So what made Spears such a fashion icon?
It was Spears who helped usher in the crop top craze.
She was also responsible for helping make low-rise bootcut jeans look like the pinnacle of high fashion.
This hot pink leather crop top and cargo pants combo
Shiny, hot pink tube-style crop top?
Low-rise white cargo pants with knee pads?
High pigtails and shimmery makeup?
Thankfully, Grande gave us an excellent blueprint for how to update this look for many years to come.
Grande has totally inspired us to try this bold Y2K look for ourselves!
The pop star wore a long orange and purple lingerie-style jacket over a matching short set.
She also wore purple fishnets and, of course, a large choker.
However, there was a time when Spears wasn’t such a big fan of the look.
“I actually thought I looked hot at the time.
But, um, I definitely stood out,” she said.
I was a cheerleader for a school I didn’t know.
People were talking about it, but not in a good way."
Love it or hate it, this look is iconic.
She began the performance by wearing a black suit and matching fedora.
Designers Kurt and Bart designed the infamous outfit along with David Dalrymple.
Dalrymple shared ondaviddalrymple.comthat he believed the outfit was a “pivotal career moment” for him and Spears.
In 2018,Asosproclaimed that snakeskin pants were officially back in fashion thanks to designers like Isabel Marant.
Once again, it seems that Spears continues to be a huge trendsetter.
“It was elegant, classy, and the perfect gown for entering a new millennium.”
Spears continues to make an impact with this all-white outfit.
This Grammys outfit is undoubtedly one of the most iconic looks Spears ever gave us.
She coupled her loosely tousled hair with a live snake as if this bold outfit wasn’t enough.
If that’s not iconic, what is?
Clearly, the dress has served as inspiration for other stars over the years.
“I actually met Britney in person for this one.
It was lacy, sheer, had big slitted sleeves and was originally white.”
Campbell explained that designers Kurt and Bart suggested it should be green.
At the time, Spears was still relatively new to the pop music scene.
In fact, she ended up winning the award for “Favorite pop/rock new artist” that year.
She would only go on to wow her fans more as the years went by.
One of the most iconic pieces?
Her “Crossroads” bucket hat.
AsVogue U.K.noted, it was the perfect finishing touch for her character’s sweet all-American vibe.
This striking look is still remembered today.
This was one time when Spears opted for some old school glamour instead of her usual Y2K look.
As the singer toldHarper’s Bazaar, it ended up being one of her favorite looks of all time.
When asked by the magazine what her best look was, she described this look.
“It wasn’t short and saucy; it was a long red dress,” she said.
“That dress wasfun.”
In 2021, the star posted a photo of herself in the dress onInstagram.
“It’s taken me 19 years to realize that I was Julia Roberts in Pretty Woman.'”
