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?

 

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.

 

“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!

 

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.

 

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?!

 

See many more photos at the Source: The TalkO

 

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