Street Style Vs Red Carpet: 20 Photos Proving Kylie Jenner Is Always Best Dressed

It is impossible to underestimate how much the world seems to care about Kylie Jenner. After leaving tabloids to speculate for months that she was about to give birth, the emergence of her daughter, perhaps aptly named Stormi, has created another frenzy of media attention.

If the trend of past high-profile celebrity pregnancies is anything to go off of, it's inevitable that the next level of attention will be focused on how her body will rebound from the pregnancy. Kylie definitely has a high bar to compete against when you factor in just how amazing she looked before she fell off the radar.

With over 100 million followers on Instagram, Kylie is a natural target for the paparazzi who have managed to catch her in some seriously eye-catching outfits over the years. And when you consider she has admitted to taking hundreds of selfies a day, you may understand why the world knows so much about how she looks on a daily basis.

But as stunning as she looks when she doesn't think anyone is watching, Kylie may leave you even more stunned in the other half of our list where she was planning to be photographed.

Whether on the street, at a red carpet event or in a photo shoot, it's going to be abundantly clear that wherever she goes, she looks good!

20 Red Carpet - Explaining The Bond Of Her Sisters

One of the most important bonds that you can have in your life is that of your family. And while people may like to sass the Kardashian and Jenner clan, it is very clear that they are a tight-knit group. Kylie has discussed the value of having sisters, as well as the individual "perks" that came with each sister,

"Having sisters is the best. I have a different relationship with each of them. I go to Kim for fashion advice, Khloe is always boy and family advice, and Kourtney is like another mother to me."

She can also often be seen on the red carpet with sister, Kendall, close by. Given Kendall's tremendous success in the modeling world, you can guess she'd also be a great source for fashion advice!

19 Street Style - Stating How Often She Changes Her Style

When talking about her overall sense of style and what her overall goal is, Kylie has admitted,

"I change my style maybe every month. I'm, like, punk one month, ghetto fab the next, classy the next. I'm just young and finding out who I am."

One of the main elements in the life of Kylie Jenner is trying to decide what type of style she wants to introduce into the world next. Because let's be real here, it is only going to be a matter of time before what Kylie is wearing before it becomes a popular trend seen by other young celebrities.

18 Red Carpet - Showing Off Her Designed Sunglasses

When you first look at the above photo, you may not first get that she's actually putting on an advertisement for the glasses.

Kylie is one of the biggest faces of the sunglasses company, Quay Australia (bonus points if you can guess where they're located). Jenner jumped at the opportunity to work with the company as she not only got to model the glasses but also was the designer of the styles.

"I love sunglasses that make a statement. They are such an important accessory and I love switching them out to go with my outfits," said Kylie to ELLE.com

17 Street Style - Beach Paparazzi

One of the most important aspects of being a successful celebrity, especially in the way that the Kardashian/Jenner clan is, is to make sure you are constantly putting yourself in the public spotlight. It is possible that always needing to do this, and in the process, being at the mercy of photographers, led to Kylie once saying,

“I feel like I’ve had anxiety for too long. I feel too much, I care too much, I read too much. Some people are born for this life and some people aren’t. I just know I’m not supposed to be famous.”

16 Street Style - Downplaying The Role Of Surgery

There is no question that as long as Kylie Jenner continues to make appearances in the public eye, that people are going to be questioning whether or not she has had artificial work done to enhance some of her more eye-catching features. But when talking about the state of her body and her overall attitude towards fitness, Kylie revealed,

"I swear there are things you can do to work on problem areas without having to think about surgery."

We're sure haters of Kylie will probably just assume she was lying with that quote though!

15 Red Carpet - Looking Like A Barbie Doll And Discussing Enhancements

You wouldn't be the only person if your first impression of the above photo was that Kylie looked like a Barbie doll. But while Kylie has denied putting any plastic into her figure at this point in her career, she has come out in the past and stated that it may not always be that way,

“I’ve thought about it, but I’m like, why ruin it? I’m not against it, but right now, it’s a no from me," said Kylie in 2016 to InStyle.

The photo featured in our above entry was taken for Flaunt magazine and ended up being published in their May 2017 edition.

14 Street Style - Explaining What Her Favorite Feature Is

There is no shortage of features on Kylie Jenner that you may not be able to take your eyes off with our next photo. But if you sat Kylie down and quizzed her about what feature on her body she loves accentuating the most, you may be surprised at the answer.

"Lips are kind of like my thing, and I've always been obsessed with lipstick and lip liner. I just always went to lip liner to overline my lips, and I feel like I was really known for that. I can't walk out of my house without my lipstick!" said Kylie. No wonder lip products are such a huge part of her fashion line!

13 Red Carpet - Revealing The Importance Of Her Stylist

Kylie Jenner knows that there is a lot of pressure on her to always be looking her best, especially when she attends red carpet events. When discussing how she handles this to People magazine, Kylie stated,

"It is a little intimidating to look good all the time, but I just try to make outfits and meet with my stylist. We will just talk and collaborate. We will throw ideas around and talk about the stuff that we like. So it’s really cool."

There may not be a more important employee that Kylie hires than her stylist! Except for perhaps whoever her new nanny is.

12 Street Style - Her 18th Birthday Came With a Lucrative Film Offer

In America, turning 18 isn't a super huge deal - especially in comparison to when you turn 21. But that didn't stop Kylie Jenner from pulling out all the stops with a stunning silver dress for her 18th birthday back in 2016.

One of the more significant elements that, does, however, come with turning 18 is the ability to perform in the...other type...of film industry. While she denied the requests for obvious reasons, reports surfaced shortly after she became the legal age that Kylie was offered upwards of $10 million to film her bedroom activities. We're sure she's glad she doesn't have to have that future conversation with her kids. She can, however, talk to them about Aunt Kim's video.

11 Red Carpet - Shining In Silver At Golden Globes

One of the most star-studded events of the year for celebrities is the Golden Globes. Kylie may not have experience in the traditional movie or film world, but that definitely isn't going to stop her from earning an invite to the awards show.

She shimmered in silver back in 2017, and while the dress is revealing, she managed to avoid a wardrobe malfunction. We're sure that if she chooses to make an appearance at next year awards show that everyone will be talking about how her body has bounced back (or failed to) from her pregnancy. No pressure Kylie.

10 Street Style - Stating She Knows Her Angles For Showing Off Backdoor

While Kylie Jenner is no stranger to flaunting some of her most prominent assets on a regular basis, what you see when you stare straight at her isn't the only area that she has had to deflect rumors has been enhanced.

When talking about her backdoor, Jenner defended herself saying,

"I know my angles.”

Kylie is also surely not going to upload a photo if she doesn't look amazing in it, which also increases the overall positive reaction her body should receive.

9 Red Carpet - Explaining The Role Of Makeup Before Bed

You can understand that getting ready to appear on a red carpet may be an incredibly time-consuming process, even with a team of professionals to help you along the way. But one thing you may not think about is how much time may be spent after the event getting ready for bed!

While some women may elect to fall asleep with their makeup still in-tact, Kylie makes sure not to.

"I can't sleep in my makeup ... I have a full ritual I try to do every night, but if I'm not feeling it, I'll usually take a wet paper towel and some makeup remover and just wipe my face really quick."

8 Street Style - Explaining She Doesn't Wear A Lot Of Makeup In Everyday Life

Kylie Jenner is often going to be photographed while running errands around town. And while she isn't going makeup-free in the above photo, Kylie assured an interviewer that the role of makeup in her life isn't as heavy as you may anticipate.

"If I'm going to see people, I won't wear heavy makeup. It's not attractive on me. When you see those pictures on my Instagram, they are usually for when I'm doing a photo shoot or an interview."

We're sure with the birth of her new child that Kylie will find herself doing a lot fewer photo shoots and interviews!

7 Red Carpet - Modelling Her Kendall + Kylie Line

Love or hate the Kardashian/Jenner clan, it's hard to deny that they aren't tremendous at turning their image into marketing opportunities. Kylie and Kendall teamed up together for their own fashion line. Though we can't promise that if you buy an outfit from them that you're going to look as amazing as the two girls when they model it.

When talking about the evolution of the brand, Kylie revealed,

"We have learned what the customer wants and what she gravitates towards through trial and error. We love to push the envelope with adding statement and novelty styles that in the past we would have shied away from and seeing how our customer has loved those items has been amazing."

6 Street Style - Pregnancy

Kylie Jenner didn't come out and confirm her pregnancy until she had finally given birth to her baby girl, Stormi. But that doesn't mean she didn't take pictures of her journey, she just didn't share them at first. Now that they're out there, many people are praising Kylie for managing to continue remaining stylish while rocking a bump.

We're sure having Kim, Kourtney and Khloe (to start with!) to help ask for advice also helped make a big difference in Kylie having a smooth and comfortable pregnancy.

5 Red Carpet - Admitting Where She Splurges Money

When you look at Kylie Jenner all done up for the red carpet in the above entry, you may get the idea that she spends a significant amount of her money to keep looking that way. But when Kylie was talking about where she manages to splurge her money the most, she admitted,

"I like to know exactly what's going on [with my finances] and I'm actually quite careful with what I spend. We all are as a family … And I don’t really like splurging — unless it's on cars. That's the thing I spend the most on."

Which means we're also sure she made sure to get a car with a high safety rating for the baby!

4 Street Style - Claiming She's Flashier On Social Media

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When discussing the role of social media in her life, at least at one time, Kylie exclaimed,

"I'm way flashier on Instagram and Snapchat because I feel like that's what people want to see, and that's 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."

While there are many perks to being a celebrity, one of the main drags may come with the fact that you are constantly required to be promoting a certain image of yourself or helping to promote and sell other brands. Kylie Jenner is one of the biggest celebrities in utilizing Instagram and other forms of social media to keep connected with her fans.

3 Red Carpet - Expressing Her Preference For Black Hair

There are many celebrities in Hollywood who are known for being able to pull off different types of hair colors. But if you asked Kylie Jenner what her preference for her hair is, she'd be emphatic that it needs to look like it does in the photo we've selected for you above.

"I can't have brown hair for some reason. I don't think it goes with my skin tone. The second I see it turn brown in the sun, I dye it black - the blacker the better," said Kylie.

While she'd probably still turn heads as a brunette, nobody should fault her for having a preference.

2 Street Style - Showing Off Her Leg Injury

Kylie Jenner may look flawless in some of the photos on our list, but everyone has their imperfections and in many cases, scars. For Kylie, one of her most noticeable ones can be found on her leg. Naturally, it has become the topic of conversation. In a past interview, Kylie discussed the story behind her mark,

“When I was about five, my sister and I were playing hide-and-seek, and I hid inside this really tall-enclosed gate. After a while when my sister didn’t find me I had to climb up on this sharp pole sticking out from the gate. I slipped and the pole went into my leg. I tried pulling away to get the pole out but it just tore through my whole leg,”

That's what she gets for being really good at hide n' seek!

1 Red Carpet - Tyga's Weird Bedroom Request

Kylie's recent birth of a daughter was with her long-term boyfriend, Travis Scott. But that's not the only boy that Kylie has brought home to bed. One of her more serious relationships was one with musician, Tyga, that lasted from 2014-2017. While Tyga and Kylie had too many tabloid stories to count, one of the more eye-catching included Tyga's alleged preference for what she would wear behind closed doors,

“Tyga only likes [being intimate] with Kylie when she is completely made up, that is what turns him on when she has all of her makeup on. He considers it the only option when they have s*x. No makeup, no [intimacy]."

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