Britney Spears Has Had Quite The Style Transformation

Britney Spears has been THAT GIRL, even before social media and that's something we do not say lightly. Though she had been a child performer on the "All-New Mickey Mouse Club" in the early 90s, she would truly go on to make a name for herself when she debuted as a breakout artist. From her beautiful voice, slick dance moves and natural beauty, Spears became an icon who every girl wanted to be.

With a career that spans decades, Spears practically grew up in front of the camera and we had the chance to see her change along with us. She went from the girl next door to finding herself as an adult artist, facing numerous personal struggles while under public scrutiny. Then like a phoenix, she appeared to rise above the ashes as a mother whose sons had no idea how important she been to pop culture. 

At 43, Spears may not fully be the star that Millennials grew up feeling as if we knew, but the fact that she is still here able to tell her story her way is all we could ask for. In addition to Spears totally transforming her hair through the years, her fashion has also evolved with every era. We still can't help reminiscing. 

Nothing is more iconic than Britney Spears' cover for her 1999 debut album "Baby One More Time." The first thing that we cannot help but notice is that the blond hair she had become synonymous with in the 2000s is nowhere to found. The blond bombshell is actually a brunette and is completely stunning with her natural hair color. Her red blouse, white tank top, dark-wash jean skirt and clunky wedges make her look like a Texas belle who reminded us of someone we may have known or seen. Unsurprisingly, Spears' favorite books are southern classics.

Plus, her outfit was so Y2K that reminds Millennials of a simpler time when we were jamming out to "Oops I Did It Again" on our Walkman's.

Britney Spears definitely gave "girl next door" vibes in those early days and again we cannot get enough of her natural brunette hair. While on the red carpet for the 1999 American Music Awards, her hair was in defined waves with straight bangs accessorized with a gold hairband. Though its not visible in this version of the photo, the singer rocked an ankle-length dress that featured spaghetti straps and a sheer asymmetric cut at the bottom. Her black strappy heels were such a cute touch, not to mention, an iconic look of its time.

During this red carpet appearance, Spears decided to keep her makeup light and airy, which allowed for her lips gloss and mascara to highlight her lips and eyes.

By the early 2000s, Britney Spears' star had reached the stratosphere and it was around this time that she was trying to break away from her previous "girl next door" image; she wanted to be taken seriously as an adult artist and her style began to reflect a more "sexy" image. During an appearance at the 2002 Teen Choice awards with little sister Jamie Lynn Spears, Britney wore an orange V-neck top that showed off a little cleavage with flowy sleeves, and an asymmetric cut that exposed much of her abs.

Of course, Britney was the queen of low rise jeans, which was such a moment. Another trend at the time was belly button rings and the one Britney wore in this photo was stunning. Also, here is that blonde hair that she and Jamie Lynn would become known for. (Fun fact: Jamie Lynn is also a natural brunette.)

By the late 2000s, Britney Spears was a fixture in the Hollywood social scene with paparazzi regularly photographing her outings with besties Paris Hilton and Lindsay Lohan. In this 2008 photo, Spears appeared to be glowing in her glam makeup and equally regal champagne sequined dress. This was several months after her very public breakdown in 2007 where she was filmed shaving off her famous blonde hair after losing custody of her two sons. In her memoir, "The Woman In Me," she wrote of that time that during that time without her children, "I lost it, over and over again."

Though this photo shows a smiling Spears, and we would get her highly anticipated "Circus" album, 2008 would also be a hard year as she suffered another public mental health crisis. This was also the year that her father Jamie Spears would be granted control over his daughter's estate, including financial, professional and personal decisions. This later controversial conservatorship would go on to last over 10 years and would be later reevaluated by fans.

In the 2010s, Britney Spears was in her mom era, taking her two sons Sean Preston Federline and Jayden James Federline to exclusive events. In 2013, the trio was photographed walking the blue carpet at the premiere of "Smurfs 2." Spears was rocking a turquoise bandage dress (which was all the rage during that time!) that had a wide black belt-like feature just above the waist. There is also black straps that reach the neckline from below the armpit. She also wore a minimal makeup look with a light pink lipstick and it is everything!

The love she had for her kids truly shined through the hundreds of photos taken of the trio at this time and this picture is no exception. From the outside looking it, it appeared that Spears was positively thriving as she would go on to be a judge for "The X Factor," in 2012 for 28 episodes. Then in addition to taking her kids to movie premieres, in 2013, Spears began her Las Vegas residency that was so popular, it would last for two years.

For several years, Britney Spears would step away from the limelight and it was during that time that fans began to reevaluate not only her conservatorship, but also the way media contributed to those public mental health crisis. With the end of her conservatorship in 2021, Spears became more active on social media, particularly on Instagram. It is on this platform where she posts videos of herself dancing, usually in a very scantily-clad outfit while rocking heavy eyeliner.

In this photo she posted in December 2024 wearing a red, off the shoulder mini dress with matching red lipstick with the caption, "perfect Instagram holiday!!!" Though Spears has worn very sexy outfits during performances and events, some that were considered inappropriate outfits during its time, her style appears to be in stark contrast to the star we all thought we knew growing up.

The #FreeBritney movement gained a lot of steam in the late 2010s and the early 2020s, which gave the pop star a voice. No matter where you stand on what she posts, we can all agree that it is a beautiful thing that she is allowed to express herself in her own way. It is also a testimony of how far we as a society has come from those days of scrutinizing young women so harshly, but there is still more work to be done.