The Kardashians' Most Awkward Red Carpet Moments Ever

As total red carpet pros, Kim Kardashian, Kourtney Kardashian, Khloé Kardashian, Kris Jenner, Kendall Jenner, and Kylie Jenner may seem like the coolest sisters in the game when it comes to stepping out in front of the cameras, but no one's immune to an awkward moment — including this famous family. There have been many big moments for the gang when it comes to hitting the red carpet over the years, including debuting new romances, showing off their babies, promoting their latest business ventures, and so much more, but even if you're a gorgeous and rich Kardashian, things don't exactly go smoothly when the cameras start to flash. And we have the proof.

So hold on to your Skims, slip on your Good American jeans, and grab that Kylie Cosmetics lip kit as we take a stroll down memory lane with the first family of reality TV to remember some of the most awkward moments from the step and repeat line that we're literally still cringing over. Bible.

Well, this was awkward. In November 2019, the Kardashians came out in force for the People's Choice Awards, and Kim Kardashian, Kourtney Kardashian, Khloé Kardashian, and Kris Jenner all chatted with E! host Giuliana Rancic on the red carpet. As Rancic inquired about their uber-glam outfits, cue Kim thinking her big sister had forgotten her outfit's designer while swooping in to help her out. Or so she thought.

Kourtney tried to answer Rancic's question, saying, "I didn't plan this... Naeem Khan? Is that how you say it?" as she rocked Khan's crystal stripe easy suit. That's when Kim stepped towards Rancic with her arms out, speaking over Kourtney to draw attention back to her, pointing out they were all wearing her new KKW fragrance. Kim then told a perturbed Kourtney, "I was saving you since you didn't know who you were wearing. That was my save," to which Kourtney hit back, "No, it's Naeem Khan, I just didn't know how to pronounce it." The most cringe part of all? Kim's awkward, "Oh."

Fans clearly noticed the awkwardness between the family, with some even pointing out the stern face Kris gave Kim. "I love them! But Kris face when Kim cuts her off! I think my mom given me that face too like, '[you're] still talking,'" one person wrote in the YouTube comments. "Kourtney was just taking her time to talk, she didn't need saving hahaha this is why they fight," another commented.

This one's awkward in a whole different way, as we take a look at the time Kourtney Kardashian and her fiancé Travis Barker walked the red carpet at the 2022 Oscars on March 27, 2022. The two looked seriously loved up (it's no surprise Kourtney and Travis married in a secret, not legal Las Vegas ceremony just a few days later!) and showed off plenty of PDA on the main event and the Vanity Fair after party, with that alone having plenty of fans feeling, well, pretty darn awkward and grossed out.

The things that made the whole thing even more awkward? Many couldn't actually work out why Kourtney and Barker were even at the Oscars to begin with. "I have no idea what these two are doing here. Why on earth were they invited?!" one person asked on Twitter, while another questioned, "Why are Kourtney and Travis at the oscars and why can't they go 5 minutes without making out." In case you were wondering (which we're sure you were) the couple were there because Barker was invited to be part of the Academy's band for the evening.

Kourtney's appearance also sparked rumors of tension with Kim Kardashian, with a source claiming to The Sun, "She isn't jealous of Kourtney necessarily but I think it stings a little that she was invited to the Oscars because Kim has always been desperate to be accepted by the Hollywood elite and wants to be taken seriously."

What's more awkward than a prankster on the red carpet? Well, Kim Kardashian (probably) asked herself that question back in September 2016 when she was attending Paris Fashion Week and fell victim to Ukrainian prankster Vitalii Sediuk. Shocking paparazzi video shows Kim getting out of her car with a bodyguard by her side, before Sediuk came out of nowhere and lunged at her. Fortunately, though, he just missed the star and was instead wrestled to the ground by security. After a few seconds, he was allowed to get up and fled the scene. However, she wasn't so lucky two years later when Sediuk actually seemingly made contact with her as she exited her car before a fashion show, causing Kim to be grabbed by security.

Sediuk claimed on Instagram in a since-deleted post in 2016 that he was apparently trying to kiss Kim's booty (not that that makes this situation any better), telling the world he was protesting butt implants (something Kim has always denied having). "I encourage her and the rest of Kardashian clan to popularize natural beauty among teenage girls who follow and defend them blindly," he wrote in the caption, per LadBible. He also alleged the incident wasn't premeditated. Sure, Jan.

Kim wasn't the only star he's targeted, either. Sediuk was the guy who tried to kiss Will Smith on the red carpet in 2012 and attempted to snatch the mic from Adele at the Grammys in 2013.

As if someone trying to kiss your butt on the street wasn't bad enough, Kim Kardashian has also had to deal with being covered in flour on the red carpet. You might remember this one from back in 2012 (it was a pretty big deal!) and saw Kim doused in the white stuff while she walked the red carpet for her perfume launch in Hollywood, coating her hair and black blazer. As if that wasn't bad enough, the person that did it reportedly shouted "Fur Hag," per TMZ, and they were then detained, though Kim chose not to press charges.

There was a whole lot of speculation over who the assailant was and why they dirtied Kim up, with it later being revealed they were an avid supporter of PETA but not necessarily associated with the animal rights group themselves. "It was not [us]. We were given the video by an anti-fur activist on the scene," PETA told TMZ.

However, Kim's sister, Khloé Kardashian, wasn't buying that, and cut ties with the company following the incident. "I just received word that the woman responsible has very close ties to PETA, despite PETA publicly stating otherwise. Not only has PETA lied to the public, but they have proved that they support this kind of behavior," she claimed on her blog, per The Hollywood Reporter. Khloé added, "Bullying and harassment is NEVER a solution, and I won't be a part of any organization that thinks otherwise."

It's not just the Kardashian side of the family that have had their fair share of awkward moments on the red carpet, as the Jenners have proven they're not immune to a cringey experience either. Case and point? Kendall Jenner's run-in with an Australian interviewer in 2019 that was so bizarre she was genuinely concerned for him. This one went down as part of "The Kyle & Jackie O Show" when Kendall attended the opening of a new Tiffany & Co. store and was originally posted to Twitter, but has since been deleted (too awkward for social media, perhaps?) though you can see it all go down via Daily Mail.

This one got awkward after the interviewer, identified only as Intern Pete, was clearly nervous to chat with the superstar. He asked her a bunch of questions very quickly and told some information about his personal life that appeared to leave Kendall a little out of sorts. "Sorry, I'm running a little bit slow, I'm out of back surgery so I'm on light duties at the moment," he said, to which Kendall apologized and said, "What? Oh my goodness. Are you okay?"

Intern Pete took it all in his stride after the interaction went viral, though. "I think you were thrown by her beauty. Even though you're gay you were saying just how beautiful she was," Jackie O said on "The Kyle & Jackie O Show," to which Pete joked, "Yep, 100% straight now. She is stunning."

Proving the ultimate momager even gets confused sometimes, this red carpet awks moment involves Kris Jenner throwing in her two cents regarding the fashion at the 2017 Oscars — while also having no idea about an important show of solidarity from those in attendance. Plenty of attendees wore a blue ribbon to show their support for the American Civil Liberties Union (ACLU), though Kris didn't know that. She appeared on E!'s "Live From The Red Carpet" coverage alongside Giuliana Rancic and asked as they discussed Ruth Negga's ensemble, "What is the little blue thing she has there? Is that a ribbon?" A seemingly surprised Rancic then set Kris straight, to which Rancic responded, "Oh, it is?" after Kris claimed that was the first one she'd seen on the red carpet that night. Things then seemed to be a little flustered as Rancic attempted to direct people to where they could learn more about the organization, while Kris looked a little awkwardly off camera.

But Twitter wasn't about to let this one go. "CAN WE REWIND GIULIANA EXPLAINING THE ACLU TO KRIS JENNER BECAUSE," one person wrote in all caps, while another tweeted, "Kris Jenner is so out of touch she doesn't know what ACLU is! Talk about privilege!" The ACLU itself also weighed in, tweeting, "It's a ribbon that says you stand for people's rights, @krisjenner!"

Speculation was rife that Kris wasn't happy after the show, with Radar even claiming that she supposedly felt sabotaged.

How could we blame Amy Schumer for making a scene with Kim Kardashian and Kanye West and bringing some levity to an already somewhat awkward situation? As you may remember, the comedian took a dive in front of the famous couple on the red carpet at the TIME 100 gala back in 2015 — and West wasn't happy. Snaps from the event, seen above, show the "I Feel Pretty" star laying on the red carpet right in front of the duo, and the rapper stayed stone-faced as he led his then wife away from the comedian.

Schumer later opened up about what was going through her mind on "The Graham Norton Show" in June 2015, admitting she still thought it was all pretty hilarious. "I think falling is the funniest thing, so I just took a dive in front of them," she said. But that wasn't the first time she'd spoken about the incident. In May 2015, she also spoke about what actually went down on "Jimmy Kimmel Live!" She and Jimmy Kimmel admitted neither of them were the biggest fans of a red carpet, which is why she wanted to make things a bit more comfortable. "You feel like a girl at a party when a slightly hotter girl shows up behind you. It's like a guy who just wants you to die, 'Just die right now so I can talk to this hot girl'. That's how it felt," she shared.

This time we're throwing it back to September 2021 when Kim Kardashian and sister Kendall Jenner had their own awkward run-in at the Met Gala. As you may remember, Kim wore a well, very unique, outfit to the event in the form of an all-black ensemble that covered literally every inch of her body — including her face. All we could really see of the star was her long, dark ponytail, and this was actually designed by her estranged husband, Kanye West, according to Vogue. 

If you wanted even more proof of how restricting the outfit really was, though? Kim literally couldn't even see her own sister! Cue the serious awkwardness of a meme that went viral showing a pretty confused Kim struggling to identify her model sibling as well as several other hilarious takes on what people thought Kim could actually see under that now infamous outfit.

Kim later admitted via her Instagram Stories that the viral meme was pretty accurate, as she actually had no idea who it was who was trying to speak to her. "Kendall was calling my name and I couldn't see who it was but I saw the outline of her sparkly dress," she told fans, per People.

It looks like there's no love lost between Caitlyn Jenner and Lady Gaga — and an encounter at Elton John AIDS Foundation Oscar Party in March 2022 proved just that. The two had an awkward red carpet interaction that was caught on camera and (naturally!) went viral on social media with more than 2 million views as of April 8, 2022. In the clip, Caitlyn could be seen approaching the pop superstar before asking, "Are you spending time around Malibu anymore?" to which Gaga said, "Yes." Jenner then admitted that she hadn't seen the star around their local Starbucks anymore, to which a blunt Gaga hit back, "I've switched baristas" as she walked away. Seriously, we're still cringing!

Of course, this awkward as heck conversation inspired plenty of responses on social media. One person shared a screenshot of the "Paparazzi" hitmaker's seemingly disapproving glance as she walked away, writing, "That face gave us everything we needed to know about why nobody not even Gaga wants anything to do with Caitlyn Jenner." Others shared hilarious GIFs and memes of the extent Gaga may be going to avoid running into the reality star at the coffee chain.

Yeah, we're guessing Gaga won't be picking up her "Telephone" for this Olympian anytime soon.