Inside the Reinvention of Kristin Cavallari: How She Transformed From Reality Bad Girl to Boss Mogul

By Sarah Grossbart Jan 09, 2020 2:30 PMTags
Watch: Kristin Cavallari's Best Boss Moves

When MTV viewers headed for The Hills last year, one familiar face wasn't amongst the cast.

While Kristin Cavallari allows that a cameo on MTV's reboot of their mid-aughts reality phenom would be a fun exercise in nostalgia, anything more would be a bit much. "It would have been tough to kind of go back to that whole lifestyle and all of that drama," she admitted to Us Weekly last year. "I talked to Audrina [Patridge], she said it's been hard for her. So, yeah, I'm kind of happy that I kind of don't have to go back to that."

These days, the closest the teenage reality star turned actress turned shoe designer, cookbook author, store owner and lifestyle mogul gets to the 22-year-old schemer that eagerly signed on to fill the series' bad girl role is watching the oft liquor-fueled histrionics that occur amongst the young staffers that make up her thriving Uncommon James brand and the cast of her E! series Very Cavallari. (Well, that and the time she overdid it on the tequila shots during a company trip to Florida.) 

Remarking on a dustup between two employees on a season 2 episode of her show, on which she serves as star and executive producer, she observed to stylist Kelly Henderson, "This is s--t I did when I was 22. You've got to grow the f--k up." 

Very Cavallari: Meet the Cast!

That's something the 33-year-old has definitively done in the decade since she walked off an MTV soundstage (the final scene itself a cheeky wink to the is-it-real-or-fake discussions that perpetually circled The Hills). It's not just that she's nearly seven years into a marriage with former NFL quarterback Jay Cutler or the mom to their three kids, sons Camden, 7, and Jaxon, 5, and daughter Saylor, 4. It's that she literally can't imagine reliving a single one of her youthful indiscretions. 

"I am too old for that s--t. I don't want to have those catty girl fights, that's just so not my life anymore," she told Paper magazine in 2018, dismissing the idea that she'd one day lead the cast on, say, The Real Housewives of Nashville. "I had to go back and watch clips from Laguna Beach and The Hills and it made me cringe because, ugh, that was my world! Fighting about the dumbest shit on the planet. Whether it was amplified or not, I was still doing it and I want no part of that anymore."


In other words, Toto, it's so not 2004 anymore. Denver-born, Chicago-raised Cavallari was just 17 when MTV execs showed up at her Laguna Beach, Calif. high school on the hunt for a group of charismatic teens who could front their new brainchild: a real-life, docu-soap version of Fox's runaway drama The O.C. When they found the outspoken blonde junior, her dreamy senior boyfriend Stephen Colletti and his best friend Lauren Conrad, the perpetual girl-next-door who'd been harboring a secret crush, one development exec sent back word to the network: They had it.

With Conrad as narrator, Cavallari was introduced to TV audiences—as she floated into view on a pool raft—from her rival's perspective. "That? That would be Kristin," sniped the future fashion designer of the bikini-clad high schooler. "Wherever Kristin went, drama followed."

At issue, continued Conrad, "She can't stand me. Here's the reason why: Stephen. I guess he's kind of her boyfriend, but Stephen and I have been really close forever….Kristin's the wrong girl for him."

The Hills & Laguna Beach: Where Are They Now?

And with that, the photogenic teen was slotted into the requisite villain role, a label that stuck with her as she went toe-to-toe with classmates and struggled to make her teenage romance work.

For producers, she was reality TV gold, the love-to-hate-her character that kept some three million-plus viewers tuning in each week. "What I loved about it was Kristin seemed confident, fearless and really unconcerned with school politics and everything going on around her," executive producer Tony DiSanto told The Washington Post last year. "She was paving her own way."

But for all of her boldness, Cavallari didn't actually relish playing the bad girl. She'd log into chat rooms and see people trashing her, and in a land before social media her only real recourse was to take it. "I didn't look at myself as a star. I looked at it more like, 'Everybody hates me,'" she told the paper. "That was really tough for me, being so young."

In one of the show's more infamous scenes, a newly single Cavallari dances atop a bar in Cabo San Lucas, Mexico as her ex Colletti disparages her from across the room, yelling out, "Slut!"

Charming, really. Yet somehow it was Cavallari who came off looking bad…


Looking back now, she's able to brush off the incident. "I wasn't even doing anything!" she told Cosmopolitan. "I got so much s--t for that—I mean, they made it seem like I was the only one up on the bar dancing that's what everybody does in Cabo. I still go to Cabo. People are still dancing in the bars. And I wasn't with Stephen. But no, I was the bad guy. Just living my life, man."

But the experience was undoubtedly difficult. "It definitely affected me," she admitted to Paper, "but because of that, at such an early age, I had to learn how to shrug it off and think, "It's just a show, these people don't actually know me."

So when MTV producers came calling again in 2009—after a stab at acting left Cavallari with just a handful of credits on Veronica MarsCSI: NY and Van Wilder: Freshman Year—she realized it was a proposal she shouldn't refuse.

Miranda Penn Turi/MTV

Former foe Conrad had just announced intentions to leave The Hills, maneuvering her black BMW convertible into a bright future as the designer of LC Lauren Conrad, Paper Crown and an all-around lifestyle doyenne. And Cavallari saw her chance to write out the rest of her story. The exposure (nearly 5 million tuned in to watch attractive twentysomethings party at Les Deux and fight over guys that likely weren't worth their time) could set up the next phase of her career and the paycheck certainly didn't hurt.

"The money was the reason I did it," she told Us Weekly in 2016. "Producers gave me an offer I couldn't refuse. I'm glad I went back to [reality TV] because this time I looked at it strictly as a job and I knew the character they wanted me to play." So if the network was going to trumpet her premiere with the tagline, "The b--ch is back," she was happy to go along.

"At the end of the day, if a b--ch means that I go after what I want, I speak my mind, and I'm not going to let people walk all over me, then call me a b--ch. Great. I'll take that," she explained to The Washington Post. "Because those are all things that I am."


This time around she had no trouble strolling into a party and chatting up pal Audrina Patridge's non-committal pseudo boyfriend Justin "Bobby" Brescia, for instance, or striking back when Stephanie Pratt accused her of playing dirty by trying to make a move.

"This is what happens after a bottle of tequila," she laughingly noted to Cosmopolitan of the scene that saw her taking on Pratt. "Is it going to be like this? Because if it's going to be like this, it's f--king on b--ch. It's on!" she screamed in the clip. "You're f--king with the wrong girl."

This girl was happy to indulge in a few catfights or flirt with former boyfriend Brody Jenner, if that's what was asked. Unlike Laguna Beach, which made storylines out of her real life high school romance, "With The Hills, those people weren't really in my life until I joined the show. I had known a lot of them, but they really weren't in my circle of friends. It was very separate, which made it easy in that sense," she noted to Paper. "When I did The Hills, I knew I had to keep things separate because it's very easy for the lines to get blurred and I didn't like that feeling."

John Sciulli/WireImage for Angeleno Magazine

Approaching it as an exercise in role playing, made her season-and-a-half return pretty enjoyable. "We knew exactly what scenes we were going to be filming and what it was going to be about," she told the mag. "I had fake fights and fake relationships. I was playing up the villain and was acting essentially. I had a really great experience."

Still, when filming ended in 2010, Cavallari's entire brand was wrapped up in her mean party girl persona, so she pivoted hard. Her turn on MTV had attracted the attention of veteran NFL quarterback Cutler—"My publicist called me when I was filming The Hills and said Jay wanted to fly me to Chicago to take me on a date," she would later share with People—but she'd returned the request down flat. "I didn't want a boyfriend, especially one who lives in Chicago."

But a year later, with her days on reality TV in the rearview, she went to a Bears game with her family and in an effort to impress her Illinois-based kin, she secured passes to meet the athlete afterward. "He walked in and he was so good-looking and so sweet," she recalled. "We hung out a couple nights later. Then things moved pretty quickly."


After two weeks, the former Vanderbilt star, 36, was professing his love. Not quite two months after that, he admitted he wanted to marry her. "We got engaged after eight months!" noted Cavallari of his 2011 proposal.

Moving at warp speed led to some growing pains, with the pair briefly calling off the engagement. "I needed Jay to know that I was serious about some things and I needed to go to extreme measures," she told People. "Deep down, I knew in my heart things were going to get better if I broke up with him."

Which they did thanks to a commitment to couple's therapy. "We've gotten to a place to have more empathy and more compassion for one another," she said during an appearance on SiriuxXM's Wake Up With Taylor. "Because you learn why, you know everyone comes with a certain amount of baggage. We all react to different situations differently."

When Cavallari took a spin through the Dancing With the Stars ballroom in late 2011, Cutler was in the audience, the duo confirming their betrothal was back on with little fanfare.

Kristin Cavallari & Jay Cutler's Cutest Pics

"It was so silly. I was in the airport, leaving Chicago," she shared with E! News. "We had just spent however many days together and we were texting and somehow it came up, like, 'Oh, shall we get married?' We're like, 'Yeah, OK.' And then he sent my ring in the mail. So I actually had my ring sitting at home for a couple of weeks before I put it on."

By August 2012, the pair, now settled in the Midwest, were welcoming their first son Camden. Their 120-person Nashville vows followed 10 months later ("Not to sound cheesy, but literally the entire day was perfect," she told CVLUX) and son Jaxon 11 months after that. The final piece of their family—daughter Saylor—would come along in November 2015.

"When I was becoming a mom, I really felt that I was doing the right thing for the first time in my life," she admits to Paper. "I had Camden when I was 25 so I was very young, but I had done so much by that time and had gotten everything out of my system. Becoming a mom was truly the next natural step for me. I would've never thought in a million years that I would be the first one to have babies and get married, but it's been the best thing that has ever happened to me, truly."

Heading up a family of five required a dramatic shift in priorities or, as Cavallari put it to Modeliste in 2016, "When you finally have kids, you realize how selfish you are." With Cutler traveling some six months out of the year, Cavallari needed to carve out a career that was flexible enough to make raising her children the priority.

"I have a shoe line and a jewelry line, and I can work on those from anywhere," she told BELLA New York mag of her collaboration with Chinese Laundry and Emerald Duv, a jewelry brand she launched with friend Chelsea Bulte. Same with the lifestyle tome, Balancing in Heels, she put out in 2016. "You know, I could write it in my spare time, when the kids are sleeping or my husband could watch them and let me write for a little while, and so I'm very fortunate to sort of have everything."

Kristin Cavallari & Jay Cutler Banter Over a Romantic Dinner

In 2017, everything expanded to include Uncommon James, with Cavallari craving the autonomy that came with owning her own company. What started as a desire to create delicate, sophisticated jewelry pieces at an accessible price point, expanded into home goods (a fitting swerve for a woman who put out True Roots, her New York Times best-selling cookbook based off her own healthy recipes) and, most recently Little James, for which her kids serve as both inspiration and fit models.

With Cutler's retirement from football following 12 seasons coming later that same year, Cavallari was able to slip back into a starring role. But this time she was determined to put forward her authentic self and the only "b--ch" label she'd be adopting was that of HBIC as the woman managing a now 70-plus employee lifestyle brand complete with a Nashville brick-and-mortar store, a new spot in Chicago, a robust online presence and a reality show—that returns tonight for season three.

"For the past seven years I've sort of been on his schedule, and with our kids, we just always want to make sure that one of us is around. And so with him being done, it just frees up a little bit more of my time," she told The Daily Beast, explaining why she felt the timing was right to launch Very Cavallari


"And then with us being in one location now, which is Nashville, I was really excited to plant not just my personal roots, but to open up my flagship store, my headquarters of Uncommon James, and with the staff that I have and the backdrop of opening up this store, I just felt like it was a really good opportunity to get back into reality TV—but not have it just be about my family, have it be about something more, and rely on the staff for the drama, rather than my own personal drama."

While her employees bring the antics and Cutler provides comic relief ("People think that he is the breakout star, which is fine, I'll let him have it," she says of her spotlight-stealing spouse), Cavallari is content to steer clear of the tears, only stepping in to remind staffers that she's there to run a company, not referee their personal dramas.

"I think now for me it's different because of a few things," she told Paper. "I'm not in the middle of the girl drama anymore; that's not my life anymore and it's great."


Her world is balancing her job as CEO and lifestyle guru with her marriage ("We've completely shifted roles," she told E! News of her and Cutler's relationship. And so it's just navigating this new normal for us,") and giving her kids as normal an existence as possible on their 10-acre Tennessee farm. 

Should she so desire to revisit her youth, it's there for the viewing. She knows one days her children will catch wind of her teenage years—"I'll just have to have a real conversation with them about the experience and everything that went into it, and I'm cool with that," she told Us Weekly. "I like having a very open, honest relationship with my kids,"—but until then she's happy to limit the nostalgia to particular moments, like when Cosmopolitan asked her to provide commentary on some of her greatest hits.

Her overall take: "I'm so happy that this isn't my life anymore," she admitted. "Just watching these clips, it's just like, 'Oh, I'm so happy I'm not in my early twenties and, like, this is my world.' Like, this was my world. I'm so happy that's in my past."

(Originally published March 24, 2019, at 3 a.m. PT)