Countless Times The Kardashians Made Hilarious Fashion Mistakes

1 The Couch Dress

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Who could forget when a very pregnant Kim Kardashian wore this Givenchy Roses Dress to the 2013 Met Gala? This gown is just wrong on so many levels.

Unless, of course, Kimmy’s goal was to look like a couch. If so, she accomplished just that. It doesn’t look like a very comfortable couch, though.

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2 Leopard Disaster

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Khloe Kardashian posted a matchy-matchy pic on Instagram with her daughter, True. She wrote the caption, “A leopard and her cub.”

While True looks adorable in a leopard print headscarf, Khloe looks like something the cat dragged in. This get-up is just too wild for us!

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3 The Green Machine

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kourtney Kardashian assaulted our eyes when she wore a mint green Salvatore Ferragamo set in May 2021. She donned the outfit to promote an installment of the Poosh brand’s “Shop Drop” series.

We think she should’ve shopped around and dropped that horrible set. The matching ruched bloused and textured flare-leg pants are a massive fashion fail.

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4 Grandma’s Curtains

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian wore a form-fitting velvet gown that left little to the imagination for a night at the opera in New York City in December 2019. How is this look sexy?

She must have seen this hanging in the window and had to have it because she looks like she’s wearing her grandmother’s drapes. The lace-up heels might as well be curtain cords.

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5 Dominant Woman

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim has a thing for full body outfits, but also for leather clothes. When she combines the two, it can make for some pretty questionable results!

On September 12, Kim posted a picture on her Instagram, walking in front of her black Cadillac Escalade SUV wearing this all-leather look from Balenciaga. She was going to the Mark New York Fashion Week, but we definitely feel like she’s ready for a different kind of special night!

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6 Cage Dress

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian committed a fashion crime in March 2015 at Paris Fashion Week. She squeezed herself into a strange cut-out dress with a long overcoat and black boots.

Does anybody else think it looks like she’s stuck in a cage? I mean, she probably should go to jail for this getup.

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7 Haute Mess

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Who could forget when Kylie Jenner showed up at the 2019 Grammys looking like a stick of cotton candy gone wrong in an oversized pink suit? Apparently, the fashion police loved this look on her.

The Balmain Haute couture suit came fresh off the runway. It just looks like a Haute mess to us!

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8 Sequin Nightmare

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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The paparazzi snapped a pic of Khloe Kardashian leaving a studio in Calabasas in January 2017. She wore blue sequined trousers and a matching jacket on top of fuzzy black flip-flops.

We’re getting a slight Smurf vibe from this one. She looks like Smurfette after a rough night at the club.

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9 Mesh Dress

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kourtney Kardashian left little to the imagination when she stepped out in a see-through dress while vacationing in Cabo San Lucas, Mexico in August 2018. She wore a nude bodysuit underneath that hugged her curves.

I see London; I see France; I see Kourtney’s underpants!

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10 Distressed Denim

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian tried to bring back the acid-washed jeans trend while out on a lunch date with a friend in Bel Air in June 2017. She topped the outfit off with a black hoodie.

We feel totally torn about this one. Her jeans actually look more stressed than distressed. At this point, can we really consider that she wears jeans?

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11 Totally Ripped

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kylie Jenner lost half of her sweatshirt. Photographers spotted her in Los Angeles leaving North West’s 4th birthday party at Ruby’s Diner in June 2017.

From the homemade crop top to the distressed jeans, this entire ensemble is just wrong. Isn’t she rich enough to buy an entire sweatshirt?

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12 Torture Devices

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Poor Kim Kardashian abused her feet while lunching in Los Angeles. She was pregnant with North West in May 2013 when she stuffed her swollen tootsies into those shoes.

We get that she’d do anything for fashion, but this looks painful. It seems like her big toes are screaming out in pain. One wonders how long it took her to stop feeling her feet.

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13 Trash Bag

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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You’d think that Kendall Jenner would glam up for a visit to the Chanel showroom in Paris, France. The paparazzi snapped her wearing this strange frock in April 2016 and we have questions.

Is she aware that she looks like she’s wearing a trash bag? Is homeless chic a thing? With all the money she has, she can certainly do better than that!

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14 Fishnet Bodysuit

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Khloe Kardashian stepped out in a nude fishnet bodysuit in Las Vegas in March 2019. This outfit is not the best look on her. It wouldn’t be on anyone, mind you.

It just seems tasteless. Of course, if she was trying to look like a call girl, then she totally nailed it. Maybe she would catch fish if she jumped into the sea!

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15 Bad Babydoll Dress

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian slapped on a textured babydoll dress while in New York City in March 2013. This is another maternity look she wore while pregnant with North West.

The body line of this dress isn’t working for us. That skirt is just absurd. Kim really made some questionable clothing choices when she was pregnant!

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16 My Scary Valentine

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kourtney Kardashian posted this pic on Instagram along with the caption, “Bonjour, oh and your Valentine’s Day gift guide is up on @poosh ❤️”. What is happening in this photograph?

From the vintage hat to that terrible dress, this outfit has us scratching our heads. What are these strange patterns? It looks like a child’s painting!

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17 Matchy Matchy

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Let’s travel back in time to the 2008 Victorias Secret Fashion show in Miami, Florida. Kim and Kourtney Kardashian walked the pink carpet in these horrid coordinated dresses.

That means both of them had to approve this look. Somebody needed to fire their stylist. One thing is certain, such a matching look is not likely to happen again!

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18 Tassel Trainwreck

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kylie Jenner posted this pic of her in an appalling tassel dress on Instagram in September 2016. She saw this one in the window and just had to have it.

No kidding. It looks like she made a dress out of the nearest drapes. We can’t believe she paid for this dress. And probably a considerable amount of money at that!

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19 Dementor Style

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Every year, the famous MET gala is held, where celebrities parade around in the most creative outfits. For the 2021 edition, Kim once again made people talk with her style—it’s becoming a habit!—which was a reflection of quantum mechanics.

Indeed, this outfit signed Balenciaga and compared by many to the dementors in the Harry Potter saga was in fact the beauty equivalent of Schrödinger’s paradox.

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20 Sunday Best

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Kim Kardashian crammed herself into a latex suit while in Paris for Kanye’s Sunday service in March 2020. It’s a miracle she could sit for the sermon in that thing.

This outfit is perfect for church. Nothing says “I love the Lord” more than a tight latex bodysuit. Still, ironically, isn’t that a bit too revealing of her body curves for church?

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21 Plastic Pumps

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kourtney Kardashian jumped on the clear shoe trend while out and about in Los Angeles, California. Let’s zoom in on these practical plastic shoes.

Um… her toes were sweating so much that her shoes fogged up. Is this even hygienic? This is a very bad choice of shoe. Let’s bet she never wore them again.

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22 All Tied Up

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Kim Kardashian laced herself into some strange thigh-high boots while meeting Scott Disick for lunch in Los Angeles in May 2016. Those laces are working overtime.

This is a totally appropriate look to meet your sister’s ex-boyfriend for lunch. Not racy at all. We can only imagine how long it takes to tie them up and we are discouraged!

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23 A Denim Don’t

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Kylie Jenner showed her love for denim when she stepped out to eat dinner at the Sarafina Restaurant in Soho, New York, in March 2017. We love a good denim jacket, but this head to toe look is a bit overboard.

Is that long belt made for a giant? This outfit is perplexing. Too much is like not enough, as we say.

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24 Fur Fiasco

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian showed off her curves into a nude bodysuit while vacationing in Iceland in April 2016. The fur coat seems out of place with that unitard.

The Yeezy tennis shoe boots only add to the confusion. This outfit is all over the place, and there is really nothing we like about it. Go back and change, Kim!

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25 Wardrobe Whoops

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kris Jenner had a bit of a wardrobe malfunction while out in Los Angeles, California in June 2017. The photographer’s flash bulbs exposed her nude slip.

Although, we can’t help but wonder if she took a note from Kourtney and did this on purpose? We wouldn’t put it past her.

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26 Bizarre Biker Shorts

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian went through a phase of wearing biker shorts as street fashion. The paparazzi captured her in this frumpy look as she went to Watts Empowerment Center to receive the “Key to our Heart” for her family’s donation to the program in March 2018.

Did she just leave the gym? How is this considered fashionable?

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27 Hideous Hoodie

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kendall Jenner wore this kooky outfit on the streets of London in February 2017. This is another head-scratcher because she always stays on trend.

If the baggy sweater wasn’t enough, the gold tooth seems so random. Maybe she suffered from jet lag? The only valid reason to wear this sweater is if it was made by her lovely grandmother.

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28 Cowgirl Fringe Fail

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian went Western chic at the Balmain PFW dinner of the Paris Fashion Week in March 2015. That fringe is out of control.

Sorry, Kimmy. This outfit is so bad that even Kanye looks baffled by it. And it looks like the blonde hair adds to the bad look, don’t you think? It could be an interesting costume for a figure skating number, though.

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29 All Torn Up

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Khloe Kardashian jumped on the shredded jeans trend, but took it a bit too far while running errands in Los Angeles. Holey jeans can be cool, but these just look trashy.

Some poor stylist must have slipped when they were shredding these with scissors. That’s the only logical explanation.

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30 Robin Hood

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It’s so fun to look back at Kim Kardashian’s outfits from the early 2000s. She actually wore this belt and boot ensemble to a Jay-Z release party in Hollywood, November 2006.

Her hair and makeup are just as awful as this outfit. Was Robin Hood inspired red carpet wear ever a thing?

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31 Camo Glam

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kylie Jenner mixed fashion with outdoor wear when she posted this pic of her in a camo shirt and a gold belt on Instagram in September 2016. These two things just don’t go together.

Quit trying so hard, Kylie. You won’t win any fashion wars with this look. Unless it’s a worst outfit contest, then you’d have a chance.

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32 Peplum Problem

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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We can all learn a lesson from Kim Kardashian’s peplum pants fiasco. She was spotted wearing python peplum pants in Los Angeles in 2013. This is yet another maternity look gone wrong.

The frilly top just adds volume to her curvy frame. This is a major fashion flop!

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33 Fashion Week Fail

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Kendall Jenner walked the Marc Jacobs Autumn 2017 show at Park Avenue Armory in this confusing outfit. We get they styled her for the fashion show, but this is just not a good look on her.

It’s a lot to take in. From the puffy wool hat to the chunky platform shoes, this outfit is ridiculous from head to toe.

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34 Invisible Boots

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Kim Kardashian sported these terrible thigh-high clear boots during a trip to New York City in 2016. She completed the hideous outfit with a sheer bra, denim cut-off shorts, and a huge denim jacket.

We can only imagine how sweaty she got in those plastic boots. It’s like a walking sauna for her legs. Yuck!

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35 Farm Chic

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kris Jenner normally looks flawless, but this outfit is just a fashion no. Photographers captured the “Momager” walking to the family office in Los Angeles in black overalls in April 2014.

Those chunky black and white sandals aren’t doing her any favors. Who knew Farmer Kris was even a thing?

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36 All That Glitters

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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Kim Kardashian paired a leotard with glittery stockings and high heels while going out to dinner during the 2019 Paris Fashion Week. She topped the whole thing off with a long black coat.

This shimmery look just seems awkward. Does anybody else think she looks like she’s on her way to audition for the Rockettes?

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37 Revealing Lace Dress

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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To visit the Vatican City, on July 1st, 2021, Kim Kardashian decided to wear a white lace dress rather revealing. We strongly doubt that this is a look suitable for such a visit.

In the caption of her Instagram post, she still wants to reassure her fans, though. She wrote, “Don’t worry, I adhered to the dress code and fully covered up while inside St. Peter’s Basilica and the Sistine Chapel’s”.

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38 Track Pants And Boots

Countless Times The Kardashians Made Hilarious Fashion Mistakes
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The paparazzi snapped a pic of Kendall Jenner committing a major fashion crime. The Keeping Up with the Kardashians star paired Adidas track pants with snake-skin boots.

We get trying to dress up athletic wear, but this look just isn’t working. Someone should’ve stopped her from going out in public looking like such a hot mess.

Leigh Hewett

Freelance writer and pop culture junkie, Leigh Hewett loves to keep her finger on the pulse of celebrity news. Her work has been featured on TheTalko, Babygaga, and TheRichest. Her hobbies include keeping up with the Kardashians, eating french fries, and driving her two sons to and from basketball practice, all while blasting 90s hip hop from her minivan.

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