29 Times Kylie Jenner Proved She Is The Most Stylish Kardashian, From Edgy Rock Tees To Body Con Dresses

Being the youngest sibling can suck it at times, like when you get hand-me-downs instead of brand new back to school clothes. It can also be a situation that slays, since moms always favor their babies, often letting them get away with murder since they've been there and done that. Being the youngest sibling and youngest female in a house full of fashionable glamazons who are filmed for a reality show watched by millions is one of those sink or swim situations — and Kylie Jenner is doing a flawless backstroke. Kylie Jenner's certainly seen as the edgiest Kardashian, what with her multi-colored hair and all, but what about the most stylish Kardashian? Some might say Kendall takes that title, but I'm definitely Team Kylie. Hear me out.

While her big sis Kendall is the toast of the modeling world right now, Kylie Jenner continues to nab plenty of attention for her lips and her sass. Not gonna lie... next to Scott Disick, who is fully entertaining in his obnoxiousness, Kylie Jenner is my favorite satellite Kardashian, thanks to her irreverence, her insanely on-point sense of style, and her ability to start a trend, rather than chase one.

Whether she is all dolled up or glamsual, Kylie has this innate sense of what works for her sartorially, mixed with a little do-whatever-she-feels-like. Here are 29 times that Kylie proved she is the most stylish Kardsahian. Sorry, Kim, Kendall, Khloe, Kourtney, and Kris.

Let Her Rip

Jenner knows how to navigate a pair of ripped jeans better than any of her sisters. She treats them like a cool cornerstone of her ensemble, and wears them often, not as an afterthought.

Image: @kyliejenner/Instagram


Jenner has shown a preference for black clothes, to go with her hair and lips, but this midriff-baring outfit was so simple. She gave it an edge thanks to those heels.

Image: @kyliejenner/Instagram

She Wears Short Shorts

Jenner often plays with volume, like she did here with short shorts, an oversized top (or jacket), and those boots. Don’t worry. We’ll talk about those made-for-walkin’ boots again in a sec…

Image: @kyliejenner/Instagram

Moto Boots

While Jenner isn’t afraid to rock dominatrix, over-the-knee boots, she also swaps things out with chunky moto boots from time to time. They added a masculine touch to her mini skirt and crop top.

Image: @kyliejenner/Instagram

Boots 'n' Bag

The destroyed denim; the pointy, Wicked Witch of the West boots; and the structured Balenciaga bag, complete with its furry charm, were truly and madly Kylie.

Image: @kyliejenner/Instagram

Recycle + Repeat

Jenner isn’t afraid to be seen in the same pair of ripped jeans twice. She totally styled them differently, this time with tan work boots.

Image: @kyliejenner/Instagram

Earning Her Stripes

I am used to largely monochromatic Kylie looks, so when she goes with stripes, it’s a bit of a surprise. But she rocked this look. That skull ring could knock a few teeth out, too.

Image: @kyliejenner/Instagram

She Can Be Classic, Too

Kylie’s nails are often long, sharpened to a dagger-like point, and lacquered in black. But she can also go classic, like she did here, with a rich, ruby red shade on her digits.

Image: @kyliejenner/Instagram

Those Boots

Whoa, she likely had to be sewn into those boots. Those are some s–t kickers, Kylie!

Image: @kyliejenner/Instagram

Belly Baring

Kylie pulls off the sweatpants and crop top look better than anyone.

Image: @kyliejenner/Instagram


She isn’t afraid to siphon style ideas from her sisters — in this case, the voluptuous Kim. She kopied her big sister’s kleavage and hair, but still looked Kylie-fied.

Image: @kyliejenner/Instagram

Rock Chick

Kylie’s effortless use of a leather motorcycle jacket to punch up her white dress was flawless. Kim didn’t even rock a moto jacket when she and Kanye hopped on a bike for the “Bound 2” video.

Image: @kyliejenner/Instagram

She Even Wears Converse!

Kylie isn’t in heels 24/7, even if they are her shoe of choice. She has the guts to go casual in her Converse high-tops once in a while.

Image: @kyliejenner/Instagram

Shady Lady

Those cat-eyed glasses are amazing. While everyone else rocks big, black sunnies, Kylie did so with an elongated twist.

Image: @kyliejenner/Instagram

Family First

The recent Cosmo cover girl showed support for her brother-in-Yeezy by wearing one of his tour shirts.

Image: @kyliejenner/Instagram

Is That Her Closet?

Suddenly, I am semi-green with envy.

Image: @kyliejenner/Instagram

Accessories Queen

Jenner’s got a knack for accessorizing, pairing multi-strands of chains with those aviators. She looks like she is about to head out on a road trip.

Image: @kyliejenner/Instagram


She layers her necklaces and it looks so effortless, like she grabbed a handful off her vanity, threw them around her neck, and hit the road without thinking twice.

Image: @kyliejenner/Instagram

The Simple Sister

Now this is a Kardashian showing off simple, natural beauty. She took a basic, a darker wash denim jacket, and gave it a boost with the black aviators and chocolate x black ombre locks.

Image: @kyliejenner/Instagram


That coat, with its squared off shoulders and military cut, elevates her entire look. Kim is known for trying unusual cuts, but on a young style brat like Kylie, it demonstrates a fashion wiseness beyond her years.

Image: @kyliejenner/Instagram


Kylie Jenner’s accessory style isn’t basic. She tends to wear multiple pieces at the same time. In this case, she rocked many rings. On her sisters or her mom, it would’ve been overkill.

Image: @kyliejenner/Instagram

T-Shirt Girl

Kylie Jenner is often seen wearing concert tees. While on anyone else in her family, it’d seem like putz-around-the-house wear, she incorporates them into her outfit as an integral piece. While Kim and Khloe prefer tracksuits, Kylie rocks out when casual.

Image: @kyliejenner/Instagram

Throwing Shade

Kylie Jenner’s sunglasses game is usually on point. These white frames with blue lenses are crazy unique.

Image: @kyliejenner/Instagram

A Leg Up


Jenner’s wine-hued satin dress with a major slit proved that she takes red carpet risks.

Mirror, Mirror on the Wall, Who's the Edgiest of Them All?

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Kendall looks adorbs and all, but it’s Kyle’s sweet peplum top and shorts that blows me away. She stands out for all the right reasons.

Robe Done Right

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Jenner’s got great legs and she isn’t afraid to show them off when wearing a robe-like gown on the red carpet. This is Kylie’s take on PJ chic, and the simple black made it way more wearable than Kim's Grammys robe (sorry, Kim).

A Beacon in White

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Kim wore a similar white outfit for her birthday in Las Vegas one year and she was busting out, showing off her assets. Kylie’s outfit is similar and subdued and she instead opted to let her hair be the main feature.

Dark Days

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Jenner donned all black and not even in glamsual fashion. This was straight up masculine and it’s not something any of her big sisters would be caught dead in. Yet another reason to love her, for daring to reinvent Kardashian fashion.

Body Con


The body con look is certainly a Kardashian hallmark, but Kylie veered a bit to the left with her take on the trend by pairing her clingy, midi-length dress with ankle booties. Strappy heels would have been too, too easy.