1. The Early Days of Kris and Caitlyn
Kris Jenner married the person we now know as Caitlyn Jenner in April 1991. This was just one month after her divorce from Robert Kardashian, with who she remained close friends with.In this rare picture, we can see Kris and Caitlyn (who was then known as Bruce Jenner) in the early days of their marriage. They would later have two daughters together: Kendall and Kylie. Seeing photos like these are even stranger knowing that Bruce would transition in 2015, becoming Caitlyn Jenner.
(Image/ Source: RadarOnline)2. Kris and Paris Hilton
Kris' daughter Kim Kardashian had her first taste of socialite life as Paris Hilton's assistant. It seems crazy to us now, but yes - once upon a time, Kim was just a personal assistant!
Here, Kim's mother parties with the ubiquitous Paris Hilton. We know that Kris has always been a cheerleader for her children, and it's clear that she loved that Kim was making friends with famous faces like Paris.
(Image/ Source: People)3. The Party Mom
As well as being a savvy businesswoman (she started the careers of all her children, so she must have some skills), Kris doesn't hide the fact that she loves to party, too. We've all seen her drink a vodka or two, or three, on Keeping Up with the Kardashians.
Sometimes, though, the partying takes it out of Kris, as we can see in this never-before-seen photo. It's alright Kris - we've all felt the same thing at the end of a long night partying... Some of us don't have a driver to take us home though!
(Image/ Source: Dailymail)4. Kris On the Cusp of Motherhood
This picture was taken just before Kris gave birth to her first daughter, Kourtney - she's clearly about to pop! We now know that this was just the beginning of Kris' mom journey, as she would have five more kids.
Now, Kris is more focused on her grandchildren - she now has ten! We bet Kris had no idea when this picture was taken that some of her kids and grandkids would grow up to be some of the most famous people on the planet.
(Image/ Source: Dailymail)5. A Candid Kris Jenner
It's rare that we get a non-posed, candid picture of Kris, but that's exactly what this one is. With glowy skin and her hair tied back, it's clear that Kris was just feeling herself when she took this.
The revealing bikini also gives us a look at her incredible body. Kris was 63 when this was taken, but she doesn't look a day over 40! This is even more amazing when you think that Kris has had six kids at this point.
(Image/ Source: Mirror)6. Kris as a Vogue Model?
Wait, is that Kris Jenner? We thought it was Kendall for a second! It's incredible how alike mother and daughter look - this shot could easily be one of Kendall's Vogue shoots.
This very early modelling shot of Kris showcases a more natural look that we're now unused to seeing considering the various surgeries all the Kardashian and Jenner kids have had done. They're all beautiful, but we especially love this windswept, easy-going look that Kris has here.
(Image/ Source: Dailymail)7. Did You Know She Smoked?
This quick snap of Kris showcases the matriarch in her full party mode. With a drink in hand and a cigarette in the other, she's clearly not thinking about work at this moment!
Did you know that Kris smoked? Rumour has it that she's trying to quit and only has an occasional drag now, but she used to smoke a lot more. In this picture, she's even taken her habit indoors.
(Image/ Source: Dailymail)8. A Very Young Kris
It's very rare that you see a childhood photo of a celebrity - especially one with as much star power as Kris Jenner. However, this rare snap shows a young Kris, perhaps just out of high school or college.
Compared to her shorter look now, Kris clearly used to favour long locks - just like her daughters. In fact, in this photo, you'd be forgiven for thinking that this was actually a young photo of Kourtney as the two look so much alike!
(Image/ Source: Pinterest)9. Kris and Robert Kardashian
We can't get over how adorable this photo is. Kim and Robert pose outside their beautiful house, and can you guess who they are holding?
Well, the older child is Kourtney, who must look back on this bowl cut with horror now! On the other side, Kris is holding a very young Kim Kardashian. The two parents are positively glowing with happiness!
(Image/ Source: Instagram @kimkardashian)
10. Kris on the Red Carpet
Kris Jenner has always been glamorous, like this red carpet shot shows. The photo was taken on December 10th, 1990, and you can see Kris transitioning from 1980s style to a more laidback 1990s outfit.
Sporting her now iconic short haircut, Kris also shows that she's got an eye for putting together a chic outfit. We know where Kim got her styling skills from!
(Image/ Source: cosmopolitan.com)11. Kris Being the Perfect Mother
Kris has always put her children first, and in this photo, we can see a younger Kris dropping her daughter off at school. But can you tell which of the Kardashian children this is?
Actually, this is a very young Khloé Kardashian! Could you tell from the beautiful curly locks? Kris is also demonstrating that she can be the most stylish mother around - we love her laidback blouse and plaid shorts outfit.
(Image/ Source: Instagram @khloekardashian)11. Questionable Fashion Choices?
We know that Kris has some outstanding fashion skills, with the ability to put together a beautiful and relaxed outfit at the drop of a hat. However, that's not exactly what's happened here..!
This very dated photograph of Kris shows her in some very era-specific fashion. However, she still looks gorgeous, and we're sure that that glossy lipstick has come back in fashion now!
(Image/ Source: Instagram @kimkardashian)12. Robert and Kris in the Early Days
Kris married Robert Kardashian in 1978, and we guess this photo must have been taken not long after their first child, Kourtney was born in 1979. It's clear that Kris is loving being a mom - though Kourtney doesn't look so pleased!
Can we also mention Kris' incredible fashion choices? The matching yellow hat and dress is a bold choice but perfectly matches Kris' tanned skin - we even love those aviator sunglasses that Robert has chosen!
(Image/ Source: Instagram @kourtneykardashian)13. Kris with Bangs
Have you ever seen a picture of Kris Jenner with bangs? Well, now's your chance. This rare picture shows Kris with her cousin, Cici Bussey, sporting some very stylish bangs.
It's incredible how much of her daughters you can see in Kris in this photo. In her early days of stardom, Kim Kardashian also flaunted bangs, and we think we know where she got the idea from.
(Image/ Source: people.com)14. Pretty in Pink
Recognise the blonde woman here? Yep, that's Kris' cousin Cici again! Here, Kris and Cici pose with a very young Kourtney Kardashian.
The matching outfits lead us to believe that this could be a wedding or other occasion, but maybe the Kardashian family just love wearing the same colour? A moment of appreciation for Kris' perm - it's certainly very 1980s.
(Image/ Source: people.com)15. Kris and Robert Being Party People
If you didn't already know that Kris Jenner is the life of the party, this photo will finally prove it to you. She's looking absolutely gorgeous in white and is clearly the center of attention at this party.
Also, once again, we can clearly see where the Kardashian and Jenner girls have got their good looks from. Kris looks as good then as she does now, and is proving that it is possible to look good in white.
(Image/ Source: people.com)16. A Very Sporty Kris
It's rare that we see Kris wearing anything that isn't entirely glamorous, but here she proves that she can also do the athleisure trend - before it was even trendy!
Nowadays, we doubt you'd see Kris in a hoodie and a cardigan, but she's really pulling it off here. But we just can't see Kim trying the same style.
(Image/ Source: people.com)17. A Family Affair
It's rare nowadays that you see a picture with the entire Kardashian clan together, including a very young Kourtney, Kim, Khloé, and Rob.
This is a real throwback - did you even recognise Khloé on the left there? Everyone here has definitely transformed in the last 20 years, not least with their style. However, they're all still recognisably the Kardashians.
(Image/ Source: people.com)18. Kris Getting Older
Kris definitely isn't the star of this photo, as we can't take our eyes off an adorable childhood Kendall Jenner! Both of the Jenners look fabulous, though.
Here, you can tell that Kris is growing into her matriarch style, with that perfectly coiffeured short haircut and pristine eyebrows. Kendall, on the other hand, looks very cute with bangs - could it be time for her to bring them back?
(Image/ Source: people.com)19. Kris and Her Youngest Child
In this photo, Kylie Jenner can't be much older than one year old, and here mother and daughter are celebrating a birthday at their home.
Kris was 42 when she had Kylie, making her perhaps just a couple of years older at this point. However, she still looks incredible, with those classic Kris eyebrows and a light dusting of makeup.
(Image/ Source: Instagram @krisjenner)20. Halloween Kris Jenner
Did you know that Kris Jenner loves to get dressed up? Here she is with a little Kendall and Kylie in matching pirate-themed costumes for Halloween.
It's possible that Kris still celebrates Halloween now with her young grandkids. But this photo is really apt when you consider Kris' role as captain of the Kardashian gang - I'm sure she's always ready to defend her crew with a metaphorical sword.
(Image/ Source: Instagram @krisjenner)21. Another Halloween Picture
Yep, we have more proof that Kris was a big fan of Halloween in the Kardashian household. It's unclear who's in this picture - though we reckon it's a young Kourtney and Khloé.
It's unclear if Kris has dressed up for this Halloween party, but her daughters look adorable in their Disney-style outfits.
(Image/ Source: people.com)22. Kris and Her Eldest
Kris and Kourtney have a very special relationship, seeing as she is Kris' first child. In this sweet image from Kourtney's childhood, mother and daughter alike have dressed up as kittens.
But something that's even more dramatic in this photo than the cat makeup is Kris' choice of hair-do. The Kardashian matriarch has swapped her traditional sleek short style for a very voluminous cut that goes almost to her shoulders.
(Image/ Source: hellomagazine.com)23. Kris and the Jenners
This photo was presumably taken in the early 00s - hence Kris' very on-trend sunglasses. She and Caitlyn look understandably happy with their handiwork with the Jenners' costumes - Kendall and Kylie look picture-perfect as Dorothy from
The Wizard of Oz.
Of course, Kendall and Kylie had to be matching. There are just two years between the Jenner sisters, and what mom wouldn't want to see their daughters in adorable tiny outfits?
(Image/ Source: people.com)24. At the Salon
Oh no! This still from Keeping Up with the Kardashians is a photo that Kris might not want people to see. In a rare non-posed pic, Kris looks like she's getting her hair refreshed.
However, considering the Kardashian matriarch is over 60 years old, we think she looks incredible. Despite her skin not looking its best, we can't spot a single wrinkle!
(Image/ Source: lifeandstylemag.com)25. Kris and Kourtney Close-Up
We have more proof that Kris actually did have bangs at some point in the 1980s. Here, she poses with her eldest daughter Kourtney.
While Kris looks directly into the camera, Kourtney is just a little distracted by something out of shot. Could her father be standing there?
(Image/ Source: Instagram @krisjenner)26. A Skiing Trip
Like any American family in the 1980s, the Kardashians loved a good skiing trip. In this photo, the whole gang - Kris, Kourtney, and Kim - are fitted out in appropriate attire as they prepare for a day on the slopes.
While the young girls are styled in ice blue ski suits, Kris has decided to show her unique and flamboyant style. Instead of going for a basic ski suit, she opts for a deep green with pink accents. Go Kris!
(Image/ Source: Instagram @krisjenner)27. Unrecognisable Kris
While Kris is almost always recognisable thanks to her good look, we had to do a double-take when we saw this photo. With her shoulder-length hair and bangs, she definitely doesn't look like the Kris Jenner we know now.
Kris posted this photo for Kim Kardashian's birthday, where she praised her for being the "most loving mommy and wife, incredible businesswoman and loyal friend." Aw!
(Image/ Source: Instagram @krisjenner)28. Businesswomen of the 1980s
Throughout this picture gallery, we've seen the Kris can do red carpet glam, children's birthday party, and Halloween/costume party excellence. But here she is demonstrating that she can also do fierce businesswoman style.
This photo was taken at Kris' 33rd birthday party, and she poses with her cousin Celeste and friend Shelli. They are all really pulling off 1980s bangs, as well as powerful pants suits - Kris is actually wearing Thierry Mugler.
(Image/ Source: Instagram @krisjenner)29. Family Portrait
We just adore photos of the entire Kardashian clan - it's amazing to see Kourtney, Kim, and Khloé as youngsters. This photo is especially amazing as we get a glimpse of Kris in true matriarch mode.
She is truly the center of attention in this photo, and while her children have been styled with voluminous locks, Kris has kept it more simple. Opting for a sleek look - with not a bang out of place, we must say - she looks exactly the part.
(Image/ Source: Instagram @krisjenner)30. The Start of the Kardashians
This image truly captures the Kardashian family as we may have seen them at the beginning of Keeping Up with the Kardashians. It's also obvious that everyone has been influenced by the 00s pop-rock style - is that an untied tie around Kris' neck?
Kris looks completely comfortable with the state of her family affairs and ready to take the next step to complete global stardom. She's also debuting a very on-trend, layered bob cut which we love.
(Image/ Source: Instagram @krisjenner)