Look Back at Britney Spears' Cutest Mommy Moments and Best Family Photos

Enjoy these pics of the singer and her two boys

By Elyse Dupre Aug 05, 2019 7:19 PMTags
Britney SpearsInstagram

Britney Spears is one "Lucky" lady.

The 37-year-old singer took to Instagram on Sunday to share a few photos of herself enjoying a day at Disneyland with her sons Sean Preston Federline and Jayden James Federline. The Grammy winner noted the trio had a "great time" at the California park and even took a ride on Splash Mountain.

"My boys are older now, so they don't like their picture taken ever... so I was thrilled today when they said SURE !!!!!" she wrote in part of the caption. "Such a great place !!!!!"

It's hard to believe the boys are already in their early teenage years. As fans will recall, Spears welcomed Sean, now 13, with her now-ex Kevin Federline in 2005. The pair then welcomed Jayden, now 12, a year later. 

Over the years,  Spears has enjoyed several memorable moments with her boys. To look back at a few of their cutest family photos, check out the gallery.

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Enjoy the trip down memory lane!

Watching Them Grow

"It's so crazy how time flies .... My boys are so big now!!!!" Britney writes 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 captions 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 shares 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 captions the 2018 post.

Granting Your Wish

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


Spending Sundays With Mom

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

Traveling Abroad

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

Catching Some Waves

The boys and their mom do 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 writes in 2017.

Exploring Life Under the Sea

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

Getting Ready for the Holidays

Spears and her boys celebrate Thanksgiving with their famous 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 celebrates July 4, 2015 at the Happiest Place on Earth. 

Soaking Up the Sun

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

Looking So Grown-Up

Spears is one "Lucky" mom.

Walking the Red Carpet

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

Posing for the Camera

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

Perfecting the Pout

Look at these cuties!

Wearing Some Spooktacular Costumes

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

Celebrating Mother's Day

"I've got the two cutest boys in the world!" she captions the 2013 pic. "I hope y'all are having as nice of a #mothersday as I am!"

Enjoying a Movie Night

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

Having a Ball

The boys enjoy 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 takes her sons to the Broadway production of The Lion King in 2011.

We can't wait to see more adorable family photos in the future!

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