Britney Spears' Most Fierce Red Carpets Looks From 1998 To Today

Britney Spears, whose transformation is nothing short of stunning, wears many hats: singer, occasional actor, mother, queen of our Y2K hearts, and style icon. Since her debut single "...Baby One More Time" solidified her first hit in 1998, the Louisiana-raised pop star has graced a fair share of red carpets in her day over the duration of her seasoned career.

Some may identify Britney Spears as a pinnacle of 2000s fashion, but since 1998, the "Gimme More" singer has continuously executed looks that leave her supporters feeling satisfied and inspired. Here, you won't see some of her music video looks like her iconic latex red jumpsuit in the "Oops!... I Did It Again" visual that has inspired an undeniably nostalgic Britney Spears Halloween costume or the trendsetting nude bodysuit she rocked in "Toxic." Instead, we take a stroll through memory lane to study some of her most eye-catching outfits we would still wear today.

Starting off with the year before the millennia, Britney Spears walked the red carpet at the 1999 MTV Video Music Awards wearing not one or two, but three different looks (via Us Weekly). 

Before the event started, she sported an all-black ensemble with a powder blue-based smokey eye to match. Spears, who was just 18 at the time, wore an open duster that draped down to her feet strappy, open toe sandals (via Footwear News). The polka dot top featured feather trim around the chest and sleeves, with complementing black pants, which just scream 1999.

By the year 2000, Britney Spears had released her sophomore album, "Oops!... I Did It Again," and was picking up awards left and right. 

At the American Music Awards that same year, she took home the trophy for Favorite Pop/Rock New Artist, wearing an embellished grey jumpsuit (via E! Online). The piece was complete with a plunging neckline that stopped right below her navel, with decorated jewels around the collar to draw the eye to her toned, dancer torso. This was just the beginning of some of her best red carpet moments yet.

Two years after her win at the American Music Awards, Britney Spears attended the 2002 Grammys, where she presented alongside "Friends" star Matthew Perry. 

Embodying the phrase, "The bigger the hair, the closer to God," Spears spiced up her usual straight, blonde locks for voluminous curly tendrils that draped down her back. She stunned in a fitted red gown with an open back, and nearly 20 years later, Spears took to Instagram to revisit that moment: "It's taken me 19 years to realize that I was Julia Roberts in 'Pretty Woman,'" she penned in the caption.

Ah, we miss short-lived movie star Britney Spears. 2002 was a big year for her, as she was taking the world by storm with her music career, while getting back to her acting roots by starring in the coming-of-age film, "Crossroads."

At the premiere, she strutted the red carpet with her famous then-boo thang, Justin Timberlake, who she most definitely up-shined in her casual, stylish Y2K fit (via Entertainment Weekly). But seriously — what other era could you get away with wearing a dress and matching boots over a pair of jeans with a newsboy hat to top it off? It was a moment.

As the 2000s inched forward, the bigger Britney Spears got. 2003 was the year Spears' album "In The Zone" dropped, and subsequently one of pop culture's biggest moments of the decade occurred: the infamous kiss between her and queen of pop, Madonna, during the MTV Video Music Awards that August (via YouTube).

Just a month before that performance, though, Spears stepped out in an outfit that seemed to clap-back at critics in the media. Back in July 2003, the New York Post reported that at an MTV event, she rocked an off-the-shoulder graphic tee with tabloid Page Six's logo on the chest, but instead it reads "Page Six Six Six." The Post writes that Spears began to exhibit "bad behavior," bringing the lyric of, "I'm not that innocent" to fruition in her real-life image. At the time, she was just 22, and we merely call that growing up.

2004 was the year "Toxic" blasted on our boomboxes and car speakers, hitting the No. 9 spot on Billboard's Hot 100 in March 2004 (via Twitter). Earlier that year, Spears appeared at France's NRJ Awards, where she performed the hit single, per YouTube. But before she killed her performance, she stunned on the red carpet in Cannes in one of her most glamorous, Hollywood looks thus far.

The 5'4" singer, per Celeb Health Magazine, wore a fringe, gold beaded Roberto Cavalli mini-dress that shimmered with every step, accentuating her signature golden blonde locks (via Instagram).

While we know 2007 was a trying year for Britney Spears, as it changed the trajectory of her life, she returned to MTV's VMAs in 2008 with a graceful vengeance.

Winning best female video, pop video, and video of the year for "Piece of Me," Spears had the final laugh after performing "Gimme More" at the 2007 awards with overwhelmingly harsh reviews (via Billboard). 

She swept up multiple "Moonman" statuettes sporting an above-the-knee and glistening Atelier Versace dress, looking happier than ever, according to Just Jared. 

Nearly a decade before Britney Spears and Elton John collaborated on the "Tiny Dancer" remix, "Hold Me Closer," Spears attended the British star's annual AIDS Foundation Academy Awards Viewing Party in 2013 (per Just Jared).

Spears stepped out on the red carpet wearing a Michael Cinco Couture long, black sequined gown, and swapped out her iconic blonde hair for a highlighted chocolate brown mane that gave a more mature, sophisticated look. It was one of the few times we've seen Spears as brunette, and she didn't disappoint.

Each year Britney Spears attends MTV's Video Music Awards, she only seems to be getting better with age.

Presenting at the 2015 show, Spears channeled her mid-2000s mini-dress looks, clad in a hugging silver and gold sequined Labourjoisie dress (via HuffPost). She polished off the look with a sleek high ponytail with the ends in a dipped pastel-colored ombré. It seems like life was imitating art, as her song "Pretty Girls" featuring Iggy Azalea came out the same year. 

And just like that, Britney Spears was back at the 2016 MTV Awards changing up her style once again. The then-34-year-old hit the red carpet of the event before she performed at the awards show for the first time since her highly-publicized 2007 performance. 

Before hitting the stage alongside rapper G-Eazy, Spears rocked a classic little black dress with a twist. Getting back to her roots (literally) with her long, luscious blonde hair, Spears' mane draped over the black gown, that had an asymmetrical cut. The Julien MacDonald dress covered one sleeve and left one exposed, while revealing just the right amount of leg, fit for a (pop) queen (via Hollywood Life).

Last but not least, our last favorite Britney Spears outfit was in 2016 when the "Slumber Party" singer hit the Billboard Music Awards wearing not one, but two red carpet outfits, with the latter being our pick.

After performing a medley of some of her greatest hits and receiving the Millennium Award on behalf of her monumental moment, Spears showed off her accolade with a breathtaking look fit for the occasion. Spears sparkled in a custom Charbel Zoe Couture dress that twinkled in iridescent pastel blue, while the cutout revealed her dancer abs, per Fashion Bomb Daily. 

Since her conservatorship officially ended, Spears has been keeping a relatively low profile as far as red carpet appearances go, so until then, our fingers are crossed to hopefully witness another showstopping ensemble that is just waiting to be celebrated.