10 Ways to Wear the Billboard Music Awards Hottest Styles IRL

Juliette Lewis + Brad Pitt

We tend to think of Angelina and Jennifer as Brad’s two big loves, but before them (and Gwyneth) came Juliette Lewis. The two dated for four years when they were both on the cusp of total stardom. These two just might be tied with Johnny Depp and Kate Moss as the most ’90s couple that’s ever existed.

Michael Jackson + Brooke Shields

A budding supermodel and a global pop sensation? It’s kind of a Hollywood match made in heaven, just like Brooke's curls. That dress on the other hand? We’re not so sure.

Matthew Broderick + Jennifer Grey

As much as we’d like to believe Sarah Jessica Parker was Matthew Broderick’s one and only, this couple makes a lot of sense. The two were both the main characters in epic teen ’80s movies – we’ll just forget about the fact that they played brother and sister in one of them…

Jake Gylenhaal + Reese Witherspoon

Dang, why didn’t this couple work out again? Oh right, probably because that much wonderfulness packed into one couple would make the world explode. But they sure did look good together!

Drew Barrymore + Corey Feldman

Feldman once said that his first date with Drew was arranged by her mother when she was 10 and he was 14, because apparently Barrymore had a huge crush on him. They later dated briefly (this time for real) in 1989, when Drew was a teenager. Unfortunately, he was heavily into drugs during that time and she was trying to stay sober after multiple stints in rehab, so it didn’t last long.

Winona Ryder + Christian Slater

Here’s to hoping this relationship ended a little more amicably than it did for their Heathers characters.

Julia Roberts + Kiefer Sutherland

It was supposed to be one of the biggest Hollywood weddings ever, and then all of a sudden, Julia called it off. Tragic. At least we have this red carpet moment to remember the couple by.

Stacy Keibler + George Clooney

Now that Amal is in the picture, it’s hard to imagine George with anyone else. But before that British vision of elegance came Stacy Keibler, the stunning professional wrestler and George’s beau for two years.

Who’s your favorite throwback red carpet couple? Share with us on Twitter @BritandCo.

Did You Know This Fun Fact About the SJP & Matthew Broderick?

Sarah Jessica Parker and Matthew Broderick have known each other since 1991 — that's over 30 years! They've known each other and been married since 1997. SJP and Matthew Broderick also share three kids together whose names are James, Tabitha, and Marion. We just love their love and can't wait to tell you all about it below so keep reading!

A Full Relationship Timeline of Sarah Jessica Parker And Matthew Broderick's Love Story

November 1991/January 1993 — Sarah Jessica Parker and Matthew Broderick Meet

The two actually met through Parker's brothers who ran a local theatre in New York City. SJP was visiting the theatre to see her brothers' play and Broderick had recently directed a play at the very same theatre. The two met and a couple months later, Broderick sweetly left her a voicemail which led to the romance! We love a direct man!

After almost two years of dating, the new couple attend their first Golden Globes red carpet together on January, 23 1993 in Beverly Hills.

March 1996 — Sarah Jessica Parker and Matthew Broderick Work Together For the First Time

The two take their chemistry to the stage! After dating for five years, they decided to work together on Broadway for a play, How to Succeed in Business Without Really Trying. This was their debut of working together and it was so sweet!

May 1997 — Sarah Jessica Parker and Matthew Broderick Tie the Knot

The two finally get married after years of dating! They ended up doing a surprise ceremony for all of their closest friends and family to enjoy while SJP's sister officiated the ceremony. Sarah Jessica Parker didn't even wear white on her wedding day — what would Carrie think?

She later told Marie Claire in an interview, "I wore black on my wedding day, and I really regret that," Sarah Jessica Parker says. "I was too embarrassed to get married in white, and both Matthew and I were reluctant to have people pay so much attention to us. Which is ridiculous, because that's when you can relish the attention, when it's natural. We treated it like it was a big party on a Monday night, and I regret it."

But it definitely wasn't bad luck to not wear white because the couple is now revered for having one of the longest lasting marriages in Hollywood!

August 2002 — Sarah Jessica Parker and Matthew Broderick Are Expecting Their First Child

Sarah Jessica Parker was pregnant with her first son during filming for the fifth season of Sex and The City (although the wardrobe department did a great job at concealing the pregnancy for Parker's on-screen character). The couple remained very private throughout their whole pregnancy and birth.

September 2004 — Sarah Jessica Parker Wins Her First Emmy Awards

Sarah Jessica Parker won an Emmy Award for her role in our favorite show, Sex and the City. She thanked her three cast members in her speech and then went on to thank her family, including Matthew, who was of course sitting in the audience proudly watching her experience this incredible moment.

November 2006 — Sarah Jessica Parker And Matthew Broderick Are All Family

As it turns out, talent runs in the family as Matthew's mother, Patricia Broderick, was a well-known artist and playwright. Here they are pictured at an art show in New York that was honoring the late artist who had passed away a few years before this. Keeping family close is clearly important to the couple, as they remain a tight-knit family unit even now.

June 2009 — Sarah Jessica Parker and Matthew Broderick Have Twins

In 2009, the couple welcomed twins! Holy moly! The former group of three became five with the birth of their sweet twin babies. The twins are now in high school, believe it or not! Broderick said of the twins being super close on Live with Kelly and Mark, "When it was time to decide for real," Matthew explained, "they were like, 'No, we're going to the same high school.'"

March 2010 — Sarah Jessica Parker and Matthew Broderick Attend The Oscars

The pair showed up to stun at the 82nd Oscars together. They looked fabulous, in no surprise to anyone. In this photo, the pair had been together for around 17 years.

September 2011 — Sarah Jessica Parker Talks Parenthood

Fast forward to 2011 where their oldest is a toddler and the twins are still very young. We can't imagine the busy-ness for SJP and Broderick, balancing life and work while having three young kids under the age of five! SJP told E! that "Everyone should be scared of motherhood." She goes on to elaborate that, "It's good to be scared. You should be! Love is scary and friendship is scary and children, even more so." Well that we can definitely agree with!

June 2016 — Sarah Jessica Parker And Matthew Broderick On "Conscious Coupling"

The couple ditched their shared home and instead opted for two adjoining yet separate townhouses to create a better space for "conscious coupling" which allows them to work harder on their marriage and commitment to each other. They made the move as an effort to allow some individuality but still be a united front when it comes to their commitment to their marriage and staying together.

February 2020 — Sarah Jessica Parker and Matthew Broderick Star on Broadway Together

The showbiz stars paired up once more to do a show on Broadway in 2020! They reunited on stage together in Neil Simon's Plaza Suite play. SJP said of the experience in an article to the Hollywood Reporter, "I think we were more so thinking about the play, like, “How are we going to do this?” And I only thought about being concerned when people ask us, “Are you concerned that this is going to be harmful to your marriage?” And then I was worried. “Well, should we be?” We’ve never spent this much time together ever, even before we had kids." She later went on to say that despite it being strange to navigate that it was still a great experience to spend time together working!

December 2021 — Sarah Jessica Parker Premiers And Just Like That

And Just Like That, the show is back! SJP showed up in a stunning outfit with her sweet son and husband to support the return of her iconic show. She walked the carpet to celebrate her work with the two men in her life. It was a family affair!

Current Day — Still As In Love As Ever

While on Howard Stern's show recently, Sarah Jessica mentioned that her and Matthew Broderick haven't been apart since they met over 30 years ago. She said they have, "never spent a night apart since then, with the exception of work on location, or his mother was ill for a bit so he went to take care of her, but from that first night, we’ve never been apart.”

What else does she have to say about him after all these years? "It seems so silly, but I think you're very lucky if you like the person," she told People. "I still just really like him. I'm sure I annoy him and he annoys me, but I literally learn about him every day. I'm like, 'You're doing what? You're reading what?'

"I think marriage has a lot of vitality," she added. "If you're fortunate, it's like this dazzling organism."

We couldn't have said it better ourselves, SJP! This is a marriage that we are definitely still rooting for after all these years!

How did Kristin Cavallari meet her ex-boyfriend Mark Estes?

We're truly living in a digital age because TikTok is the reason Kristin Cavallari was introduced to her ex-boyfriend Mark Estes. She told her best friend Justin Anderson that she was scrolling down her timeline when she came across what she called a "boy group" called The Montana Boyz and they both agreed one of them specifically is her type. She said, "He's gorgeous. Like, everything about him is perfect. But, he's also outdoorsy and manly."

Three weeks later, she got a DM from The Montana Boyz that said "I love you" and she immediately let them know she wanted to have them on her podcast. Although the podcast didn't happen, Kristin Cavallari appeared in one of their TikTok videos. Once Kristin Cavallari learned from her assistant that they were planning to move to Nashville, she arranged for a line dancing meet-up with The Montana Boyz and her staff. After they met, Kristin decided to call the guy who would become her ex-boyfriend "Montana." (Cavallari used Montana as a stand in for her boyfriend's real name during the podcast recording as she never names anyone explicitly on her show.)

Shortly after that, Kristin Cavallari hard launched her new relationship with ex-boyfriend Mark Estes on Instagram in February, and the rest is history!

How did she feel about their age gap?

Kristin Cavallari didn't know how young The Montana Boyz were, but she wasn't interested in pursuing a relationship with Mark Estes at first. She did admit she had a brief issue with their age gap, but decided that Mark being 24 while she's 37 didn’t really bother her. Justin pointed out that she actually used to say she wouldn't date guys who were only 30 because she thought they were too young. However, she was more interested in who Mark was as a person and notes that life experiences and how you were raised is more indicative of one's maturity level than age alone.

Did Kristin Cavallari's kids like Mark Estes?

Kristin Cavallari said her boys were so excited to meet Mark for the first time and she felt like they really wanted her to be happy. "I've been really good about separating my dating life from their [life]," she said. Her oldest son especially approved of Mark and it was shocking to Kristin because he's usually the toughest judge of whoever she's dating.

How did her career prepare her for public opinions about their relationship?

Kristin Cavallari didn’t care what anyone thought about her ex-boyfriend. She's lived life in the public eye and is comfortable enough with herself to make decisions that make her happy. Kristin said, "...when this news came out, it's the first time in my entire life I 100% haven't given a sh-t what anyone thinks... My own mother is noticing a difference in me."

Did she mention anything about her divorce from Jay Cutler?

Kristin Cavallari and Jay Cutler were married for seven years before announcing their divorce in 2020. She didn't go into detail about it during the podcast episode, but she did talk about the magnitude of her former relationship with her ex-boyfriend. "It's the first time I've gone public since my divorce," she said.

How did Mark Estes adjust to being in the public eye with Kristin Cavallari?

Mark Estes may be in the spotlight because he dated Kristin Cavallari, but that didn’t mean he was enthusiastic about it. E! News caught up with him at the CMT Awards and he said, "It comes with the territory, I guess...It is what it is." One thing his friend Kade Wilcox — another one of The Montana Boyz — mentioned is that Mark was quite the romanticist when it came to Kristin Cavallari. He told the outlet, "He's pretty good at date nights."

How did Kristin Cavallari feel about dating a younger man?

Kristin Cavallari and Mark Estes may have been in bliss for a short while, but the former knows having an age gap in a relationship isn't always applauded by others. " I understand what it looks like from the outside world of, like, yeah, I’m dating a 24-year-old, but no one in my life has been like, ‘This is weird.’ Everyone’s like, ’I get it. It makes sense,'" she said (via Bustle).

She also said, "...Emotionally, he’s able to step up to the plate, and he’s shown up for me more than anyone else I’ve ever dated," (via Bustle). And according to her, Mark's all in when it comes to her kids and they love him for it. "He loves my kids. He actually took my kids to school, and it's just—he fits in very well. And I'm really thankful for that," (via E! News).

It's not easy balancing being an attentive mom who has a full-fledged career and relationship, but Kristin seemed grateful for the way Mark stepped up to the plate. She said he made things feel "so easy" which is something all moms crave!

Watch The Full Campaign Video For Hard Feelings Eau De Parfum 

Since talking about everything from her time on Laguna Beach to her relationship, Kristin Cavallari and Mark Estes appeared together in an ad campaign for her brand's new fragrance, Hard Feelings. It's described as an "alluring" scent that's meant to invigorate one's senses. With notes like pink pepper, hibiscus, and sandalwood, we don't doubt it's sensuality!

What's the steamy thing  Kristin revealed about her former relationship?

During the "Truth or Drink with Mark Estes" episode on Let's Be Honest with Kristin Cavallari, Kristin and Mark delved into steamy secrets about their relationship. The latter even dropped a bombshell when he admitted he enjoyed being intimate with Kristin. He said, "Yeah, you’re the best sex I've ever had for sure," which shocked her.

Though she liked his confession, she said she "didn't know that" before letting him know she felt the same. But, she attributed their hot sex to things like being "more present physically during sex" and being "wildly attracted" to Mark.

But, their relationship isn't all about their amazing romps in bed. Mark was “obviously so in love" with Kristin so that added to the spiciness factor!

Why did Kristin Cavallari And Mark Estes break up?

Sadly, all of the passion Kristin Cavallari and Mark Estes had fizzled out because they broke up after 7 months of being in a relationship (via Us Weekly). She told Alex Cooper, host of the Call Her Daddy podcast, the breakup was “fresh,” (via PEOPLE ).

It doesn’t seem like their breakup ended on a sour note, but we’ll see if they share more about it in the coming weeks!