Britney Spears Reunites With Sons Jayden, Sean Preston for Yacht Outing in New Video
Oops!... Jayden James Federline did it again—10 years later.
The 19-year-old son of Britney Spears and ex Kevin Federline walked his first red carpet since 2015, stepping out at the star-studded Dior Cruise 2027 fashion show in Los Angeles May 14.
For the occasion, Jayden rocked a forest-colored bomber jacket atop of a matching green plaid shirt and white tee. Keeping it casual, he paired his tops with baggy, distressed denim jeans and black boots.
But Jayden wasn't alone at the fashionable affair, posing for photos with a mystery brunette woman clad in a gray halter top, black trousers and pointed toe shoes.
Indeed, the teen has been making his way around the scene since moving back to L.A. from Hawaii, where his dad and stepmom Victoria Prince relocated to with the rest of their family in 2023.
"Jayden has already returned to L.A., chasing his music dreams,” Kevin wrote in his 2025 memoir You Thought You Knew, adding that his and Britney's 20-year-old son Sean Preston Federline is "finding his way as an adult."
"Watching both of them grow into themselves has filled me with pride," the backup dancer continued. "We’ve done everything we could to prepare them for life, and I know they’re ready."
In fact, Kevin, 48, described Jayden as a "firecracker" who's "brimming with creative energy."
Stefanie Keenan/Getty Images for Christian Dior; Monica Schipper/WireImage
"As a kid, he’d roar like a dinosaur or mimic sound effects with uncanny precision," he shared, "and now that charisma fuels his passion for music.”
And since his move back to California, Jayden has also been hanging out with his mom a lot more. He and Britney, 44, spent Christmas together, before the "Toxic" singer shared a photo of Jayden and his older brother on a boating trip this March.
"I better stay present whenever I can," Britney captioned the Instagram post. "I should disappear for how slow they went on that boat."
To see more of Britney's family photos with her sons, read on...
"It's so crazy how time flies .... My boys are so big now!!!!" Britney wrote in a March 2021 Instagram post. "I know … I know … it's very hard for any mama especially a mama with boys seeing them grow up so fast !!!! Talk about enough to make you go to your knees ... GEEZ !!!! I'm extremely lucky because my two babies are such gentleman and so kind that I must have done something right !!!! I haven't posted pictures of them for some time cause they're at the age where they want to express their own identities and I totally get it."
"Great time at Disneyland today .... but I don't remember ever getting that wet on splash mountain!!!" the "Stronger" star captioned an August 2019 Instagram photo series. "Geeez .... anyhow my boys are older now, so they don't like their picture taken ever... so I was thrilled today when they said SURE!!!!! Such a great place!!!!!"
Spears shared a video of arts and crafts time with her sons in 2018.
"Getting silly with my kids on our day off from tour!" the artist captioed the 2018 post.
"This was from our lil trip to see Aladdin," Spears captioned the 2018 photo. "What a great show!!!!"
"Love when we go to our favorite spot on Sundays," she wrote on Instagram in 2018. "The boys are bigger than me now!!!!!"
The family enjoyed a trip to London during Spears' Piece of Me Tour.
The boys and their mom did a little surfing during their 2017 trip to Hawaii.
"Going for a walk with my son and the dog always does wonders for my mood..." she wrote in 2017.
The dynamic duo saw some aquatic creatures in Las Vegas in 2016.
Spears and her boys celebrated Thanksgiving with their family members, including her sister Jamie Lynn Spears.
"Happy gobble gobble!" the Grammy winner writes in 2015.
The "Oops...I Did It Again" star celebrated July 4, 2015 at the Happiest Place on Earth.
The "Toxic" singer shared a picture of her enjoying "the mermaid life" in 2015.
Spears' boys are all grown up.
Steve Granitz/WireImage
The artist's sons helped her hold up her surfboard at the 2015 Teen Choice Awards.
The terrific trio shared a sweet smile in this 2015 pic.
Look at these cuties!
The singer and her two boys went all out for Halloween 2014.
"I've got the two cutest boys in the world!" she captioned the 2013 pic. "I hope y'all are having as nice of a #mothersday as I am!"
Jason Merritt/Getty Images
The proud mama took her boys to see the Los Angeles premiere of Smurfs 2 in 2013.
Jon SooHoo/LA Dodgers via Getty Images
The boys enjoyed a sweet treat with their mom at this 2013 game between the Los Angeles Dodgers and the San Diego Padres.
Angela Weiss/Getty Images for Disney's THE LION KING At Mandalay Bay
The singer took her sons to the Broadway production of The Lion King in 2011.
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