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The Daily Dish Beauty

Britney Spears' Style Evolution: The Looks You Can't Forget

Denim, diamonds, and snakes, oh my!

By Tamara Palmer

Britney Spears has morphed from a (not that) innocent school girl to saucy mother of two over her 18-year pop music career. Her trajectory to pop icon has been full of memorable outfits that have probably been permanently seared into your brain — that denim dress, anyone? It's been a wild ride, y'all, and in honor of the star's latest album Glory, which drops today, let's relive some of Britney's most magical visual moments, baby, one more time. . . 


When we first met our dear Britney Jean, she looked like this: All-American and sporty, with just a slightly naughty twist. At that time, no one knew that baring her midriff in a school uniform would be just the tip of the iceberg.


Mattel picked up on what Britney was putting down, creating a sassy doll for her in 1999. She spent most of that year with minimal makeup until David LaChapelle got a hold of her for a Rolling Stone "Teen Queen" cover story. Suddenly, she looked not that innocent.


And then she hit the VMAs in 2000, strolling down a staircase in a suit and stripping down to a skimpy nude bra top and bikini-esque pants by David Dalrymple, designer of Patricia Field's House of Field line. Racy Britney was born!


She stepped out the next year in two of her most memorable outfits of all time. A floor length strapless denim concoction that matched her then-boyfriend Justin Timberlake has still seen no designer claiming credit, but it's become one of the most notorious couple fashion moments in history. She also wore a festive two-piece accented by a boldly slithering fashion accessory for the VMAs, her favorite place to dress outrageously.


She donned a full-on dominatrix look at the next VMAs, where she presented Michael Jackson with a Video Vanguard award.


She channeled Like a Virgin Madonna for that notorious VMAs smooch, totally upstaging Christina Aguilera in the process. She then slipped into a space age sexy flight attendant outfit designed by Jeremy Scott for her 2003 "Toxic" video.


The Kevin Federline years, brief but intense, were marked by Britney breaking free to be her most casually styled self, from trucker caps and patchwork hats to cheeky maternity tees. 


It was a tumultuous and uncertain time after splitting with her husband, shaving her head and hoping for a fresh start. Blonde extensions came back right away though, and experiments with being a brunette followed.


Britney got her mind and body back on track over the next few years as she embarked on her Circus tour and found love with her former agent Jason Trawick. You can see her confidence re-emerging as well, for it takes cojones to show up to the Grammys basically bottomless.


Britney kept us glued to the boob tube for her X Factor judging stint in 2012, putting Simon Cowell in his place while looking fresh, fun and flirty.


After she helped new stars like Fifth Harmony on The X Factor, it was time to get back in the studio, get super-toned and "Work, B**ch!"


She glowed in off-the-shoulder Mikael D dress at the 2014 People's Choice Awards, wowing onlookers with an unexpectedly prim, classic look.


Britney's in unbelievable shape today, which makes the job of her designers pretty easy. She's rocking sophisticated lingerie looks in her new video "Make Me. . . " and Mark Zunino, who crafted her intricate, hand-beaded red costume for the 2016 Billboard Awards, told ET that "Britney's body is so toned that we were able to forgo using nude illusion and were able to have hand draped crystals swaged on her actual body."

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