Kristin Cavallari Through the Years: Photos (2024)

Kristin Cavallari made waves on Laguna Beach in the early 2000s, and she’s been entertaining Us ever since.Cavallari made her reality TV debut in 2004 on season 1 of Laguna Beach. She returned for season 2 and later stirred the pot on The Hills following Lauren Conrad’s departure.After finding love with former NFL quarterback Jay Cutler — the two tied the knot in 2013 — Cavallari stepped back from reality TV and focused on her own brand, Uncommon James, and several cookbooks. She also turned her attention to the pair’s three children: Camden, Jaxon, and Saylor.Cavallari and Cutler had their own reality show, Very Cavallari, which documented her business in Nashville. The E! series lasted three seasons before ending in 2020. That same year, Cavallari and Cutler announced their divorce.“There’s good days and bad days, but I’m feeling really good right now,” Cavallari exclusively told Us Weekly of her recent ups and downs in October 2020. “I’m feeling really happy and really free and that’s a nice feeling.”Scroll down to see Cavallari’s evolution over the years:

Cavallari was a full-time cast member on the first two seasons of Laguna Beach.

Cavallari has made headlines for a series of high-profile romances over the years, including relationships with Brody Jenner and Nick Zano and had a fling with Nick Lachey.

After wrapping up her original reality TV run, Cavallari tried to transition into acting, landing a role in Amy Poehler’s Spring Breakdown in 2008.

News broke in 2009 that Cavallari was replacing Conrad on The Hills. She made her first appearance at Heidi Montag and Spencer Pratt’s wedding during season 5 that same year. Cavallari starred on the MTV series until its July 2010 finale.

Cavallari and Cutler met in 2010 after Giuliana Rancic, who lived in Chicago at the time, introduced her to the then-Chicago Bears quarterback.

Cavallari and Cutler wed in 2013 after they welcomed their first son in 2012. She gave birth to their second son in 2014. One year later, daughter Saylor was born.

The reality TV personality became a full-time part of E!’s awards show coverage in 2017 after working for the network for years.

Cavallari and Cutler put on a united front during the three seasons of her E! series, which aired from 2018 to 2020.

Cutler and Cavallari announced their split in April 2020.

Months after her split from Cutler, Cavallari made headlines for cozying up to Colletti for a sweet snap in August 2020. She later confirmed they are just friends.

“I mean, I knew that like some people would be like, ‘Oh my gosh, so exciting!’ But I had no idea to what extent. I still think it’s pretty funny,” she told Us about the fan frenzy surrounding the pic. “I also think it’s really cool that people are still so invested in it and it really brought people back to that time in their lives. … It’s kind of hard to believe, so the fact that people are still so invested in Stephen and I and you know, our relationship, it’s sweet. It’s very sweet and I love Stephen. We had a good time and it’s all good.”

“I think at the end of the day, my kids are really the only thing that matters, and good friends too,” Cavallari told Us and other reporters in November 2020. “Just all of your people in your life are what really matter.”

In October 2020, Cavallari was spotted kissing Jeff Dye in Chicago. A source later told Us that their romance is "super hot and fiery" as they get to know each other and that he loves her "dominant personality." They were spotted kissing again in Nashville in November. While neither confirmed the relationship, they continued to leave flirty comments on each other's social media posts.

In January 2021, both Cavallari and Cutler posted a photo of the pair together with matching captions via Instagram: "The world is full of users. 10 years. Can’t break that." Despite fans hoping the post meant they were getting back together, an insider confirmed to Us that they're just friends and always will be for the kids.

Cavallari posted a Valentine via her Instagram Story in February 2021. “Dear J, You can skip the chocolate this year,” the note read. “I want tequila, a beach and [the] Secret Rose candle at Uncommon James. … Xoxo KC. PS. T minus 12 days. You’ve got this.” Dye then posted something similar, which read, "Dear K, You can skip the distance this year. I want drinks, dancing and you from Uncommon James. Xoxo, Jeffy."

Us confirmed in March 2021 that the former reality TV star and the comedian pulled the plug on their casual romance after five months. They “were never officially together,” an insider told Us at the time noting, “Kristin is doing her own thing and focusing on building her brand Uncommon James.”

Cavallari opened up her third brick-and-mortar for Uncommon James in Dallas in March 2021. “Dallas!!! You guys have always been the most supportive — thank you for welcoming us with open arms. I couldn’t be more excited to open our third doors here,” the businesswoman wrote via Instagram while celebrating the grand opening. “I’ve always said the Dallas girl embodies who we are as a company — she is fashionable, confident, strong, and FUN. Love you guys from the bottom of my heart.”

The TV personality sparked romance speculation in late 2020 when she became pals with Southern Charm’s Austen Kroll and Craig Conover. Cavallari, however, denied that she was anything more than friends with both men via social media in July 2021.

“I haven’t been involved in a love triangle since I was in high school,” she wrote at the time, referencing her Laguna Beach romance with Colletti, who was also flirty with Conrad as teens.

Cavallari said it’s “not true” that she is romantically involved with Kroll or Conover, adding that she is “not dating anybody” at the moment. “These two guys who I have been linked to for the past year are my friends. That’s it,” she explained. “I’ve never dated either one of them. I can guarantee that I’m not going to date either one of them. It’s possible for a grown woman to be friends with a grown man.”

Us confirmed in August 2021 that Cavallari was causally dating singer Chase Rice. “It’s still very new, but they really like each other,” a source said at the time. “They’ve been spotted around Nashville on a couple of dates, she’s been to one of his shows and they’re taking things slow.”

Two months later, the working mom revealed that she is single despite being spotted with the country musician around Nashville in the summer. A source told Us in October 2021 that the pair had “casually dated and had fun” but there was “no official label.” The insider added that Cavallari is “too busy with her business and her kids” to keep the romance going.

The Hills alum revealed in September 2021 that she was filming a new project but kept the details under wraps. “Kristin is filming a new show that’s not based on her life per se, but on something else,” an insider close to Cavallari told Us at the time. “Her best friend Justin will be in the new show as well. Details will be revealed at a later time.”

Cavallari reunited with Laguna Beach costar and high school sweetheart Colletti to cohost the “Back to the Beach” podcast. The duo launched the podcast in July 2022, discussing season 1 of the MTV series. In 2023, they returned to recap season 2 of the reality show.

Cavallari launched a new podcast titled “Let’s Be Honest With Kristin Cavallari” in September, exclusively telling Us she planned to tell it all. “This is the first thing I’ve done where I’m like, ‘This is the real me for the first time in my entire career. I’m in a really good place in my life, and I feel like I can finally open that door and let people in,’” she said of the new venture.

During the same interview, Cavallari teased that she was “dating” after going through “phases of going on a million first dates” and other periods of “not dating at all.”

She revealed: “I still very much believe in marriage and love. I was just really young when I met my ex. So, yeah. I’m open to it — even after all these horrible dates!”

In February, Cavallari opted for a hard launch for her relationship with model Mark Estes. At the time, she shared a photo via Instagram with the young man, who is 13 years her junior, from a tropical getaway to Mexico.

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