It’s been over a year since Kylie Jenner became a mother, and she’s definitely taken to her role well. From the looks of it, she’s been able to manage to raise Stormi alongside her booming cosmetics business, reality TV appearances, and all of the other work-related things the Kardashian-Jenner ladies do. Kylie took her 1-year-old along when her baby daddy Travis Scott went on tour, and she’s always seen traveling with Stormi for work. Needless to say, Kylie seems like she has this mom thing down pat.
However, it was only a few years ago that Kylie was making headlines for her questionable antics. Everything from the celebrity’s photoshoot choices to her relationship drama has been documented in the media. Fans aren’t afraid to call Kylie out when they think her behavior is out of line, and sources have given us plenty of juicy insight over the years. Needless to say, we bet there are plenty of things from Kylie’s past she wishes she could erase before her daughter is old enough to read the headlines. And we don’t blame her!
Keep reading to see photos that Kylie might wish she could delete so she can ensure Stormi doesn’t see them later on in life!
Kylie definitely didn’t think this photoshoot through!
Back in 2015, the makeup mogul received immense backlash on social media after posing in a wheelchair during an Interview magazine shoot. Many fans told Kylie that a wheelchair isn’t an accessory and shouldn’t be trivialized, so we doubt she’s too proud of these photos now.
"At Interview, we are proud of our tradition of working with great artists and empowering them to realize their distinct and often bold visions,” the magazine told E! News about the controversial shoot. “The Kylie Jenner cover by Steven Klein, which references the U.K. artist Allen Jones, is a part of this tradition, placing Kylie in a variety of positions of power and control and exploring her image as an object of vast media scrutiny."
Given that Kylie and her ex-boyfriend Tyga were together for over three years, there was a time that fans were certain he would be the father if she ever had a baby young. But alas, Kylie went on to have Stormi with Travis Scott, whom she began seeing only weeks after breaking up with Tyga.
Even though Kylie and Tyga have been over for years, there are still awkward photos like this one floating around online. Granted, they’re only awkward since we now know how things ended between the young lovers (and since Kylie’s brother now has a daughter with Tyga’s baby mama).
But, it’ll be even more awkward for Stormi as she grows up and sees these photos, knowing that Tyga was almost her dad.
Kylie isn’t letting motherhood cramp her style!
Mere weeks after welcoming her daughter Stormi, the reality star was shown partying it up on a yacht with friends, including her baby daddy Travis Scott and then-bestie Jordyn Woods. Given that the celebrity was only 20 years old at the time, many fans were surprised to see her enjoying certain beverages.
According to The Mirror, it was unclear if the couple’s newborn baby joined them on the boat trip. But what is clear is that Kylie hasn’t let being a mother stop her from enjoying her youth, even though she probably should’ve left some things until she was legal.
Back in 2013, Kylie and her sister Kendall caused quite the stir when photos surface of the then-teenagers partying hard. This photo shows the sisters hopping into their ride after a long night in quite a disheveled state, something we doubt Kylie wants her daughter to see considering she was underaged in the photo.
The girls’ mom Kris Jenner eventually commented on the controversy, explaining they’d attended the event with their (practically) brother-in-law, Scott Disick, and that no illegal activities had occurred.
"They thought it was a private party after the fashion show. They were told the club was rented out for the night,” Kris told E! News. "The girls don't have fake IDs and they don't [partake].”
It was only a few seasons ago on Keeping Up With the Kardashians that Kylie was still with her long-time boyfriend Tyga. The reality show documented the couple’s highs and lows, including this scene in which Kylie is shown tearfully breaking down about things in front of her sisters.
“Did you guys get in a fight?” Kourtney was shown asking Kylie, to which the makeup mogul replied by saying she and Tyga had called it quits.
Given that Kylie and Tyga have long been over, we bet she only finds scenes like this embarrassing. And she probably hopes the day never comes that her daughter sees her crying over her ex!
One of the most embarrassing moments Kylie has had on social media was when she accidentally spilled her beverage on herself while in the car… and it totally looked like she had wet herself! Fans couldn’t understand why the then-teenager posted videos of her and her friends laughing about the mess, as no one could tell what really happened.
"Why does this always happen to me?! " Kylie could be heard asking in one of the videos, E! News reported. "I always spill my [beverage]." The celebrity then proceeded to ask, “Does it look fine?” to which her friends replied, “Yeah, you look good! It’s fine!” Looking back, Kylie probably only now realizes how eyebrow-raising the whole scene was.
No one was surprised when Kylie went all-out for her 21st birthday. But we can honestly say we weren’t expecting the cake that she chose!
The new mom celebrated her big milestone in style last year with a Barbie-themed soiree. The celebrity and her then-best friend rocked matching, sparkly pink dresses, while the whole venue was decorated in pink. However, it was Kylie’s birthday cake that really had everyone talking.
The controversial confection featured an array of Barbies positioned to look like they were sick from a night out. One Barbie was face down in a toilet, while another was holding a mini bottle. We guess Kylie wanted everyone to know that she was legal and ready to mingle!
Kylie and Travis have made it extremely clear just how into each other they are. They’ve never been afraid to hold back their public displays of affection, even when the cameras on looking on.
There have been tons of photos showing the young couple affectionately kissing each other or Travis grabbing his girlfriend. As cute as this photo is, we doubt Stormi wants to grow up seeing photos of her parents getting close - and Kylie probably feels the same way!
Need more evidence that Kylie and Travis are all over each other? The makeup mogul recently said social media she’s ready for more babies with him. In honor of his birthday, she wrote, “Let’s [mess] around and have another baby.”
There have been plenty of times Kylie has angered fans for her choice of photoshoot, and this was one of them. In 2015, the celebrity received backlash for appearing to sport blackface in a series of photos taken for her social media pages.
Many fans said the dark makeup was not appropriate. But it wasn't only fans who reacted. Kylie’s photos even prompted some fellow celebs to speak up, including Zendaya. “At first, I saw more of an avatar look but thank y'all for keeping me on point....we all gotta stay aware of what image we project #lessons,” the actress wrote over social media.
The backlash prompted Kylie to explain the makeup was a result of special effects. "This is a black light and neon lights people," she wrote online. "Let's all calm down."
It’s not hard to believe that Kylie partied and partook underage before she became legal, considering the social circle she was raised in. Plus, there have been plenty of photos published proving the celeb likes to get wild, including ones she posted herself.
In this picture, the then-underage star was shown goofing around with pals while holding a bottle that looked suspicious. While it's unclear if she was actually flaunting a certain beverage (or if it was something else), it definitely painted Kylie in a poor light.
Despite the photographic evidence, in 2017, a 20-year-old Kylie insisted she’d never had a bev before. “I feel like that's fun. You know, I've never had a [beverage] before so I just wanna know what it's like,” she said on KUWTK about looking forward to turning 21.
There have been various times the Kardashian sisters have been called out for cultural approbation; Kylie included. This family seems to love rocking cornrows and other hairstyles traditionally associated with black culture, without acknowledging where they got their inspiration. So, this hasn’t sat well with fans.
When Kylie posted a mirror selfie featuring herself rocking cornrows, it caught the attention of Hunger Games actress Amandla Stenberg. “When u appropriate black features and culture but fail to use ur position of power to help black [people] by directing attention towards ur wigs instead of police brutality or racism #whitegirlsdoitbetter,” Amandla wrote online in response.
Kylie’s reaction to Amandla’s comments didn’t help the situation, as she wrote, “Mad if I don’t, Mad if I do … Go hang w Jaden [Smith] or something.”
Kylie dated her fair share of famous men before finding love with Travis Scott. One of her earliest relationships was with Will Smith’s son Jayden. However, not even that relationship ended without its fair share of drama.
When Kylie uploaded this photo featuring herself and a shirtless Jayden in bed in 2014, the starlet immediately began facing backlash. Since Kylie was only 15 years old at the time, many fans suggested that the photo was inappropriate and Kris should be more concerned about what her then-teenager posted to social media.
Now that she’s a mom, we doubt Kylie would want Stormi posting selfies in bed with guys, even if they were just friends. So this is one photo she likely wishes she never uploaded.
We know that the Kardashians love their money - why do you think they do so many sponsored posts? But many fans weren’t feeling it when Kylie posted this photo showing off just how much her family loves their moulah.
In the photo, Kylie and her sister Kourtney were helping Kourtney blow out the candles on her birthday cake. However, it was the fact that Kourtney’s head was incorporated into a $100 bill on the cake that didn’t sit well with most fans. “We get it, you’re super rich, calm down,” one fan wrote via social media.
Since then, Kylie has also received backlash for calling herself a self-made millionaire. We bet she’s going to want to keep these sorts of things to herself and away from Stormi’s eyes and ears.
Kylie and her sister Kendall found themselves in the middle of a controversy in 2017 when they released a line of t-shirts without the proper licensing.
The controversial graphics tees, which cost $125 each, featured the socialite’s faces overtop of big musical legends, including Tupac, the Notorious B.I.G., and Ozzy Osbourne. However, almost as quickly as the girls put the shirts online for sale, they were pulled down after social media users went ablaze. According to The Guardian, Kylie and Kendall’s legal team also received threats from the estates of some of the icon’s whose faces they’d used.
The controversy even caught the attention of celebs. Sharon Osbourne wrote online, “Girls, you haven’t earned the right to put your face with musical icons. Stick to what you know … lip gloss.”
Despite owning quite the collection of designer cars, Kylie hasn’t had much luck on the road. She’s made headlines for being involved in numerous accidents.
For instance, only two weeks after getting her license, 16-year-old Kylie caused a three-car collision, People reports. Luckily, no one was hurt. Then, Kylie was gifted a $320,000 Ferrari for her 18th birthday by her then-boyfriend Tyga. However, only weeks after receiving it, the star got into a crash that left the car beyond repair.
On top of all that, the magazine adds that she’s also been in trouble for speeding and illegal U-turns! So, it’s likely she’s now hired a chauffeur to tote her and Stormi around rather than relying on her own driving skills (or lack thereof, we should say).
Based on this picture, the photoshoot Travis and Kylie did for GQ seems pretty harmless, right? Well, fans definitely disagree.
The power couple, who was described by the magazine as “a billionaire business mogul" and “the most electric rapper in the game,” posed for their first magazine cover together last year. But many fans took issue with the fact that Travis was completely clothed, while Kylie was wearing next to nothing in some of them.
“Funny how the guy is all dressed up and the lady is unclad,” one social media user wrote. Another said, “Wouldn’t it make more sense (for artistic purposes, of course) if @trvisXX was also mostly [bare]?” Given the double standards that fans pointed out, we’re not sure how proud Kylie would be to show these photos to her daughter.
The Internet was not having it when photos of Kylie, Kendall, and Kim were published showing the sisters texting during a moment of silence at the 2014 VMAs.
The crowd had been asked to bow their heads in silence to honor the events in Ferguson, Missouri, so fans were astounded the celebrities seemed to ignore the simple request so blatantly.
However, the family has since insisted the photos were taken out of context. "I just specifically remember not texting and bowing my head down for the moment of silence and that's all I have to say about that," Kendall Jenner told Huffington Post about the situation. Still, the photos do speak for themselves!
It’s the thought that counts? Well, if that’s true, then we have no idea what Kylie was thinking when she purchased this cake for her friend Jordyn Woods’ birthday.
Back in 2015, the celebrity surprised her then-bestie with a cake featuring a word NOT considered okay. Considering Jordyn's background, many fans thought she’d be offended by the controversial cake. But evidently, she wasn’t, since both girls posted photos of the confection to social media without thinking about the backlash. However, fans made sure to let Kylie know just how distasteful they thought the cake was.
Needless to say, we bet Kylie hopes her daughter never discovers this photo online.
For the most part, Kylie and her family are extremely careful about what the cameras catch them doing (they have momager Kris to thank for that!). But there have been a few moments - like this one - in which the sisters have been caught in uncomfortable positions.
In this photo, Kylie was seen losing her balance while attending a Hollywood event. While it’s unclear if she had too much or was just having trouble with her shoes, we’ve got to admit this is a pretty compromising angle.
“She’s never home before daylight and it’s not unusual for her to throw ragers that last for three days,” a source told OK! Magazine about Kylie’s partying several years ago.
Now that Kylie is a mom, we bet she wants to promote a healthy body image for her little girl. But give all of the times the makeup mogul has used photoshop to alter her appearance, it might be tough convincing Stormi that she believes going natural (or at least filter-free) is better.
Back in 2016, the celebrity received flack after she posted this picture of her advertising Fashion Nova jeans. However, fans couldn’t help but point out that her behind look bigger than usual, causing them to call her out for editing her pictures.
Of the controversial picture, Elle Magazine explained, “Just look at the center belt loop on her jeans versus the one on the pants shown on the site. Kylie's is a little too long to be only natural enhancement.”
Sources: E! News, The Mirror UK, Cosmopolitan, Us Weekly, People Magazine, GQ, Elle Magazine, Hollywood Life, Huffington Post.