Since she exploded onto the music scene in 1998, Britney Spears has become a pro at turning heads on red carpets, as well as concert stages. Whether she was dolled up for an awards ceremony, or dressed down for a Starbucks run, what Britney was wearing became almost as celebrated and scrutinized as the hits she sang. While we wait to see what outrageous outfits Britney brings out of the closet during the promotion of her next album, let's look back at some of the most iconic and controversial fashion choices the Princess of Pop has made over the years.
Britney Spears initiated her fashion ...
Britney Spears initiated her fashion career with the iconic naughty school-girl number from the 1999 video, "...Baby One More Time." The song cemented the teenager from Louisiana as a mega-popstar.
Brit was no newbie to childhood celeb...
Brit was no newbie to childhood celebdom after her brief stint on the Mickey Mouse Club. When she appeared on the carpet for the 1999 Teen Choice Awards, her persona was pretty in pink.
Pretty Pink swung to sexy as the succ...
Pretty Pink swung to sexy as the success of the 'Baby' video took off. Britney cut her bangs, got rid of her jean skirts and introduced the belly-shirt as a staple in her wardrobe.
At the 2000 Grammy Awards, Britney wo...
At the 2000 Grammy Awards, Britney wore a shear, embellished bodysuit at her stage rehearsals for the Grammy Awards- a fundamental item during all succeeding tours for Spears.
On the 2000 Red Carpet at the Grammy ...
On the 2000 Red Carpet at the Grammy Awards, Spears aligned herself with the likes of Madonna and Marilyn Monroe with a white gown and muff combo. Madonna famously attended the Grammy Awards with Michael Jackson in 1991, wearing an almost identical outfit.
During the 2000 Grammy show performan...
During the 2000 Grammy show performance Britney wore one of her first infamous items- a pastel prom dress with foliage in gauze. Although the dress screamed pop-princess, it was a jumble of mesh, sequins and an always unfortunate turtleneck.
Britney has always had a propensity f...
Britney has always had a propensity for cowboy boots, but a floral sundress, neon pink cowboy hat, and dirty cream boots? This unflattering outfit seemed inappropriate on the Today Show in 2000.
This nude bodysuit became one of Brit...
This nude bodysuit became one of Britney's most celebrated fashion choices. At the 2000 VMAS, Britney's conservative black suit was ripped-off halfway through the performance revealing this flesh-colored number and killer dance routine.
At the 2000 Billboard Music Awards, B...
At the 2000 Billboard Music Awards, Britney chose to dress like a pimp from the 1970's. The psychedelic color scheme of this ill-fitting coat and fuzzy-hat combo was definitely noticeable... not in a good way.
Spears admitted that she was dating *...
Spears admitted that she was dating *NSYNC member Justin Timberlake in 2000, prompting a slew of matching red carpet appearances together. Wearing a tight gown of randomly assembled jean-parts, Spears looks like a cowboy debutant at the 2001 American Music Awards.
At the 2001 Superbowl, Spears perform...
At the 2001 Superbowl, Spears performed with Aerosmith wearing an assortment of semi-athletic items: a softball tube-sock, pseudo football pants, and an Aerosmith belly-shirt. This is the Britney we love to see: washboard out, hair bedroom'd up.
At the 2001 VMAS Britney performed he...
At the 2001 VMAS Britney performed her single "I'm a Slave 4 U" fully outfitted with a caravan of semi-circus folk and an albino snake. Although her belly-dancing bikini was undeniably flattering, it was a tad excessive.
The 2002 VMAS became one of Brit's bi...
The 2002 VMAS became one of Brit's biggest fashion moments. Britney arrived on the red carpet in this full-out dominatrix number. This was a confusing assortment of leather, Spartacus heels and lace. She will whip you...softly?
Although velor jumpsuits were quite t...
Although velor jumpsuits were quite the LA craze in the early 00s, we shudder when remembering them. Britney shops solo in Calypso on Valentine's Day in 2003.
At the 2003 MTV Bash, Spears poked fu...
At the 2003 MTV Bash, Spears poked fun at her pop-culture status by becoming a literal piece of pop-culture. Splaying The New York Post's infamous gossip column across her chest and wearing Roy Lichtenfeld's iconic pop-art portraits in legging-form hinted at the reverse fact: the she would be all over Page Six.
In another cheeky nod to Madonna and ...
In another cheeky nod to Madonna and 'Like a Virgin', Britney flaunts this corset-dress after downsizing from a bridal gown at the 2003 VMAS. This outfit went down in infamy due to her provocative kiss with Madge earlier in the evening.
At the NFL Kickoff in 2003, Britney w...
At the NFL Kickoff in 2003, Britney wears shrunken P.E shorts with a halter crop-top. Although her body looks fabulous, she might have been mistaken as a boot-camp instructor.
At the 14th Annual Glamour Women of t...
At the 14th Annual Glamour Women of the Year awards in 2003, Britney makes an attempt at vintage Hollywood with this LBD, gloves and British-royalty headgear.
Spears performs on TRL's 'Brand Spank...
Spears performs on TRL's 'Brand Spanking New' in chaps and a seemingly revelatory crop-top. Although her washboard is fabulous, this outfit is a haphazard mess of pleather and stretched fringe.
Sporting a look similar to recent Fer...
Sporting a look similar to recent Fergie and Gaga outfits, Spears performs at the American Music Awards in a space-age bustier and pleather boy-shorts. Unfortunately, the thigh-highs and the metallic shrug overwhelm the look.
In one of Britney's more flattering l...
In one of Britney's more flattering looks, the singer arrives at the 2004 Billboard Music Awards wearing a nude mini-dress with sheer black lace. Her accessories are sparse- only Kevin and her miniature pup interfere with the outfit.
Britney apparently spent a day at the...
Britney apparently spent a day at the beach and forgot to change during the TRL awards in 2003. This 'Blue Lagoon' look is the most comfortable Britney has seemed in her clothes.
Spears is fully pregnant in the summe...
Spears is fully pregnant in the summer of 2005 at the 'Charlie and Chocolate Factory' premiere in Los Angeles. Although Spears is peppy about the pregnancy (her shirt say "I have the golden ticket", with an arrow pointing to her stomach) one should never wear silk combined with a wife-beater.
Just over a year later, Spears is onc...
Just over a year later, Spears is once again pregnant with her second child at the 2006 Teen Choice Awards. We approve of the black locks, but that halter dress was not made to hold a pregnant woman.
2007 was the year of the infamous Bri...
2007 was the year of the infamous Britney Breakdown. From shaving her head to making odd friends (Paris Hilton?) to losing custody of her children, Britney was in a catastrophic state after her breakup with Kevin Federline. In an attempt to re-socialize, Brit hits South Beach in May wearing a black bikini and chaotic cover-up with heels.
At the 2007 VMAS Britney makes a come...
At the 2007 VMAS Britney makes a comeback. Looking rather sedated and nervous, Britney performed in a sequined black bikini and boots. We applaud her fantastic physique for a mother of two, even though the performance wasn't too inpsired.
Brit appears at the 2008 VMAS wearing...
Brit appears at the 2008 VMAS wearing a surprisingly tasteful silver dress. The neckline and length is flattering on her body; the dress combined with minimal amount of accessories is more elegant than usual.
During her 2009 'Circus' tour, Britne...
During her 2009 'Circus' tour, Britney wore a variety of circus-inspired, ring-leader outfits. Although the cut of the unisuit is cute, the sequin-illusion of pasties and underwear makes Brit look like a blow-up doll.
If Los Angeles really is that warm, i...
If Los Angeles really is that warm, it seems unnecessary to wear winter boots with mini jorts and a crop-top?
Britney's most recent look at the 201...
Britney's most recent look at the 2010 Grammy Awards took bodysuit + lace to an unfortunate level. Although the dress is Dolce & Gabbana, it's a tad revelatory for the buxom brunette.
Britney Spears gives an award to US singer Madonna during the NRJ awards ceremony, Saturday, Jan. 24, 2004, in Cannes, France.