Caitlyn Jenner is a household name thanks to her connection with the Kardashians. When the Kardashian Klan first started getting famous, Cait had been married to Kris Jenner for over a decade, and together they had daughters Kylie and Kendall. The Olympic athlete was also a stepfather to Kris’ famous kids Kim, Khloe, Kourtney and Rob.
Back then, Caitlyn was known as Bruce. Rumours had been swirling for years that Bruce wanted to transition to a man, and it was just a few years ago that Cait introduced her new self to the world. Since then, she’s been living life as a woman and also hasn’t been on very good terms with the Kardashians.
Despite her feud with her family, Caitlyn continues to remain in the spotlight thanks to her interesting life. Check out these photos we’re sure she’d rather not have floating around on the Internet. Hey, we can’t always look picture-perfect in every photo! Which picture do you think is the most cringe-worthy?
15 She's Got Kim's Crying Face Down Pat
Barely anyone is cute when they cry, Caitlyn included. She was once caught on live television making this awkward crying face, which could totally compete with her step daughter Kim Kardashian’s infamous crying face.
The reality star’s eyes looked red and watery as she let the floor gates open. This close-up also leaves her skin looking leathery and tired. Plus, Cait’s lackluster makeup isn’t doing anything to help her look less washed out or to combat her wrinkles. Plus, someone needs to push that hair out of her face, pronto.
All in all, Caitlyn was looking pretty rough around the edges when this photo was snapped. Then again, she was clearly upset about something, so she probably didn’t give a care in the world about how cute she looked. And we can totally relate to that.
14 "Alterations" (And Photoshop) Have Done Her Wonders
It’s pretty clear that Caitlyn Jenner has gone under the knife multiple times since announcing her transition. Actually, rumour has it she was a regular at the plastic surgeon’s before coming clean about her gender identity. Aside from her boob job and surgery below the belt, one of the most notable things she’s had done is make her facial skin a heck of a lot smoother.
Before photos had Caitlyn looking closer to her age. She’s already 68, believe it or not! In this side-by-side photo, Cait’s skin looked a lot more wrinkly and leathery before she made her transition. But a few (dozen) trips to the Doc’s office to get a handful of Botox injections had smoothed out the reality star’s face. Now she looks just as youthful as the rest of the Kardashians. See, eternal youth can totally be bought!
13 When She Tried Stealing Kylie's Hairstyle
Sorry Cait, but this is not the right hairstyle for you! Caitlyn looked like she was trying to take a page out of Kylie’s book by rocking bright teal extensions. Kylie is known for being an avid wig lover, and trying out all kinds of crazy hair colours and cuts. Clearly her dad wanted to get in on the trend, but unfortunately Caitlyn just can’t pull this look off the same way Kylie can.
In this photo, it looks like Cait is trying too hard to be cool for her age. She looks great when her hair is styled and coloured, but not in this sort of unnatural ‘do. Luckily, Caitlyn knows what suits her best and she’s never hit the red carpet rocking a hair colour as bold as this. We prefer something a bit more natural and mature on her.
12 When Caitlyn Became Freddy Kruger
Yikes! Caitlyn looked like a character out of a scary movie when she debuted this nasty looking facial scar.
This photo was snapped when she was still living as Bruce. But rumours at the time said she was already undergoing facial surgery to make her features look more feminine, which resulted in the painful scar that required stitches to heal. Many people took this as proof that she was transitioning from a man to a woman, even though it was snapped in 2009- years before Cait would official come out!
“Bruce was going about his daily routine, getting his early-morning coffee at Starbucks, but he looked a little disturbed,” a source said about the photo when it was first published. “He was holding his head down and clearly tiring to hide this new mark on his face.” We can’t imagine how difficult it must have been for Cait to deal with all of the rumours and speculation.
11 Confidence Level: Selfie With No Makeup
Tons of celebs have been posting selfies with no makeup on, and we love the body-positive message this has been sending to the world. Caitlyn decided to hop on the bandwagon when she posted a video of herself talking to the camera with absolutely zero makeup on. The reality star was obviously feeling confident in her looks, but we’ve got to admit this isn’t her best look.
Caitlyn’s skin looked tired and blotchy, even though it appeared like she’d tried to blur out her imperfections with an editing app. Her hair was lifeless and slightly greasy, while her bathrobe made the video ultra casual. Like any of us, Caitlyn definitely looks more glamorous and awake with a touch of makeup. But she still looks ten times better than the average person while going makeup-free.
10 The Time She Had A Bit Too Much To Drink
We all thought Kris Jenner was the one in the family who liked to drink a bit too much. But it seems like Caitlyn has that exact same problem. The Internet was aflame when this cringey photo of Cait drinking a little bit too much made its way to the Internet.
The dad-of-six was photographed throwing her hands up in the air as she held on tightly to her alcoholic beverage. It looked like Cait was celebrating something and was trying to make a toast to the crowd that surrounded her. We must admit, that Caitlyn looked gorgeous sin her all-pin outfit. But it also looked like she needed someone to help her back to her seat.
The Kardashians have said they’ve made it a rule to never be intoxicated while in public, and this pic is proof that Cait should be living by that rule, too.
9 It Looks Like Old Age Has Caught Up To Her
Eek! Everyday looks like a bad hair day for Caitlyn as she’s been struggling with premature hair loss for years. Given that Cait was born a guy, it’s understandable and even to be expected that she might have thinning hair. Had she not begun hormone therapy when she did, she might already have a completely baldhead. Man, it really sucks to be a guy!
But the star proved she’s still struggling with hair loss when she was picture in this embarrassing moment. As the celeb bent down to get into her car, fans could see a balding patch of hair. We bet that Caitlyn already takes supplements in order to help her hair maintain its thickness. If that doesn’t work, then we suggest she take notes from her Kardashian relatives and start getting into either wigs or hair extensions.
8 Is That A Wig Or A Squirrel's Nest On Her Head?
Yup, Caitlyn has never ben known for having amazing hair! Before her transition, Caitlyn was spotted rocking this cringe-worthy hairstyle.
We can’t tell if she teased her hair too much in the back or is letting a woodland creature create a nest. But either way, this look just wasn’t working for her. The star’s hair was overly-voluminous on the top and looked like it was in need of a good brushing… and maybe a washing while she’s at it, too.
"People in the family have brought up his hair or his clothes, whatever it is and how absurd they think it is, but Bruce doesn't care, nor does he want to listen to any kind of criticism,” a source said at the time about Caitlyn’s frumpy style. “He thinks he looks great and cool and that's that." Hey, as long as Cait feels good, then that’s all that matters.
7 Transgender Isn't A Halloween Costume
Caitlyn would be horrified to see this photo because it’s so freaking expensive. During the Halloween after Caitlyn came out to the world, someone thought it would be a good idea to make a costume out of it. But someone coming out as LGBTQ+ isn’t a good idea for a costume! It’s straight-up offensive to trivialize such an important, courageous this as this.
Plus, the way the costume was designed was extra offensive. The costume was marketed towards men who wanted to dress up at Cait. Fans pointed out that this was like saying Caitlyn was simply still a guy dressed up in woman’s clothing, and failed to recognize the fact that she was transgender and was no a woman. This costume sparked so much controversy that it was eventually pulled from the online retailed. Good riddance!
6 This Super Cringey '80s Throwback
OMG! Can you believe this is what Caitlyn used to look like? Back in the ‘80s, Cait participated in a sketch video where she dressed up as a woman, complete with a cringe-worthy, badly permed wig. The video re-surfaced around the time that Cait transitioned from Bruce to her new self, and the media dubbed it as the first time the world got a look at female Cait, who wouldn’t come out for decades to come.
Caitlyn has admitted that she almost did come out as transgender in the ‘80s, but the fear of how the public would react kept her in the closet. Sources say that Cait went as far as to taking hormones to grow 36B breasts, but stopped shortly afterwards. Imagine what Cait’s life would have been like had she transitioned that early on. We bet she never would have married into the Kardashian family! What would the world be like without Kylie and Kendall?!
5 Everyone Has A Bad Angle Or Two Or Three
We’ve all had photos taken at god-awful angles, celebrities included. Caitlyn had an unfortunate run-in with the paparazzi when this ugly shot was taken. The reality star is featured giving the camera an unattractive grimace. It sort of looks like Cait smelt something yucky and this was the face she made.
At least the celeb was still looking like her usual glamorous self, other than the awkward facial expression. Caitlyn looked sophisticated in her white blazer, black top and silver jewelry. This look isn’t nearly as bad as some of the other frumpy get-ups the star has been photographed in over the years.
It’s easy to see that Caitlyn is still drop-dead gorgeous in this photo, despite the unflattering angle. Hey, we can’t always look amazing in photos, especially when they’re candid and you have 20 photographers chasing you at once, like it is in the case of Cait.
4 You Better Not Pout, You Better Not Cry
Here’s another instance where Caitlyn made an unflattering face at the wrong moment. We’re sure the star was looking fine otherwise, but this awkward candid shot makes her look like a duck out of water. Before she announced her transition, Caitlyn was photographed in this frumpy get-up and the media wasn’t too kind
It was easy to see that Cait was in the middle of her transition, given that her breasts were still visible in her slightly baggy top. The star’s baggy track pants and dated aviators didn’t help this cringey look. It also seemed like she’s recently gotten her lips plumped and her long hair was a dead giveaway that she was making some big changes.
Fans had speculated for decades before this that Cait wanted to live as a woman, so this outfit only fuelled the rumours.
3 That's Not Your Foundation Colour, Honey
We bet Caitlyn has had to learn a lot since deciding to live as a woman, including how to apply makeup. The celeb is always a stunner on the red carpet, thanks to her army of makeup artists and stylists. Caitlyn also isn’t half-bad at applying makeup to herself nowadays. Rumour has it her makeup mogul daughter Kylie has given her a pointer or two.
But there was a time when Caitlyn didn’t know what the heck she was doing when it came to makeup, like in this photo. The celeb is wearing a foundation colour that is way too light for her complexion, leaving her looking ghostly and washed out. Even more, her lipstick looked like it was applied carelessly as it was smudged out of the lines. Caitlyn’s unimpressed glares makes us thinks she knew this wasn’t her best look. Better take a trip to Sephora pronto!
2 How Was Cait Ever This Frumpy?
Caitlyn clearly didn’t feel comfortable in her own skin before publicly transitioning. We can see evidence of that in this picture, where the reality star looks absolutely miserable dressed in a frumpy guy’s outfit. Cait has proven that she has an amazing sense of style since debuting her new self on the red carpet. But she was obviously holding back from styling herself how she wanted when she was still living as Bruce.
In this photo, Cait flashes a grimace to the flashing cameras. She looks uncomfortable in her unmemorable outfit, which included a baggy plaid shirt, black track pants, and runners. This is so not the fashionable Cait we know and love today! Caitlyn has seemed so much happier since making her transition and dressing how she wants to. It’s hard to imagine that she was once this frumpy!
1 And She Just Keeps Smoking On
Tons of celebrities are known to light up on occasion. But that doesn’t mean their fans are any less disappointed or grossed out by it! Caitlyn was seen lighting a cigarette a few months back nonchalantly in front of the cameras. We’re sure she knows the health risks associated with smoking, but she didn’t seem to mind as she went about her business.
Caitlyn looked stylish in a simple black top and gold aviators. She kept her long hair down and styled in a chic ‘do. But unfortunately her smelly cigarette ruined this look. We’ve seen photos of Cait when her skin isn’t looking its best. Cigs contributed to premature wrinkles and can make your skin look tired or worn out. If the reality star wants to preserve her beauty, we suggest nixing this nasty habit altogether.