Via E!).

"I've had more fun this month than I have in years… I really am happy."

We would later find out her new love was Travis Scott with whom she shares a daughter, Stormi, born in February 2018.

17 Kylie Was A Red Carpet Princess

Kylie is known for her edgier more revealing looks, but Kylie channeled her inner Disney princess at a 2016 Golden Globes after party. The look was much softer for the 18-year-old (at the time). The two-piece gown was embellished with metallic detailing and sheer panels, with just the right amount of skin to keep the look classy and paired the look with a sleek high bun. This look was a departure for the reality star who says fans don't really know the real her. “Nobody knows who I am except family and my close friends. But it is what it is. People have to be sensitive to - I hate using the word 'celebrities' - people in the spotlight. Because there's so much more than what you see on the cover of a magazine,” Kylie told Time. Kylie appears to be a private person despite her very famous upbringing.

16 Then She Was All Tasseled Up

By now you see that Kylie Jenner loves to wear Balmain on the red carpet. She decided to take the plunge and wear one of her most daring looks yet. It was a cross between a princess gown with a regal high neck and a curtain with tassels on the ends. And boy it was expensive.

The dress reportedly cost almost $25,000 according to Steal Her Style. She paired her light pink frock with clear lucite heels from Yeezy Season season 2 and a sleek blonde do'.

Kylie loves Balmain so much that she became the face of a collaboration between Balmain and Beats, for a collection of earbuds and headphones.”No matter what you're going through, when you put on a song that you love, and that you just connect with, it can change your whole mood and just lift you up. Even if it's just for a few minutes… I love that escape music gives us,” Kylie said on the Beats website ( via The Verge).

15 Her Pantsuit Was Red Carpet Ready

Kylie may be the baby of the family but her pantsuit showed a more serious side of the reality star---the businesswoman. Kylie has gone from bubbly teen to serious entrepreneur with a multimillion-dollar beauty company. Kylie had no idea when she sat down with Interview magazine that she would go on to rule the beauty world with her makeup brand, Kylie Cosmetics. “If I could do whatever I wanted, I would have a successful makeup line, and I would want to hopefully start more businesses, and just be, like, a businesswoman, and then, hopefully, I'll go off the map. When I'm, like, 30, I want to go off the map, have a family, and live in Malibu with a farm, and just raise my own chickens,” Kylie said to Interview Magazine. She's halfway there.

14 Kylie Is A Cut-Out Queen

Kylie wore a sleek and strategically revealing Bryan Hearns leather dress with a chain-link detail, and Tamara Mellon heels.

She attended the 2015 American Music Awards with sister, Kendall and despite not being a musician Kylie looked like a star on the red carpet.

But at the time Kylie had just split from Tyga for the hundredth time. "This is not the first time or the last that Kylie and Tyga will break up to makeup," a source told E!News. "Kylie and Tyga's age difference does add a bit of pressure to the relationship. Tyga is a father and has had more relationship experience than Kylie, she's still growing up." They did eventually split for good at the beginning of 2017 and she's moved on to rapper Travis Scott, they have been together for over a year now.

13 But Her Thigh High Purple Boots Were On Fire

Kylie has access to some of the trendiest fashion on the market like this pair of thigh-high purple boots from Balenciaga. She matched her boots with a white t-shirt and no pants. Kylie turns heads wherever she goes, but its all she knows.

“I've been famous for what feels like my whole life. I just want to know what it feels like not to be,” once told Complex about growing up in fame.

The reality star took out her Balenciaga boots to celebrate The PrettyLittleThing's Shape X Stassie Launch in LA. Stassie is actually, Anastasia Karanikolaou, one of Kylie's best friends and it just so happens that Travis Scott performed live at the event and this might be the beginning of Kylie and Travis' relationship. But at the time people still thought Kylie and Tyga were a thing.

12 And Then There's This Cool Mesh Ensemble

Kylie loves Balmain and she appears to like mesh/crochet too. The fashionista wore a fishnet bodysuit and high-waisted mesh skirt with a set of knee-high boots to grab dinner at Catch LA in 2017. And she looked amazing, but she admits that she feels the pressure to constantly stay relevant and available to fans!

“There's an image that I feel constantly pressured to keep up with. In order to stay relevant for the public, I have to be on Instagram and I have to be on Snapchat just keeping people entertained. And then there's who I really am around my friends… "

"… It's way easier for me to post on Snapchat or Instagram than it is to be out in public. I just feel like for so long I've been putting on this different persona to the world - I felt like I started to depend on social media, feeling the need to post all the time. I feel like I have to keep up this idea of who I am,” according to People.

11 And Her Denim Jacket And Mini Dress Were Too Cool

Kylie's been known to dress high-low (a combination of expensive and affordable fashion), but here she went fancy casual. In this look Kylie paired her bedazzled Yousef Al-Jasmi mini dress with a distressed denim jacket, taking the look from fancy to fashion-forward and fun. Kylie also pulled her hair into a high bun to show off her pretty face. Kylie's sister is only now taking a page out of her book when it comes to her fun fashion choices. Kylie personality remains a facade in front of fans despite her big social media following. “On Snapchat I show people what I think they want to see. That's not me. It's a projected image. A brand. I'm not a different person. I just don't show all of me,” she told Allure in an interview.

10 Kylie Was Totally A Rockstar At Fashion Week

Kylie usually toggles between glamorous and grungy in her everyday life, but the beauty guru was a total rock star when she sat front row at the at Prabal Gurung's spring/summer 2016 show.

The patterned pantsuit (courtesy of Prabal Gurung) was a departure from Kylie's other glammed up looks. But glam is a huge part of her business. Kylie has made a huge impact in the beauty business with the debut of her Lip Kits.

Even she was surprised her kits started selling out.“I've been so surprised. I didn't think my Lip Kit would be as huge as it is now - and the fact that people can't get it is crazy. But my goal wasn't to always have it sell out: I want girls to be able to get it as easily as possible. It's just that no matter how much we make, it sells out even faster every time,” she told Glamour.

9 She Channeled Her Inner Barbie

Kylie channeled her inner Barbie when she stepped out in a bright powdery blue mini dress with a fringe bottom, with strappy sandals and super high blonde ponytail. She worked the look during Fashion Week in September 2016, in NYC. She had been wearing her hair in a short blonde bob but opted to add long extensions to the look. Kylie, still just a teen at the time, wore this stylish dress out to dinner with then-boyfriend Tyga. She wore a toned-down makeup look with a simple brown smokey eye and nude lipstick (one of her signature looks). This was just a few months before the couple officially called it quits in early 2017. So much has changed in a little over a year, Kylie is now a mom to baby Stormi with rapper boyfriend, Travis Scott.

8 Kylie Looks Just Like Joan Jett

We've seen Kylie Jenner look like a rock star before, but for the 2017 Alexander Wang runway show, she actually looked like singer Joan Jett. Kylie, who of course sat front row debuted one of her most dramatic looks---she left her long extensions at home and instead went with a with a wet-looking shoulder length shaggy hairstyle and brow-skimming bangs in her brunette shade.

It was probably a wig, but we sure did a double take on Kylie's homage to Joan. Kylie's hair perfectly matched her black bodysuit and oversized plaid jacket for the updated 70's look.

The look was perfected by Kylie's longtime stylist (and wig/extension) guru, Tokyo. Some fans on social media were not fans of the look, but she's a trendsetter. Some people are might not like the look.

7 She Made Denim On Denim On Denim Look Effortless

It can be hard to pull off the denim on denim look (or the Canadian tuxedo), but Kylie makes it work with ease. She wore distressed denim jeans with an oversized denim jacket and a denim belt to tie the entire look together and give her a cinched in waist. The look was a slightly more affordable than her other high profile fashion choices---kind of. According to Steal Her Style Kylie was wearing--a Levi's The Trucker Jacket which went for $89.50 and AGoldE Sophie Crop Jeans at about $158.00. But here's where she went over the top----she paired her look with super expensive earrings----Harry Kotlar Classico 18K White Gold Earrings ($50,570.00) and Yeezy Season 3 PVC Ankle Boots at almost $700. Talk about a High Low outfit choice!

6 Making Plain White Shirts High-Fashion

It's unclear how she does it but Kylie knows how to make plain white T-shirts into fashionable moments.

Yes, she is not wearing pants and of course, there are a few amazing accessories like her green thigh high boots and matching belt, but Kylie's fashion magic just works, even with just a plain t-shirt.

Kylie and sister Kendall were slapped with a lawsuit over a t-shirt, with the face of the late rapper Tupac Shakur. The ladies were handed a lawsuit by the photographer Michael Miller (who owns the image) after the photo was emblazoned on a T-shirt for one of their Kendall + Kylie label shirts. The lawsuit has since been dropped, at the request of both parties, but it's unclear if there was a financial settlement according to Mercury News.

5 And Her Cutouts Were Crazy

We are starting to think that Kylie Jenner only wears Balmain on the red carpet. Another ensemble that wows on the red carpet was the purple cutout outfit for the 2017 Marie Claire Image Maker Awards this week. The interesting dress appears to be two pieces but in fact, it's just one. The top portion of the dress looks like a crop top, but if you look closely there is a skin tone mesh panel that connects to the bottom of the dress. Then there are another set of clear panels running down the sides of her legs showing off her great gams. The dress looked like a combination of a cheerleader's pom-poms and shredded paper but she knows how to make a statement. Kourtney Kardashian wore a similar dress to the 2016 Angel Ball back in November.

4 She Brought Crop Sweaters To A Whole New Level

Only Kylie Jenner can get away with wearing a sweater so cropped that it can barely be categorized as an actual sweater.

The Harley Davidson's logo is almost torn all the way off in this exaggerated look that caused quite a Twitter storm online where fans just couldn't get over the non-top Kylie was wearing with a skin-colored tank top---some even called it a "sweatshirt necklace".

The top was a Sami Miro design and only really covered her arms and not much else, according to Teen Vogue. But set this crop top aside and let's talk about the reality stars affinity for purses. According to ThisIsInsider, Kylie has amassed quite a handbag collection. After she recently showed off her extensive collection that the DailyMaild guessed that it was worth about $1 million, while People said it was more like $250,000. Nonetheless, Kylie's collection is highly covetable!

3 And She Looked So NYC In This All Black Ensemble

Kylie looked super cool wearing her all ensemble.She's giving major NYC meets the Matrix vibes with her long black trench coat, short black dress, and boots. She also added black sunglasses and purse. Kylie left her California girl fashion behind with this outfit which included, a Haider Ackermann wool coat ($2,179), a vintage dress, and Tom Ford lace-up thigh highs ($1,225 ) according to The Fashion Bomb Daily. Can you believe that Kylie was only headed to lunch at The Smile Cafe in SoHo with Kendall when she was seen with her all-black outfit? So over the top. Kylie has been known to overshadow her sister Kendall's style despite her supermodel status and extensive access to designer duds. Kendall and Kylie still have a fashion line together despite their very different styles.

2 Kylie Made Orange Look High Fashion

Kylie's been making waves for years, but when she wore an orange mini dress to the 2014 MuchMusic Video Awards in Toronto everyone took notice. Kylie was just 16 years old when she wore this Nicolas Jebran orange beaded cocktail dress with sheer panels on the awards red carpet. And the teen also hosted the awards with her sister Kendall.

According to HollywoodLife, the ladies changed their look three times during the show. This was before Kylie's notoriety took off (pre-lips). It was towards the beginning of Kylie's fashion evolution from little Kardashian sister to budding social influencer.

This was before Kylie became the social media phenomenon she is today. Before her million dollar beauty brand, her relationship with Tyga, before becoming a mom at just 20. She's lived more than most people twice her age.

1 But All Her Hairstyles Are Her Real Statement Pieces

Kylie has a fun fashion sense, she likes to mix high and low items, but she can still break out the sweatpants without looking sloppy, but when you think of Kylie you think of her hair. She has been changing her hair for years even before she had her famous lips. All she wants to do is inspire her fans.“And I do feel like I inspire them - because I'm always changing up my look and experimenting. So, one week I'll be really glam and girlie, and the next, a punk with blue hair. I see a lot of girls following my trends and because they're experimenting, becoming more comfortable in their own skin.” We think she's even inspired her big sisters to try fashion outside the box. Kylie's most famous sister Kim K. used to be really safe with her fashion choices, now she likes to take a risk and try different things.

REFERENCES: Interview Magazine, Cosmopolitan, People, E!, Time, Steal Her Style, The Verge, Interview, E!, Complex, People, Allure, Glamour, Steal Her Style, Mercury News, Teen Vogue, This Is Insider, Fashion Bomb Daily, HollywoodLife, Glamour