Style Icon: Britney Spears

Britney Spears

Britney Spears' "...Baby One More Time" music video.
Photo: Jive Records/GIF: Jenny Shafei

...Baby One More Time was the very first CD I picked out and purchased on my own, which positions me at the epicenter of a generation of young girls who looked to Britney Spears as a beacon of ~cool~ in their formative adolescent years. Before Baby, I latched on to the Spice Girls, but something about their over-the-top packaging and nicknames (and maybe also accents) kept them at arm's length—kind of like an IRL version of Jem and the Holograms. But then, Britney broke out with her video for "...Baby One More Time," and you could almost feel the reverberation of jaws dropping from coast to coast. The song alone was an instant pop classic, but coupled with her sexy schoolgirl steez, Britney's debut all but held you by the collar and screamed at you to take notice.

Britney Spears

Britney Spears' "...Baby One More Time" music video.
Photo: Jive Records/GIF: Jenny Shafei

Truth be told, I may have been too young at the time to fully comprehend the sensational Lolita vibes in this video—all I saw was a girl singing in a school that looked like mine, hanging with a basketball, and showing a lot of stomach. (Sadly, pink maribou-feather hair ties did not survive to this year's '90s reboot.) I did know that it scared the s*** out of my parents, which, as a bratty preteen, obviously made Britney infinitely more appealing.

Britney Spears

Britney Spears on the cover of "Rolling Stone" in 1999.
Photo: Rolling Stone/David LaChapelle

Then, Britney, age 17, appeared on the March 1999 cover of Rolling Stone swanned out on pink satin sheets in a black demi-cup bra and polka-dotted boyshorts, clutching a Tinky Winky Teletubby doll in one hand and a landline phone (WITH A CORD) in the other. Photographed by David LaChapelle, the shoot was meant to play up Brit's percolating teen dream status, and boyoyoy, did it. Britney: 2, parents of America: 0.

Britney Spears

Britney Spears on the set of her "Sometimes" music video in 1999.
Photo: Getty Images

In her earliest days of pop superstardom, Brit introduced one of the fashion world's most confusing articles of clothing: the short-sleeved, turtleneck crop top. It's perfect for all those times your neck and chest get cold, but your arms are sort of hot and you want to show off your abs. (If you can name one real example of a time that happens, I'll personally ship you one of these frankenshirts.) Strangely enough, they're popular again. IMHO, that's enough of an official Style Icon endorsement to drop the mic on this post right now, but selfishly, I also want to get to the other eras of Britney.

Britney Spears

Britney Spears' "Oops!...I Did It Again" music video.
Photo: Jive Records/GIF: Jenny Shafei

For the lead single off her sophomore album, Oops!...I Did It Again, Brit went for a video with a futuristic, intergalactic theme (as was SO en vogue in 2000). A wandering astronaut stumbles upon a lair rigged with pyrotechnics and falls in love with an Amazonian martian girl (Britney) in a red latex catsuit. It's a classic love story, replete with a Titanic reference. This video is also the reason I bought begged my mom to buy my first hair straightener.

Britney Spears

Britney Spears backstage at her Oops!...I Did It Again tour in 2000.
Photo: Getty Images

Technology has advanced considerably since the dawn of the new millennium, but when headset microphones were this clunky and massive, Brit stuck with them to the point of incorporating them into her style, wielding them as both accessory and necessity (just like her dangly belly-button ring!).

Britney Spears

Britney Spears performing at the 2000 MTV VMAs.
Photo: MTV/GIF: Jenny Shafei

Take, for instance, that time she stripped on live television for the 2000 MTV Video Music Awards. She started off in a baggy pinstriped suit, but soon ended up in a flesh-colored bra and bootcut pants littered with rhinestones. You barely noticed that giant black thing coming out of her head, right? OK, so that's mostly because at the time, this outfit was REALLY shocking and controversial, but the sparkly nude look has been replicated by many a pop star since, from Jennifer Lopez to Lady Gaga, as has the suggestive striptease bit (most recently courtesy of Miley Cyrus).

Britney Spears

Britney Spears performing at the 2000 MTV VMAs.
Photo: MTV/GIF: Jenny Shafei

Brit's iteration is still my favorite, and I think it's safe to say that, by now, that's true for almost everyone. (BONUS: go here to watch archival footage of Brit back in 2000, reacting to the comments of THA PEOPLE.)

Britney Spears

Britney Spears performing at the 2001 VMAs.
Photo: MTV/GIF: Jenny Shafei

It may not have become a staple accessory for Brit in quite the same way as the headset microphone, but the Burmese python (her name is Banana!) she wore around her shoulders for her 2001 VMA performance of "I'm A Slave 4 U" is almost more iconic. Point me to a 20-something lady today who didn't once mimic this performance in her bedroom with a scarf, and I'll show you a liar.

Britney Spears

Britney Spears' "Toxic" music video.
Photo: Jive Records/GIF: Jenny Shafei

Britney reprised the glittering birthday suit look in 2004 for her "Toxic" video, but this time, I'm like 99.999% sure those silver flecks are affixed to her actual skin and not a nude fabric. It's the only logical next step in an industry that demands you outdo yourself.

Britney Spears

Britney Spears' "Toxic" music video.
Photo: Jive Records/GIF: Jenny Shafei

She was several albums into her career at the time, but the "Toxic" video was the first time Brit REALLY flexed her muscles as a chameleon. Sure, she portrays two characters in "Lucky," but in THIS video she role-plays a deadly flight attendant...

Britney Spears

Britney Spears' "Toxic" music video.
Photo: Jive Records/GIF: Jenny Shafei

...and a redhead! She retained the classic Britney sexiness throughout videos for "Outrageous," "Gimme More," and "Piece Of Me," but this experimentation in "Toxic" was a precursor to the forthcoming era in which she openly embraced heavy-handed camp (long before Katy Perry started shooting whipped cream from her bra).

Britney Spears

Britney Spears on her Circus tour in 2009.
Photo: Getty Images

The best example of Brit's newly minted love of THEME is, of course, the tour that accompanied her 2008 release, Circus. Spears & co. took the big top and ran with it, with Britney vacillating effortlessly between ringleader and spectacle. Also of note: Brit's tasseled, burlesque mock-pasties, another performance look that has since been resurrected by Miley.

Britney Spears

Britney Spears' "Work B****" music video.
Photo: RCA Records/GIF: Jenny Shafei

Fast forward to today, "Work B****," and the official drop of Britney Jean. Brit is back with underwire crop tops, S&M paraphernalia, and a brand new 10-track album that echoes and encapsulates everything she's taught us to love about the glitter and spectacle of pop music over the past 15 years. Make way for the feels, y'all!

Like us on Facebook so we can be friends and follow us on Twitter @MTVstyle to talk.