See Jamie Lynn Spears' Teen Daughter Maddie Watson All Dressed Up for Homecoming Court

Jamie Lynn Spears' 16-year-old daughter Maddie Watson—who she shares with ex Casey Aldridge—wore not one, but two Legally Blonde-inspired looks for her high school homecoming court.

By Gabrielle Chung Sep 19, 2024 1:39 AMTags
Watch: Jamie Lynn Spears' Daughter Maddie Looks All Grown Up in Prom Pics

Jamie Lynn Spears' daughter Maddie is thinking pink for homecoming.

In fact, the 16-year-old—who Jamie Lynn shares with ex Casey Aldridge—wore multiple looks in the rosy hue as she recently served on her high school's homecoming court.

As seen in photos shared by her mom Sept. 15, Maddie twinned with her 6-year-old sister Ivey—who Jamie Lynn shares with husband Jamie Watson—in a pink-and-black tweed blazer and matching skirt during daytime celebrations on the school football field. The teen completed the Legally Blonde-inspired look with a black facinator and heels.

For her homecoming dance, Britney Spears' niece turned to a pastel pink mini-dress featuring an embellished straps and empire waist details. Maddie kept the accessories simple this time around, opting for white Mary Jane heels, stud earrings and a few bracelets.

And pink seems like Maddie's go-to color for special occasions. After all, she wore a fuchsia-colored gown to her prom in April. 

The stunning attire featured sequins throughout as well as a high thigh slit, prompting Jamie Lynn to quip on Instagram at the time, "5 to 15 happens reallll quick."

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And when Maddie celebrated her Sweet Sixteen in June, the Zoey 101 alum marveled at how time flies as a mom.

Instagram

"16 years ago I fell in love for the first time, and loving that sweet baby girl saved my life in so many ways," Jamie Lynn—who was only 17 when she gave birth to Maddie—wrote in a birthday tribute to her daughter. "It wasn’t always easy, and surely farrrr from perfect, but I have always been so proud to be her mama."

The now-33-year-old continued, "She’s everything I prayed for, I thank God for every birthday we get to celebrate her, and won’t take a second of it for granted."

To see more of Jamie Lynn's family moments with her kids, keep reading...

Play Ball

In November 2024, Jamie Lynn Spears announced that Maddie Watson—who she shares with ex Casey Aldridge—has committed to playing college softball with the University of Southern Mississippi. She shared a photo of herself and Maddie visiting the campus with husband Jamie Watson, with whom she shares daughter Ivey Watson

Time Flies

"I can remember it like it was just yesterday, as the whole world watched and judged as I made the choice to have my baby at 16 years old," Jamie Lynn—who became pregnant with Maddie when she was a teenager—wrote in a November 2024 Instagram post. "Fast fwd to today, and that same little baby girl is now 16 years old herself announcing that she will be going to play D1 ball for an amazing college."

Home Is Where the Heart Is

Jamie Lynn perfectly coordinated with daughters Maddie and Ivey during homecoming in September 2024.

Bring Your Kids to Work Day

The actress was joined by her daughters on the set of Zoey 102 in 2023.

Mini Milestones

Jamie Lynn and Maddie celebrated Ivey's kindergarten graduation in May 2024.

Prom Night

Maddie looked all grown up posing next to her mom and her date before her junior prom in April 2024.

Under the Christmas Tree

The family was feeling festive on Christmas 2023.

Motherhood Moments

"I know motherhood is one of the hardest job at times, and how the mother/child relationships can be really complicated as well," Jamie Lynn captioned this throwback photo on Mother's Day 2023. "I really try to not take any of it for granted though, even when the kids or my mom are making me lose my mind."

Hoppy Family

Jamie Lynn celebrated Easter 2023 with her husband and two daughters.

Homecoming Surprise

The Sweet Magnolias actress said she drove seven hours to surprise Maddie at her homecoming in 2022, writing on Instagram, "Nothing else I’d rather do & Nowhere else I’d rather be."

Bath Time

Jamie Lynn proved that a mom's job is never done in this 2020 snap, which she captioned: "Been making hotels and buses all around the world feel like home since I can remember, and now I get to make those same kind of memories with my girls."

Girls' Night

In October 2016, Jamie Lynn brought Maddie to witness her receive an award from the Nashville Songwriters Association International for her work on the Jana Kramer smash hit "I Got the Boy."

Play Ball

The family celebrates Maddie and her softball team's 2019 SEAA World Series win in July 2019.

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