19 Unforgettable Style and Beauty Moments from the Past 13 Years of Keeping Up with the Kardashians

When Kim Said Her Sisters Looked Like Clowns

Kim didn’t hold back her feelings when Kourtney and Khloé experimented with their glam during their trip to Japan in 2018. “You guys, you look like f—ing clowns. I’m not f—ing kidding,” Kim told them during a sister sit-down the morning after they got decked out in looks she didn’t approve of. “This is not a tourist thing where it’s like, Halloween, dress up like a f—ing Japanese geisha, unless we’re at a geisha house.”

Kourtney thought her look, which included a cobalt smoky eye, was “was fun for Japan,” but from Kim’s perspective, she missed the mark. She added her outfit “would have been great” if she made a few changes to her overall look: “If you didn’t have f—ing blue eye shadow,” said Kim.

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When Kim Accused Kourtney of Copying Her Style

Things got heated between the sisters when Kourtney was looking for an outfit to wear for her 40th birthday party. In her confessional, Kim explained that she works hard to maintain close relationships with the designers she borrows dresses from, and she doesn’t think Kourtney appreciates that.

“I don’t think Kourtney understands the legwork behind this. I don’t think anybody understands. You have to really have a relationship with that designer. She has no idea how this works,” Kim said.

Kourtney defended herself and her stylist, who at times has requested dresses from designers that Kim wanted to borrow too. “We have completely different looks. I’m not trying to copy your styles. But on a same designer, you can’t ban me from [them],” she said on the phone to Kim.

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When Kris Got Earlobe Surgery

The family matriarch has never been afraid to document her cosmetic procedures (who can forget her facelift before Kim’s wedding?), so when she noticed her earlobes beginning to droop, she didn’t hold back her thoughts in a 2018 episode of KUWTK. 

“All I want is just cute ears. Ever since Kim made a comment about my ears I’ve always wondered and now I am looking in the mirror obsessively like, ‘Are they too big?'” Kris said. 

She ultimately went under the knife, and her family loved the results just as much as she did. “Your ear looks like a normal ear now!” Kim said when she saw her mom’s new earlobes.

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When Kim Gave Khloé a Style Makeover

Each of the Kardashian-Jenner sisters have developed their own unique sense of style, but back in 2017, Kim didn’t hold back her thoughts about Khloé needing some extra work in the fashion department. “I always cringe when I look at Khloé in outfits. You know what, she’s so trendy, and I used to be that way but she is like that on steroids,” Kim said.

So the SKIMS founder decided to take things into her own hands and secretly pack her sister’s bag for a trip to Santa Barbara — while managing to overhaul her look. 

“I think I can just help Khloé have more simple style cause her body really is the accessory,” Kim said.

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When Kim Practiced Mortician Makeup on Kris

The Kardashians always get into some pretty outlandish escapades, but nothing was more surprising than when Kim considered getting into mortuary makeup in 2018. And since Kim had only done her makeup on herself before, she had her mom Kris stand-in as a faux corpse so she could practice her skills. Typical family activities, right?

“Obviously my mom’s not like, a substitute for a dead body,” Kim admitted. “But I’m just so used to doing makeup on myself I just need somebody to test it out on.”

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When Kim Lost Her $75,000 Diamond Earring in The Ocean

Who can forget the infamous moment on a family trip in Bora Bora when Kim had a meltdown after then-boyfriend Kris Humphries playfully tossed her in the ocean – and caused her pricey diamond stud to fall out in the process? Maybe that’s why the marriage only lasted 72 days.

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When Kim Stripped Down For Playboy

Kris was on board from the start, but Kim wasn’t so sure about posing for Playboy so soon after the negative publicity around her leaked sex tape. Ultimately, she agreed to be shot semi-nude with pearls draped all around her body, giving us a memorable December 2007 cover and one of the greatest Kris Jenner memes of our time.

“I mean I’m sure she’s not just standing there with her boobs out,” Kourtney said to Khloé while Kim was at the shoot. Nope, because she saved that for Paper magazine!

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When Kris Got Really Drunk and Tattooed Kendall and Kylie’s Names on Her Back

Someone plays favorites! While Kim fought with Kourtney and Khloé over ruining her “Bentley moment,” Kris got drunk with one of her friends and decided to tattoo her lower back with Kendall and Kylie’s names flanking a cross.

“Well, I’m mad at Kim and Kourtney and Khloé, so I’ll just do Kendall and Kylie,” she said. Wait a second, what about Rob?!

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When Khloé Would Rather Go Naked Than Wear Fur

Kim isn’t the only Kardashian sister to bare it all — Khloé had her own nude shoot during season three when she starred in a campaign photo for Peta’s “I’d Rather Go Naked Than Wear Fur” initiative. Since then, the star has disaffiliated herself from the organization after Peta anti-fur protesters pelted Kim with a flour bomb in 2012.

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When The Sisters Did Their First Swimsuit Shoot Together at Joe Francis’ House

The sisters (and Kris, duh) jet off to Puerto Vallarta for an Ashley Paige swim shoot at Girls Gone Wild creator Joe Francis’ house without telling Caitlyn. Caitlyn flies down to Mexico, crashes the shoot and drama ensues. Oh, and of course Kris pops in for a few shots, because why not. Classic season one antics on KUWTK!

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When Kim Cried Over Her Semi-Nude W Magazine Shoot

Long before Kim bared it all on the cover of Paper magazine, her W magazine cover (portraying the star nude in a pool of silver paint) caused tears on season one of Kourtney and Kim Take New York. “I’m so f—king mad right now!” she sobbed on the phone to her momager Kris Jenner. “[They] promised me I would be covered in artwork on top of me. It was so uncomfortable. I’m really honestly freaking out.”

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When Kylie Got in Trouble For Wearing Too Much Makeup

Before she built her $1 billion Kylie Cosmetics empire, Kylie was just your average 11-year-old girl experimenting with makeup. But as the youngest child in the family, Kylie’s dad wasn’t having it. When Kylie showed up to dinner with a full smoky eye, heavy liner and red lipstick, her dad freaked. “She’s dressed like a 30-year-old and eating like an 11-year-old,” Caitlyn said.

“You gotta deal with your kids growing older,” Kris replied. “No. She’s 11 years old and she shouldn’t be wearing all that makeup and she shouldn’t be wearing that outfit and that’s the bottom line,” Caitlyn said.

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When Kim Started to Show Signs Of a Shopping Addiction

It got so bad, Kourtney and Kris took Kim to the mall and challenged her not to buy anything. But of course, Kim couldn’t last one visit to Bloomingdales without making a purchase, and was caught red-handed sneaking back into the dressing room to buy clothes.

“I am adult. I can do whatever I want!” she said when her mom and sister busted her. “That’s what an addict would say,” Kris replied.

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When Half of Kourtney’s Face Froze

Kourtney wouldn’t let a half-frozen face stop her from a good time. The star met Khloé for lunch after she got anesthesia at the dentist … that didn’t quite wear off in time. “What is that mug on your face?” Khloé laughed. “I can’t really talk cause I had my face numbed,” Kourtney replied.

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When Kanye Cleaned Out Kim’s Closet

When Kim started dating Kanye, the world noticed a major style change. Gone were the KUWTK star’s leopard print looks, chunky belts and curve-accentuating bodycon dresses, thanks to the help of the Yeezy designer and his stylist.

“Babe you really gotta like, clean out everything,” he told her on the show. (She cried, but she appreciates it now.)

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When Kendall Snuck Off To Vegas And Almost Got a Tattoo

For her sweet sixteen, the soon-to-be-supermodel headed to Vegas with Kylie to get a tattoo without her parent’s permission. But once she got in the chair, Kendall started having second thoughts and called Kourtney, who eventually talked her out of it.

“I know it’s exciting to do something so you can show everyone. That’s what I did when I got my boobs done. Afterwards, I regretted it so much,” Kourtney told her over the phone. “It’s a tattoo. It’s there forever.”

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When Kris Forgot About Kourtney’s First Cover Shoot

Kris got so caught up with Kim’s exciting appearance at Comic Con for her role in Disaster Movie, the momager forgot about her eldest daughter’s first magazine cover shoot for 944 magazine. Luckily, Khloé came to the rescue and cheered Kourtney on from the sidelines.

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When Kim Got Psoriasis

By now, Kim’s an expert at managing her psoriasis, but her initial outbreak caused a panic. “Khloé seems to think that I have ringworm and I don’t even know what that is,” Kim told dermatologist Dr. Lancer. “Imagine what the tabloids would do to me if they saw all these spots!”

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When Kim Took Selfies During The Car Ride to Drop Khloé Off at Jail

And of course, we can’t forget that time when Kim’s selfie obsession led her to take some snapshots to capture the moment the family drove Khloé to jail.

“Kim, would you stop taking pictures of yourself?” Kris famously said. “Your sister’s going to jail! Have a little compassion!”

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