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Kristin Cavallari on her first red carpet looks: 'I'm still mad about this one'

The “Very Cavallari” star looks back on some of her most memorable fashion looks with TODAY Style.
/ Source: TODAY

Kristin Cavallari has been in the spotlight since the early 2000s with her hit reality shows “Laguna Beach” and "The Hills." She's since become a TV personality, fashion designer, author and mom of three. The “Very Cavallari” star looks back on some of her most memorable fashion looks with TODAY Style and reveals what she (and husband Jay Cutler) think of her current style.

Kristin Cavallari, hair, throwback, style, fashion
Cavallari said this visit to "The Late Show with David Letterman" was one of first big events. "I was so nervous, I actually took a tequila shot right before I went on, because I didn't think I would be able to do it — even though I was 18."FilmMagic

"The thing that I noticed here more than anything is my hair," said the 32-year-old. "My hair is a little too poufy on top there, but, you know, I think I was 18 here, so I think for an 18-year-old, I look all right, I guess. That pattern on that dress — I would never wear today. But it could be worse."

Kristin Cavallari, TRL, style, fashion, "Laguna Beach"
Cavallari visited MTV's "TRL" on July 25, 2005.WireImage

"This is pre-stylist," Cavallari said. "This is all me — fresh out of 'Laguna Beach,' jean skirt and all. I didn't take that jean skirt off for, like, two years and the bangles. I mean, I feel like this was very true to that time period though ... Just a regular high school girl, you know?"

Kristin Cavallari, style, fashion, VH! Big in '05 Awards, curly hair
Cavallari called this her "ice skating dress." (As seen with "Laguna Beach" costar Lauren Conrad.)WireImage

"I was nominated this night (for VH1's 'Big in '05 Awards') so this was a big night for me," she said. "This looks like an ice skater dress, though. This was not a good moment. The hair is extremely curly, my eye shadow matches my dress. There's just a lot happening."

Kristin Cavallari, young, style, fashion, jeans, straight hair
The official uniform of an early aughts girl.FilmMagic

"You guys really went to the archives. I'm like 10 pounds heavier," said Cavallari. "This was my first red carpet — like, the first red carpet that I walked — and this was a massive red carpet. So, I remember stepping out and being like, 'Oh my God, this is so crazy.' I was so nervous.

"Again, styled by yours truly, which is good that finally I found a stylist. But, you know, the flare jeans and the whatever this kind of top is. This was all me. (I) could've used a hairstylist and makeup artist also."

Kristin Cavallari, New York Fashion Week, fashion, style, dress, headband
Cavallari wore her first pair of designer shoes to this New York Fashion Week in 2006.Getty Images

"This was New York Fashion Week. This was my first big fashion week, and I was here for a week and I went to a million shows. And I have never done that since. Now, I'll go to, like, maybe one or two shows, because it's a lot. But at the time, I really liked this outfit," she said. "I thought this was a really great moment. And, you know, I think it could be worse. I remember these were Marc Jacobs shoes and one of the first designer shoes that I bought. So, I was really feeling myself here. And, yeah, I kind of wish I lost the headband — the blue headband that doesn't match at all — and those earrings are a little crazy. But other than that, you know, not horrible, not my worst."

Kristin Cavallari, fashion, red carpet, style, yellow dress, Golden Globes
Kristin Cavallari admits she's "still mad" about this look.rer / Getty Images

"I'm still mad about this one. This was at Golden Globes InStyle party. And I just kind of wish that my stylist introduced me to Spanx at the time, because this is not cute. What's happening right here is not cute, and the hoops are a little aggressive."

Kristin Cavallari, red carpet, Golden Globes, naked dress, gold dress
This was Cavallari's first time trying the "naked dress" look. WireImage

"This was the Golden Globes, recently. And I actually used a new stylist here for the first time — Mimi Cuttrell," she said. "But this was a very daring look for me. I had never done the naked-dress look before, and so it was a risk.

"I liked it. It's not necessarily my personal favorite style. But this is why these award shows are so much fun because it's like playing dress up and you can just kind of go for it and wear something that you wouldn't normally in your everyday life."

Kristin Cavallari, red dress, red carpet, Amazon, old Hollywood
As a blonde, Cavallari often says no to red, but this classic look was a worthwhile exception!WireImage

"This is the Golden Globe InStyle after-party, the most recent one. And this is actually one of my favorite dresses that I've ever worn. I don't normally wear red and I actually told my stylist, 'I'll do anything but red.' And she brought this dress, and we were like, 'Oh well, all right, well, let's try it. We like it.' And I ended up loving it. And I did the old Hollywood glam hair, and I had the diamonds. This was a very classy moment, and I really love this.

"(My husband) Jay (Cutler) is very opinionated. And he is not afraid to tell me if he hates something. And then he'll also tell me when he really loves something. He actually loved this," she said.

When it comes to her personal style, Cavallari said she's proud of her journey.

"I think that my style has come a long way. I'd say I'm very effortless-chic, no matter what it is in my life, whether it be clothes or how I'm decorating my home. I'm just drawn to simplicity and I never want to look like I took too long to get ready," she said. "But before I realized what my style was, I played with a lot of different styles, and I had a lot of different people putting clothes on me. And so I was just kind of figuring it out. I didn't realize what I really was drawn to until I'd probably say, like, five years ago or so."

And when the time comes, she'll be happy to share her fashion finds with 3-year-old daughter Saylor James Cutler.

"I'm going to give my daughter my entire closet," Cavallari said. "I mean, she already will go through my closet and anything that's pink, she's like, 'Mine?' And I'm like, 'You can have that when you're older.'"