50 Adorably Awk Pics of Kendall and Kylie

Kendall and Kylie Jenner

Jesse GrantGetty Images

As anyone who watches Hulu keeping up with kardashian Knows, Kendall Jenner and Kylie Jenner are probably the most private members of the Kardashian family at the moment. Yes, they do appear on the show from time to time, but they don’t talk about their personal lives, we don’t see their relationships on screen, and they keep things too simple—usually to react. Let’s just pop up for someone else’s drama. All of which may have something to do with the fact that these two literally grew up in the limelight when the Kardashians entered the wild world of reality television when they were just kids.

As Kendall put it during Kuwait Reunion, “No offense to my older sisters, but I think Kylie and I especially have had the opportunity to see our older sisters go through marriages and relationships and breakups and see them in public. It really is I had a personal preference. Younger age. … I think it makes my life a lot easier and our relationship a lot better, to be honest. I feel like it’s a personal matter and someone else’s And for there is no justice or knowing.”

In addition to spending their childhood with cameras in their home 24/7, Kendall and Kylie have been attending events since they were little kids, and the result? The two of them had countless awkward moments on the red carpet in a series of truly random events. Like, imagine having cameras for all of your most coveted middle school outfits, because we’re here doing so much!

1 50. of

2007

In 2007, Kendall and Kylie looked like two cute little angels.

2 50. of

2007

Coordinating in pink and zebra-print outfits is never a bad call.

3 50. of

2007

I might never get over this picture.

4 50. of

2007

This is what you’ll find if you look up “healthier” in the dictionary.

5 50. of

2008

There’s some incredible fashion happening here (looking at you, Khloe’s bootleg jeans).

6 50. of

2009

Less so with braces and bangs!

7 50. of

2009

Anyone else remember coordinating your braces color to various holiday moods?

8 50. of

2009

Someone explain why this red carpet was literally grass.

9 50. of

2010

I am pretty sure I have this exact tank top.

10 50. of

2010

The Teen Choice Awards were the venue for 2010. or something else. So I listen.

1 1 50. of

2010

Back when Rob still walked the red carpet!

12 50. of

2010

Exactly how many premieres did Kris Jenner force these poor girls to attend?

13 50. of

2010

Pictured here: Kendall, Khloe and Kylie at the premiere of the Oscar-winning film burlesque,

14 50. of

2011

If you weren’t posing with a candy necklace in 2011, what were you doing?

15 50. of

2011

The Kardashian collection at Sears was an iconic chapter in American history.

17 50. of

2011

Try it in what it calls coordinating Forever 21 Hello Kitty apparel.

18 50. of

2011

Their matching hands, meep < 3.

19 50. of

2011

Kendall’s body language in this picture = me all the time.

20 50. of

2011

My biggest conclusion from this picture is honestly that Khloe looks amazing with orange hair.

21 50. of

2011

They loved the color coordinating their fits!

22 50. of

2011

Looking at these photos, I think Kendall and Kylie should only be bringing each other to the red carpet event from now on.

23 50. of

2011

“Stand next to each other, but lean as far away from each other as humanly possible.”

24 50. of

2011

“NATURAL LOOK!!!!” – Photographer, probably.

25 50. of

2011

Not really clear why they’re holding on to these things, but ok.

27 50. of

2011

how lovely! so innocent! So unaware of what was to come (billions of dollars).

29 50. of

2011

IDK what a “Kardashian khos” is but I’m concerned.

30 50. of

2012

This was the era when Kris Jenner kept showing them off at movie premieres.

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