Jamie Lynn Spears' 17-year-old daughter, Maddie, is flying by those pivotal high school milestones - and her mom can barely cope. "But like how are we already trying on dresses for her SENIOR prom?" Spears, 34, wrote via Instagram on Friday, February 13. "Thanks to @sherrihill & @girligirl_boutique for always making these precious mother-daughter moments even more special." Maddie, Spears' daughter with ex Casey Aldridge, tried on a handful of prom dresses in her social media footage. "They sent me this huge box of dresses," the teen said in a video. "I'm gonna try them on for y'all, and you're going to have to help me pick which one is the best one." Jamie Lynn Spears 'Fought Hard' for Daughter Maddie's Prom Shoe Choice Maddie began her try-on haul with a mermaid lilac gown that she thought was "gorgeous." She continued, "And then the back, I love the back," before trying on a ballgown in the same lilac print. "It's a different style than the last one." Next, Maddie donned a slinky black dress that was dotted with pearls. Courtesy of Jamie Lynn Spears/ Instagram "This prom season, pearls are very in," she said. "This is perfect, and then the back is actually gorgeous. It has a little bit of a train." Maddie then tried on a similar black, pearl gown that featured a dramatic leg slit and a corset bodice. She continued looking at blue, gold, magenta and pink floral frocks. Spears, meanwhile, couldn't resist joining in on the fun and tried on Maddie's dress options. "Ivey, what do you think?" Spears asked her 7-year-old daughter Ivey, whom she shares with husband Jamie Watson, about a beaded floral dress. "Should I wear this to [school] pickup?" See Every Time Celebrity Kids Wore Their Parents' Red Carpet Outfits While Ivey didn't want her home to pick her up from school in a gown, she did suggest that the gown showed off too much cleavage. Spears eventually stepped out of the gown, leaving Maddie free to pick her favorite one. "I love dresses that are super sparkly and cute," Maddie quipped. "Thank you so much for watching. I also have this cute little Sherri Hill merch they sent me. ... Thank you so much Sherri Hill and Girli Girl Boutique, I had the best time trying on these dresses. I'm gonna need y'all's help to see which one I should wear for the senior prom." Maddie's try-on video comes weeks after her "miracle anniversary," which Spears marks annually to honor the teen's near-fatal ATV crash. Jamie Lynn Spears' Daughter Maddie Commits to College for Softball "I will never take for granted the gift we were given, bc I'm very aware that so many times in these situations that is not the case," Spears wrote via Instagram earlier this month on the ninth anniversary. "Thank you to every first responder, medical professional, friend, family, every single person who prayed for her, and ABOVE ALL THANK YOU GOD🙏🏻 go love on your people extra today, at the end of the day that is all that really matters." Maddie had been riding an ATV in February 2017 when the vehicle flipped over into a pond. Maddie was knocked unconscious and remained underwater for several moments before being airlifted to the hospital. "I did have an accident, though. I was in a coma and I came back to life, and I'm very blessed," Maddie recalled in an August 2025 social media video. "I've just been very accident-prone. I swear my parents are amazing, and they did not do anything to me."