25 Times Kylie Jenner's Outfits Made Us Say Wow - But Not Always In A Good Way

Instagram / The Talko

The youngest Kardashian-Jenner sister is arguably the most popular of them all.

She'll literally do anything to entertain her fans. Whether it be showcasing the ups and down of her life on her new show Life of Kylie, appearing on Keeping Up with the Kardashians, or showcasing her style on social media platforms.

Kylie always finds a way to blow us away, but sometimes we're not cheering for her, we're questioning her.

Check out some of her fashion disasters and let us know what you think...

1. Bigfoot Called He Wants His Jacket Back

I'm a little bothered by the fact that she's wearing only one shoe, but I can live with that.

What I can't live with is that massive down jacket that makes her look ridiculous.

Imagine lugging that around a mall.

2. "Bend And Snap!"

I'd have to be drunk to leave the house looking like this.

There's a line between flattering and just plain inappropriate. Kylie has definitely crossed that line on way too many occasions.

3. My Mom's Drapery Tassels

Apparently this dress is worth a whopping $25,000! If this is considered fashion, I have no idea what fashion is.

This is an outfit I'd probably find in the Halloween section of Goodwill, not in high fashion boutiques. I'm just saying...

4. Croch-Nay

This Yeezy bodysuit and sheer blue crochet skirt is interesting, to say the least.

I think I have more fashion sense than one of the most famous women in the world.

5. "You Should've Seen The Other Guy"

This Harley Davidson sweater is so cropped that you would think she got into a fight with a wild cat.

The kitty also scratched her legs while trying to tear at her top. Surprisingly her beige tank top was left unscathed.

I made up that story, but it could be true.

6. When You Forget To Look In The Mirror

You know those times when you leave your house and only put your full-body pantyhose on, forgetting your shirt and pants?

Oh, you don't? Because I don't either.

7. A Doll's Dress

This plain white dress is actually cute. The only problem here is that it has a horror movie vibe that creeps me out.

8. A Little Bit Mismatched?

I love every piece of this outfit, but not when it's worn together.

I'm not a fashion police, but right now I need to be.

That silver necklace would look nice on a plain dress, and the choker would look nice on its own.

The sunglasses and top look good together, but not with that fanny pack. And that headband should be reserved for Coachella only.

9. "Wo-Man's Not Hot"

It looks like Kylie's wearing a one-piece that's made of velvet, which I assume would be very warm.

On top of the thick velvet, she's wearing a thin camo jacket, and on top of that she's wearing a thick camo jacket.

If it's that cold, she should be wearing a hat and a scarf.

10. Silver Brush

Kylie definitely knows how to make a statement, which is probably why she's referred to as a fashionista.

I want to like this dress, because I feel like it has potential, but there's something inside me screaming that I shouldn't. I've got to go with my gut feeling on this one.

11. Fruit To Go

Kylie has become a walking advertisement for those delicious thin strips of Fruit to Go Strawberry that we all love so much.

She did one for the team, thank you.

12. Grandma's Undergarments

In the early 1900s, this would classify as underwear. Women would wear these under their big puffy dresses because that's just the way things were!

Times surely have changed.

13. Needs More Stitching

Wearing revealing clothing is Kylie's forte, so I'm sure this ensemble is something she's extremely proud of.

14. DIY Gone Wrong

I like how her boots and dress match, but I'm not crazy about her obsession with mesh-like clothing and crochet.

She says she feels a lot of pressure from fans to "keep this idea of who [she] is," but apparently that's all a facade.

Kylie, if you don't like mesh we won't judge you. We don't like it either!

15. Wannabe Mermaid

Kylie wore this Versace dress at the 2017 Metropolitan Museum Art Gala thinking she looked like a superstar.

Okay, she did, but how are we supposed to hold back from commenting on just how ridiculous this dress looks on her.

The trinkets are tacky and the dress is see-through, leaving no room for the imagination.  

16. When Your Niece Designs Your Clothes

This dress is actually two pieces, and not one. I know, surprising.

This dress also looks like it used to look good, until a kid went ham with a pair of scissors.

I think the only solution is for the Kardashian-Jenners to lock up North West's scissors. It's honestly for the better.

I really hope Kylie's daughter, Stormi, doesn't get any ideas when she gets older.

17. Dumpster Leftovers

Her booty shorts are so torn apart that at this point they need to be thrown out.

But you've got to give credit where credit is due. You've got to be extremely confident to leave your house looking like this.

18. That Belt Tho...

The first rule of fashion that my mother passed down to me was this: Don't match denim with denim. It's tacky, and people will point out your wardrobe malfunction.

Not only is she wearing jeans with an oversized denim jacket, she's wearing a belt that's longer than Rapunzel's hair.

19. Is She Fo' Real?

It looks like Kylie just stepped out of her front door, so I hope she realized how ridiculous this looks and stepped right back in.

20. Where Should I Start...

Did Shaquille O'Neal lend his hand-me-down collar shirt to Kylie?

21. Too Much Money Maker

Remember that line between flattering and just plain inappropriate that I was talking about? Well, she crossed that again.

22. Grab And Go

The best part about being a celebrity is that you can wear some outrageous accessories and no one's going to make fun of you for it.

I'm not going to lie, I actually like what Kylie is pulling off here. It's a good kind of different.

23. Undecided

Another reason why being a celebrity is great: Your clothes can look like it's been torn apart by a German Shepherd and no one's going to question how much money you've got in your bank account.


Kylie didn't write a caption for this Instagram post, which makes me worried that she's wearing a poor animal's fur on her body.

I'm not the only one who thought this way!

"Is that fur? How you can follow someone who is wearing fur!!" one Instagram user commented.

"You wear dead animals. It's not beautiful or fashion, it's violence and cruel and animal abuse...STOP!!!!" wrote another.

Apparently this isn't the first time the reality TV star has been in hot water for wearing fur. She's been targeted by anti-fur protesters on more than one occasion.

25. Kendall + Kylie

Despite all these clothing disasters, Kylie's making it big in the world of fashion.

She and her sister, Kendall, introduced their first ever fashion line called Kendall + Kylie and it's actually not all that bad.

It's different, and sometimes different is what we need.

But I must say, Kendall's outfit looks so much better than Kylie's. I wonder if Kylie designed that cut-up dress all by herself.

Which outfit shocked you the most?

Moojan has been a writer at Shared for a year. When she's not on the lookout for viral content, she's looking at cute animal photos. Reach her at moojan@shared.com.