Revisiting Britney Spears' Sweetest Photos With Her Sons Over the Years

Sean Preston Federline and Jayden James Federline made a rare Instagram appearance on Oct. 5. Scroll on to see more photos of Britney Spears and her sons.

By Elyse Dupre Oct 07, 2021 3:25 PMTags
Watch: Britney Spears Shares Rare Update on "Extremely Independent" Sons

Kids, they grow up so fast.

Sean Preston Federline and Jayden James Federline were proof of that when they made a rare appearance on Instagram on Tuesday, Oct. 5.

The 16- and 15-year-old sons of Britney Spears and Kevin Federline were spotted in a few pictures posted by Eddie Morales, a friend of K-Fed's. The teens smiled as they stood next to the Movision Entertainment CEO in the photos, and Eddie showcased Jayden's musical talents by sharing a video of him playing the piano.

In addition to posting photos and a video of the brothers, Eddie shared a few snapshots from a hangout with Kevin and a few others.

"During times of grief knowing u have #family really feels worth living," he wrote in part of the post. "Talk bout seeing my nephews when they were pods smaller then my hands now look at #life how beautiful gods work…love you bro @federline4real." 


Britney Spears Through the Years

Despite living in the public eye, Britney and Kevin, who married in 2004 and finalized their divorce in 2007, have tried to protect their kids' privacy. In a September Instagram post, the 39-year-old singer, who is now engaged to Sam Asghari and whose father Jamie Spears was recently suspended as her conservator, called Sean and Jayden "extremely independent little men."


"There's a lot I can't share with you all because my kids are very private which I love but I will tell you they are both extremely talented and I'm so incredibly blessed to have these two little men in my life!!!," Britney wrote. "And if they're reading this … which I'm pretty sure they're not … I love you two little devils so much!!!"

To look back at their family photos from over the years, scroll on.

Watching Them Grow

"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."

Visiting Disney

"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!!!!!"

Doing a Little Painting

Spears shared a video of arts and crafts time with her sons in 2018.

Sharing a Laugh

"Getting silly with my kids on our day off from tour!" the artist captioed the 2018 post.

Granting Your Wish

"This was from our lil trip to see Aladdin," Spears captioned the 2018 photo. "What a great show!!!!"


Spending Sundays With Mom

"Love when we go to our favorite spot on Sundays," she wrote on Instagram in 2018. "The boys are bigger than me now!!!!!"

Traveling Abroad

The family enjoyed a trip to London during Spears' Piece of Me Tour. 

Catching Some Waves

The boys and their mom did a little surfing during their 2017 trip to Hawaii.

Playing With Their Pup

"Going for a walk with my son and the dog always does wonders for my mood..." she wrote in 2017.

Exploring Life Under the Sea

The dynamic duo saw some aquatic creatures in Las Vegas in 2016.

Getting Ready for the Holidays

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.

Riding the Rides

The "Oops...I Did It Again" star celebrated July 4, 2015 at the Happiest Place on Earth. 

Soaking Up the Sun

The "Toxic" singer shared a picture of her enjoying "the mermaid life" in 2015.

Looking So Grown-Up

Spears' boys are all grown up.

Walking the Red Carpet

The artist's sons helped her hold up her surfboard at the 2015 Teen Choice Awards.

Posing for the Camera

The terrific trio shared a sweet smile in this 2015 pic.

Perfecting the Pout

Look at these cuties!

Wearing Some Spooktacular Costumes

The singer and her two boys went all out for Halloween 2014.

Celebrating Mother's Day

"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!"

Enjoying a Movie Night

The proud mama took her boys to see the Los Angeles premiere of Smurfs 2 in 2013.

Having a Ball

The boys enjoyed a sweet treat with their mom at this 2013 game between the Los Angeles Dodgers and the San Diego Padres.

Taking in a Show

The singer took her sons to the Broadway production of The Lion King in 2011.