Kristin Cavallari's Unfiltered Beauty Evolution Will Take You Back

Photo: Jason Merritt/FilmMagic.
Kristin Cavallari would like to get something off her chest. And, if you watched Laguna Beach religiously like we did, you probably already know what it is: She doesn't give a damn what you think.

We sat down with the unfiltered star at a Young Living Essential Oils event (she's collaborating with the brand for the holidays) and asked her to go through every beauty look since she catapulted into the spotlight at age 17. With 19 throwback photos in hand, we fully expected a little hesitation. But Cavallari held nothing back. In fact, each time she'd cringe at an image — or murmur her signature "Oh, god!" — we'd gently offer, "We don't have to use that one if you hate it that much." Her response, of course, was spot-on. "Oh no, I don't care if you do. I really don't."

Throughout our conversation, one thing became clear: With Cavallari, what you see is what you get. She isn't afraid to speak her mind, without apology or recourse. So, whether it's dishing on fake-tanner fails or her worst hair-color moments, you'll feel like you're back in your living room, watching her on TV, reliving the entire thing all over again.
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Photo: Jason Merritt/FilmMagic.
MTV Laguna Beach Cast Portraits, 2002
"Oh god, what was I thinking here? I didn't know any better. This is one of the first photos I ever took before we started filming for Laguna Beach. I was 17, and I thought I looked really good. My eyebrows are so thin. I look very puffy and bloated. And I thought my blue blazer was everything."
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Photo: Jon Kopaloff/FilmMagic.
Us Weekly's Young Hollywood Hot 20, 2005
"I look like a little girl. I went through a phase where I didn't really know my style, and I didn't have enough confidence to say, 'I don't really like that.' So I said 'yes' to everything because that was the stage in my life. I also probably did my own hair here. I don't know [what hairstylist] would put two bobby pins in it."
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Photo: Chad Buchanan/Patrick McMullan/Getty Images.
2nd Annual Celebrity Rock'N Bowl, 2006
"I look so tired! I definitely did my own hair and makeup here. I really thought I had it going on, that's for sure. But I probably should have just gone home to sleep."
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Photo: Jon Kopaloff/FilmMagic.
The Lake House Movie Premiere, 2006
"This is the first time in my life that I cut my hair this short, and I love it. I got it styled and I remember thinking, God, I love my haircut, and then I could never make it look this good on my own. [laughs.] So that was unfortunate. I also got my makeup done for this premiere and I still use the makeup artist today, Karan Mitchell. She's the best. This is, to this day, one of my favorite looks."
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Photo: Chris Polk/FilmMagic.
MTV Australia Video Music Awards, 2007
"This is aggressive," Cavallari says, bursting out laughing. "My hair is yellow! There's a lot of liner going on and my hair is yellow. I like the top. But wow, that makeup."
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Photo: Steve Granitz/WireImage.
Eagle Eye Movie Premiere, 2008
"I did my own makeup, and this is what I typically look like...more natural."
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Photo: Alexandra Wyman/WireImage.
Nylon + YouTube Young Hollywood Party, 2010
"We were filming The Hills, and [on the show] I always did my own hair and makeup, so I looked like a normal human being. But for this, we were actually filming for an event, so I got my hair and makeup done. And I look...not like what I usually looked like every day. So, in that way, it was a bit of a drastic change. But this is fun. I don't know if I would do this hairstyle now — but I'm glad I did it [then]."
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Photo: Gregg DeGuire/FilmMagic.
Salt Movie Premiere, 2010
"Oh no...this. I hate this. This is maybe the picture I hate the most out of anything I've ever done. I actually had my hair done, but I didn't like it, so what did I do? I took it out and put bobby pins in it. My dress was hideous. The entire look is bad."
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Photo: Jason LaVeris.
BlackBerry Torch Launch Party, 2010
"This is actually right when I met [husband] Jay [Cutler], because I met him when my hair was a little darker. The dark was fun, but I do like myself better blond. [Cutler] likes me better blond, [too]."
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Photo: Gregg DeGuire/FilmMagic.
Burlesque Movie Premiere, 2010
"I think I have green eyeliner on, which is a very interesting choice. [laughs.] It actually matches the dress I wore that night, which was the doing of my makeup artist — I can't take credit for it being monochromatic. But I'm into it.

"I remember Will Ferrell came up to me at that event, and I had never met him before, and he started taking photos with me. And I was like, What is happening right now? But it was an awesome moment, so I decided to go with it. You know, I thought, My hair is on-point; my green eyeliner is good... I'm ready for anything."
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Photo: Paul Morigi/WireImage.
New York Fashion Week, Spring 2011
"I got talked into a red lip, and I don't hate it. But I'm such a nude girl when it comes to lipstick. I think [red] makes me look a bit pale. My hair is still darker. I think the red would have looked better if I had more of a tan, and my hair was blond."
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Photo: Jason LaVeris/ Getty Images.
Comedy Central Roast Of Charlie Sheen, 2011
"My makeup is very natural here; I don't think I'm wearing very much of it at all — I could probably use a little more. Just kidding. No, I'm not mad at this. I'd still wear my hair like this today."
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Photo: Jason Merritt/Getty Images.
Super Mario 3D Land Launch, 2011
"The fishtail is cute. I kind of wish I tucked back a few more pieces — it looks like I just rolled out of bed — but it's cute...if I was 18. But I'm definitely not 18 in this picture, am I?"
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Photo: Ray Tamarra/Getty Images.
New York Fashion Week, 2012
"Marcus [Francis], my hairstylist at the time, put braids in it. At the time, I sort of let him do whatever he envisioned. And I like the hair. I love throwing a braid into a simple pony or bun; I think it just adds another element to it."
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Photo: Shahar Azran/FilmMagic.
FFANY Shoes On Sale Gala Fundraiser, 2012
"See, this is why I stick to nudes! No, I'm kidding. I was going for '80s Hollywood glam, but I probably wouldn't have worn the ['70s] dress. I have a lot of different eras going on in one picture.

"But one thing: You can totally tell the difference in my brows here compared to the [photo] before this. Filling in your brows makes such a difference; it really does."
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Photo: JB Lacroix/WireImage.
Ubisoft Game Just Dance, 2014
"I was pregnant with Jaxon in this picture, actually. I like this. I like the slicked-back, straight-haired ponytail. For a simple pony like this, it's nice to do a dramatic eye. Karan [Mitchell] did my makeup here; again, she's so good."
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Photo: Gregg DeGuire/WireImage.
NBC Universal Summer Press Day, 2014
"Oh, wow. I think I was about four weeks out from having [Jaxon] in this picture. This was exciting because I was promoting The Fabulist on E!, a show I hosted for about a minute.

"I was after the whole boho thing. Scotty Cunha did my hair here, and he added a few small braids. I'm wearing minimal makeup. It's just a sweet, soft look."
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Photo: Mike Pont/WireImage.
Bella Cover Launch Party, 2016
"This was during a press tour for my book, so this was a really exciting time in my life. I like a good topknot, and I like my makeup here. Karan Mitchell, again, best makeup artist on the planet, I swear. I love this whole look; I would do it again."
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Photo: Steve Granitz/WireImage.
Carousel Of Hope Ball, 2016
"This is one of my favorite red-carpet moments. Justin Anderson colored my hair the day before, and going this blond was not my intention. I don't know why it looked so light, but the next day it did not look that. Maybe it was because the color was so fresh. Also, I must have done a fake tanner in this photo, because I look incredibly tan.

"But I loved this dress. It's not often I get to go to an event and wear a gown, so it was really fun. This was just a night where everything came together. It was fun; I was out supporting juvenile diabetes. My husband has type-1 diabetes, so the cause is near and dear to my heart. So all around, great night."
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