The Kardashian-Jenners—that's Kim, Khloe, and Kourtney Kardashian, Kylie and Kendall Jenner, and occasionally their matriarch Kris Jenner—have made a business out of their red carpet looks. They can be categorized as "too much"—too naked, too sheer, too over-the-top—but every time we start to think we've seen it all, they break out a new vintage piece, a surprising silhouette, or a daring aesthetic that just can't be ignored. The Kardashian-Jenners have been red carpet mainstays since the '00s and '10s, and they're always getting us talking. The three big players are Kim, Kendall, and Kylie, who sometimes seem like they're in a competition to outdo each other, but just as often pose together in their looks as a very fashionable family.
So which looks are the best, most dramatic, most-talked-about moments? There are a plethora to choose from, but—whether it's from some scandal or because it's the most daring red carpet look we've ever seen—here are 32 of the wildest red carpet moments they've ever given us.
Kanye West, Kim Kardashian, and...Amy Schumer at the TIME 100 Gala
Dramatic for very different reasons than avant-garde fashion, Kim (along with then-partner Kanye) were walking along the red carpet when Amy Schumer decided to throw herself in front of them on a whim. She later told Graham Norton that she looked back and saw them, "Kim and Kanye standing there, just owning it, just being short and important. And I think falling is the funniest thing, so I took a dive in front of them.” She said Kanye in particular was unamused, and added, “There’s no way that either of them had any idea who I am...So that was comforting.”
Kim Kardashian at the 2018 MTV Movie And TV Awards
In February 2018, Kim came under scrutiny for wearing her hair in Fulani braids and calling them "Bo Derek braids." Later that year, she wore the style again and was asked about people's commentary. "I actually didn't see backlash. I actually did that look because [Kim's daughter] North said she wanted braids and asked if I would do them with her. So we braided her hair and then we braided my hair." But she did add of the earlier incident in February, "I obviously know they're called Fulani braids and I know the origin of where they came from and I'm totally respectful of that...in no way am I ever trying to disrespect anyone's culture by wearing braids. If anything, my daughter was so excited to see me get matching braids with her. [When] we did her hair in these braids, she was so excited."
Kim Kardashian at the Hollywood Beauty Awards in 2019
This vintage Thierry Mugler is both an impressive commitment and...something that looks pretty uncomfortable if we're being honest. (It's originally Haute Couture Spring/Summer 1998, and not the first time someone has reused vintage Mugler, but this feels like the most notable.) This is also not the first time Kim has opted for the over-the-top, avant-garde late designer for her most daring looks, but it began a multi-dress run that gave us both a dripping wet Met Gala look and a futuristic silver dress.
Kylie Jenner at the January 2023 Schiaparelli Paris Fashion Week
Leave it to the Kardashian-Jenners that, for one second, people wondered—wait, is that an actual lion head Kylie Jenner is wearing?? It's not, of course. At Daniel Roseberry’s spring 2023 Haute Couture collection for Schiaparelli, the models walked with wildlife outfits (including leopard, wolf, and Irina Shayk in Kylie's lion dress). Kylie sat in the front row of the show—a little celebrity synergy there—and later took to Instagram to clarify that, contrary to popular opinion, those were not real animal heads: "Wow i loved wearing this faux art creation constructed by hand using manmade materials."
Paris Hilton and Kim Kardashian at the 'Entourage' Los Angeles Premiere, 2006
In case you're only familiar with Kim via SKIMS, her Hulu show, and Instagram, let me be the first to share with you this iconic photo. One of Kim's first appearances on any red carpet was with Paris Hilton as a sidekick of sorts. People claimed that she was Hilton's assistant, but Kim told Andy Cohen, "I would work with Paris, and I would love to organize and clean out their closets and get rid of all their stuff and sell it on eBay and then shop for them, shop for her. That was my job. I loved it. But people will say 'assistant.' They always have it wrong."
Kim Kardashian at the 2006 US Weekly's Hot Hollywood: Fresh 15
Kim's early red carpet appearances were...a real feast for the eyes, let's say. This is an onslaught of perhaps regrettable '00s fashions: big, chunky black belt that didn't really need to be there, long tunic dress with layers underneath, knee-high boots, and teased hair just for funsies. To be clear, Kim wasn't the only one dressing like this, but before she hit the mainstream, her outfits were a lot less curated and a lot more whimsical. And there's a part of me that misses the spontaneity—I promise!
Kendall Jenner and Kylie Jenner at the Premiere of 2011's The Twilight Saga: Breaking Dawn - Part 1
Early red carpet days for the Kardashian-Jenners were both funny and sweet. The fresh-faced Kendall and Kylie here (at one of their first red carpet events ever—a Twilight movie, naturally) are embodying '10s fashion so very much. The chunky peep toe heels, the random (and totally unnecessary) off-the-shoulder detailing on Kendall, some visible bra action, and a lot of asymmetry in the hems: It's all here. Obviously, Kylie and Kendall would rise to incredible sartorial heights after this, but I like the reminder of how far they've come.
Khloe Kardasian, Kylie Jenner, Kris Kardashian, Kourtney Kardashian, Kim Kardashian, and Kendall Jenner at the Kardashian Kollection Launch Party, 2011
Look at all this matching! There is a lot of pattern mixing going on here, primarily leopard and black and white; it's very fitting considering that in the early days of the matching-K-named sisters, everyone was walking the red carpet as an up-and-coming famous family. (One of the things that makes me quietly lol is the matching black platforms that truly all of them are wearing.) Given their later careers, the Kardashian-Jenners are probably either laughing at these photos or quietly wishing they could scrub them from the internet, but I appreciate it as the throwback it is.
Kim Kardashian in Soho, 2016
Ok, so, I grant you that this is technically not a red carpet event (one could argue that Kim Kardashian makes everywhere her own personal red carpet, but still). And yet I cannot stress enough how these clear thigh-high boots set the '10s internet aflame. People had a lot of questions. Were they as sweaty as they looked? Did they keep her dry, especially if it rained (could you actually call them rain boots??)? Were they uncomfortable? Could a normal person wear them? Kim did not answer these questions, and, truly, the mystery remains.
Kim Kardashian at the 2018 Met Gala
All the Kardashian-Jenners have made the Met Gala their own personal opportunity to wear the most daring outfits they possibly can. This one isn't even all that wild, relatively speaking. The theme was “Heavenly Bodies: Fashion and the Catholic Imagination” and Kim fittingly wore a Versace with cross detailing—it fit her body perfectly, and is actually a pretty phenomenal choice for the theme. This certainly wasn't Kim's first Met Gala, but it would start a multi-year run of pretty cool outfits for the star.
Kylie Jenner at the Marie Claire Image Maker Awards 2017
Like her older sister Kim, Kylie's known for some over-the-top red carpet gowns. This one was a trifle mystifying, with the cutouts on her frilled purple skirt starting at the side of her hips and ending right below her...knees? It's from Balmain's Resort Collection, and it marked Kylie's return to social media after some time away. The dress naturally spawned some comparisons to a muppet (Grover? Anyone?) but it's also pretty par for the course for Kylie's skin-baring and daring red carpet style at this point.
Kendall Jenner at the 2016 MTV Movie Awards
Can you imagine doing anything in these heels?? The high-low dress is Kristian Aadnevik, and (in case you're curious or want some for yourself) the lace-up heels are DSquared2. In a since-deleted Instagram post, Kendall captioned her prep photo "Team Work," which makes sense because it would take a lot for anyone to lace up those sandals—much less keep them up. Kendall, who was by then a Victoria's Secret model and on the rise towards supermodel-dom, somehow pulls this OTT style off.
Kim Kardashian at the 2016 Met Gala
For the "Manus x Machina" themed Met Gala, Kim went for a silver, studded, gorgeous Balmain. She called the look "blingy, sexy, robot," which inspired a lot of memes and headlines in equal measure. (Also headline making? Kim's partner at the time, Kanye, showed up in a silver matching jacket, very ripped jeans, and scary blue contact lenses.) Kim loves a sparkly gown to the Met Gala, starting with the previous year with a semi-naked Roberto Cavalli dress and continuing for the next several years.
Kendall Jenner at the 2022 LACMA ART+FILM GALA
These days, the Kardashian-Jenners love to deploy a sheer, semi-sheer, or barely-there outfit at a lot of their red carpet events. Kendall here is no exception, with her black, silver, sheer Burc Akyol gown feeling...a little haphazard, I'm gonna be honest. I love the silver skirt, and I don't even mind the leather-esque straps on top, but the two strips of fabric around her naval confuse me a little. Kendall posed with Kim, who was also at the event in a skin-tight black gown that was extremely fitting for her style.
Kylie Jenner at the 2019 Grammys
People were pretty divided on this (general consensus at the time was that it was a lot of pink and the gloves were an intriguing choice). It's a sculptural Balmain Couturepink jumpsuit—say that three times fast—with matching gloves and a silver belt. There with then-boyfriend Travis Scott (in a black suit), who was nominated, the two had a PDA-filled red carpet. To be honest, it's not the strangest thing or the most OTT thing Kylie has ever worn, but she always knows how to own the red carpet.
Kendall Jenner at the 2017 Met Gala
Also known as "the year Kendall Jenner went to the Met Gala in a thong," this semi-naked dress is utterly impressive given how tricky it is to pull off. This glittery La Perla slip dress has a low back and a very '00s visible black thong in the back, which (along with red bottomed shoes) meant that the dress had a fun surprise when she turned around. Let's be clear that naked dresses are not a new thing—Cher was rocking 'em way back in the '70s—but this evolution had a cheeky (pun intended) sense of humor about it.
Kylie Jenner at the 2022 Billboard Music Awards
Taking the "naked dress" in a different direction entirely, Kylie attended the awards with Travis and Stormi in a graphic printed Balmain dress that gave the illusion of a female figure. (Stormi, who's often in matching outfits with her mom, was in a white tube dress and high-top sneakers.) It's not the first time a Kardashian has worn this type of dress, but this certainly a chicer version of it—and actually meaningful, since the collection was meant to be a commentary on the dysmorphic vision of one's bodies that can result from social media.
Kim Kardashian at the 2020 Vanity Fair Oscar Party
Kim's look at the Oscars after-party (a gift from Kanye) was also a cool vintage fashion moment: It's Lee Alexander McQueen’s famed “Oyster dress” from 2003. Per Vogue, "Crafted with boned tulle and silk chiffon artfully shredded and arranged to replicate the shape of an oyster’s shell, the dress captured that feeling [the show's focus on the dangers of change] perfectly." Apparently Kim had to lie on the floor of the limo to preserve the dress, and it's one of her best vintage pulls to date.
Kendall Jenner at the LOVE Magazine LFW Party, 2020
It's not just Kim who loves vintage! After walking in the Burberry show, Kendall gave us this sheer butterfly dress—which is vintage Jean Paul Gaultier—for a night on the town in London. The Kardashian-Jenners love their sheer printed material, but this one is a special standout for its eye-catching pattern. She revisited her love of a vintage '90s John Paul Gaultier in 2021; Kim is also a big collector of vintage John Paul Gaultier, and Kourtney has also worn him, so this piece is technically part of a larger family tradition.
Kim Kardashian at the Hulu Premiere of "The Kardashians" in 2022
Kim loves the bombastic style of the late designer Thierry Mugler, and this is one of the most futuristic and advanced dresses for her. This silver latex dress was made custom for her (naturally), and the stacked silver necklace and silver bangles at her wrists just adds to the general vibe of looking like a cool, sexy robot—she drew comparisons to a fembot, of course. The whole family was there for the premiere, and there was a lot of black going on, so Kim also made sure that she stood out with the dress.
Kendall Jenner at the 2019 Vanity Fair Oscar Party
I don't know if I've ever considered a loincloth to be high-fashion, but here we are! Since Kendall is a literal supermodel, she can absolutely pull off a look with slits going all the way up to her groin (she almost flashed the photographers when she turned to the side—and it was a very meme-able moment, naturally). The black Rami Kadi couture gown also drew comparison to that gown where Angelina Jolie stuck her leg out—except in this case, it's both legs, and a whole lot more skin!
Kylie Jenner, Kim Kardashian West, and Kendall Jenner at the 2019 Met Gala
The Met Gala was a family affair! The theme was "Camp: Notes on Fashion," and...I see how these are all campy, yes! Kim is in Thierry Mugler, in the now-infamous "wet look" and highly corseted gown. Kendall is in a sheer beaded Versace with feathered ruff extended all the way down her arm. Kylie (in matching purple hair of course) is also in Versace, with feathered arm ruffs that brought some serious volume—Vogue called it "showgirl-slash-mermaid." The three posed for a lot of photos, and each, while completely different, really brought the drama.
Kris Jenner at the 2019 Met Gala
Along with her daughters (everyone competing for the most dramatic look of the night), Kris came to the Met Gala in a cool look too. Kris doesn't always go wild on the red carpet, often opting for classic shapes and color, but this was the exception. The blonde bob made her look completely unrecognizable, and she paired her Tommy Hilfiger jumpsuit with a silvery gray tulle jacket that extended all the way to the floor. She said she highly recommended pants at the Met Gala, and said, "I’m channeling David Bowie going to the opera,” to Vogue.
Kim Kardashian at the 2022 Vanity Fair Oscar Party
This bright blue Balenciaga is a serious gown on Kim (although the shades are a nice casual touch, lol). The sleeves turn into gloves (which is one of her big moves, as well as one her sisters like to pull off too), and this has a cool long train. You can't really see it in this photo, but the dress opens up in the back—and looks more like swimsuit chic from that angle. Kim didn't go to the Oscars that year...but Kourtney did, with partner Travis. "This is so iconic," Kim wrote on Instagram alongside a bunch of crying emojis. Apparently her commentary on her stories resulted in her invite here!
Kendall Jenner at the amfAR Cannes Gala 2019
Proof that there was pink before Barbie! This might be one of my favorites of Kendall's big red carpet style. This was a pre-Cannes Gala, and the dress is part of the Giambattista Valli x H&M collection. Because it's a high-low construction (and because Kendall knows how to pose), there was a lot of leg action—as we see here in this photo. Kendall seemed even more delighted than usual to be modeling the gown, and she walked with designer Giambattista Valli. Honestly, it's iconic, and I love it.
Kim Kardashian at the 2023 LACMA Art+Film Gala
Hello, train! And hellooooo pink! Whether or not she was inspired by the Barbie movie, the Kardashian-Jenners (as well as other celebrities) can sometimes use the LACMA Gala to break out some big looks. This is a Balenciaga 52nd Couture gown, and honestly I love the old Hollywood glamour vibes on her. Kim broke out some gloves, as she often loves to do, and drew comparisons to Marilyn Monroe. In a star-studded event that included Jennifer Lopez, Leonardo DiCaprio, and Lenny Kravitz, she stood out.
Kendall Jenner, Kim Kardashian, and Kylie Jenner at the 2023 Met Gala
The Kardashian-Jenners made the 2023 Met Gala ("Karl Lagerfeld: A Line of Beauty") a major event. Kim's dress was custom corseted Schiaparelli dripping in pearls, Kylie's was red Jean Paul Gaultier, and Kendall's was a signature no-pants look with a black glittery bodysuit and loooong sleeves that turned into two trains (don't forget the huge platform boots!). There had been rumors that the Kardashian-Jenners hadn't been invited to the Met Gala this year, so it probably wasn't a coincidence that there was even more posing than usual.
Khloé Kardashian and Kylie Jenner at the 2022 Met Gala
Kylie and Khloe wore strikingly different outfits to the 2022 Met Gala. Kylie's was probably the more daring and controversial, with the Off-White gown looking both bridal and princess-y in equal measure. Of course, the baseball cap (with matching veil) definitely brought in...a more casual vibe, let's say! Khloe wore a semi-sheer gold gown by Moschino, with contrasting black long opera gloves and matching black shawl. When asked about her look, Khloe said, "We did it in like 10 days. [Moschino creative director] Jeremy [Scott], I love you. It's fab."
Travis Barker and Kourtney Kardashian at the 2022 Met Gala
The Kardashians: always bringing their partners to the red carpet! Kourtney made her Met Gala debut with husband Travis Barker in matching Thom Browne skirts. For a Met Gala that saw a lot of intense Kardashian-Jenner looks, this one still rose above the rest. Barker wore a kilt-like construction, but Kourtney's was the more daring (and kind of confusing) with a cream body-con construction around the waist and deconstructed kilt attached at the bottom—plus a crop Oxford shirt on top. But I actually appreciate that the two outfits have some similarities, just with different aesthetics.
Kim Kardashian at the Met Gala, 2013
One of Kim's early meme-able moments (she drew a lot of comparisons to a couch), the pregnant star wore a Givenchy floral dress that covered every part of her except her neck and head for her Met Gala debut. She later told Vogue, "I was very pregnant, very puffy, and bloated and I was like, 'Oh god, of course the first time I go I'm gonna be huge'.” She added that once she realized she was being made fun of, "I was crying, like, the whole way home because I just couldn’t believe it. There were all these memes about me and this couch!"
Kim Kardashian at the Met Gala, 2022
Kim debuted one of her most controversial looks of all time at the 2022 Met Gala, which was themed, "In America: An Anthology of Fashion." She later noted to Vogue that nothing felt more American to her than Marilyn Monroe, and so she literally coordinated to wear Monroe's "Happy Birthday Mr. President" dress (which she was only able to wear for a dew minutes since it's literally a historical artifact). It looked in photos like she might have damaged the dress, but the Metropolitan Museum released a statement debunking that rumor. Kardashian noted that she was very respectful to the garment, adding, "I would never want to sit in it or eat in it or have any risk of any damage to it and I won’t be wearing the kind of body makeup I usually do."
Kim Kardashian at the Met Gala, 2021
This, for the “In America: A Lexicon of Fashion" Met Gala, Kim was barely recognizable at all in a head-to-toe black Balenciaga (quite literally including her head). She later told Vogue she fought the look obscuring her face, telling Vogue, "But [Balenciaga’s creative director Demna Gvasalia] and the team were like, 'This is a costume gala. This is not a Vanity Fair party where everyone looks beautiful. There’s a theme and you have to wear the mask. That is the look.'" Gvasalia added the mask was "conceptually speaking, quite important...people would know instantly it was Kim because of her silhouette."
