In an Instagram post on Monday, the 38-year-old pop star shared a selfie, which featured Spears wearing a blue and white top, two choker necklaces and her hair pulled back.
"I know I need bangs 😜😜 !!!!! Who would have thought bangs could make you look waaaaay younger ?!?!" Spears began the caption of her post.
She continued: "I stopped having bangs in the 3rd grade and I remember like it was yesterday .... it was such a big deal to expose my forehead …. only pretty people in the south could do that and I never felt pretty enough to pull it off."
The "Toxic" singer went on to explain that beauty pageant girls did it, but Spears "never felt" like beauty pageants were for her.
"I had bad teeth and felt like an ugly duckling," she admitted. "I met with a modeling agency but I wasn’t pretty enough so I went home and said, 'maybe I can be like the older girls and show my forehead' !!!! I did and it looked sooooo bad but I thought I was gorgeous 🤣 !!!!
"I think I knew it didn’t look good but I did it because I thought it made me cool .... and I’ve pretty much had it like that ever since !!!!" Spears added.
The mom of two noted that people choose to protect themselves in "different ways," and for her, when she has bangs, she feels like she's "protected."
"Almost like I’m in 3rd grade again ⭐️💖🌸 !!!" she concluded her post.
On Saturday, Spears celebrated the 20th anniversary of her famed "Oops!... I Did It Again" album release. She took to social media to relish in the milestone by sharing a video.
The clip spliced together footage of Spears' music video for "Oops," as well as clips of her speaking about the record. She explained it was more "adult" than her previous music, even saying the album's first single was better than "...Baby One More Time."
Also included in the video: short shots of Spears dancing and enjoying herself.
"Thank you to whoever made this ….. I just nearly dropped my phone I wasn’t expecting it 😂😂😂 !!!!! 20 years since the Oops! 😳 album …. the anticipation and the butterflies 🦋🦋🦋 I felt before it came out were crazy …. all of my expectations were exceeded !!!!" Spears captioned the post.
She added: "And it’s all thanks to you folks …. thank you for sticking with me and growing with me. I am one Lucky girl ⭐️😉. God Bless and thank you all 🌹🌹🌹🌹🌹🌹🌹 !!!!!! PS you see even 20 years ago I still liked to twirl 🌀🌸🌸✨ !!!!"
Fox News' Nate Day contributed to this report