![OK Logo](https://okmagazine.com/ok_logo_black_small.png)
27 Photos That Portray Britney Spears' Unforgettable Fashion Evolution
![Britney Spears 22](https://media.okmagazine.com/brand-img/YWJtVFtTj/480x251/2013/12/britney-spears-22.jpg?position=top 480w, https://media.okmagazine.com/brand-img/YWJtVFtTj/640x335/2013/12/britney-spears-22.jpg?position=top 640w, https://media.okmagazine.com/brand-img/YWJtVFtTj/768x402/2013/12/britney-spears-22.jpg?position=top 768w, https://media.okmagazine.com/brand-img/YWJtVFtTj/1024x536/2013/12/britney-spears-22.jpg?position=top 1024w, https://media.okmagazine.com/brand-img/YWJtVFtTj/1280x670/2013/12/britney-spears-22.jpg?position=top 1280w, https://media.okmagazine.com/brand-img/YWJtVFtTj/1440x753/2013/12/britney-spears-22.jpg?position=top 1440w, https://media.okmagazine.com/brand-img/YWJtVFtTj/1600x837/2013/12/britney-spears-22.jpg?position=top 1600w, https://media.okmagazine.com/brand-img/YWJtVFtTj/2160x1130/2013/12/britney-spears-22.jpg?position=top 2160w)
Crop tops (jackets and more), hot pink vinyl, and fringe are just a few of the landmark features in birthday girl Britney Spears' fashion evolution. Prepare for 27 outfits—including that sequined loungepant moment—that portray the celeb's shocking and memorable fashion evolution.
Britney Spears in '99
![Britney Spears 1](https://media.okmagazine.com/brand-img/hGhmmCwRE/315x500/2013/12/britney-spears-1.jpg 315w)
'99 did us proud, did it not? Here, Britney Spears is celebrating her "Baby One More Time" single, but looking back at the snapshot, we're celebrating the fact that she's wearing the equiv. of sequined pajama bottoms.
Britney Spears
![Britney Spears 2](https://media.okmagazine.com/brand-img/PqySapl3e/305x500/2013/12/britney-spears-2.jpg 305w)
How do you make a pink vinyl crop top matchy-matchy? Knee-pads.
Britney Spears
![Britney Spears 3](https://media.okmagazine.com/brand-img/FMxKKdnHG/323x499/2013/12/britney-spears-3.jpg 323w)
In September of '99, our girl Brit kept up the crop top fever (before Miley, we might add) and added even more oomph with glittery slacks.... Like you didn't own a pair...
Britney Spears
![Britney Spears 4](https://media.okmagazine.com/brand-img/I3E_QdWiN/292x500/2013/12/britney-spears-4.jpg 292w)
In 1999, Brit was named the Female Artist of the Year. She accepted her award in a baby pink spaghetti strap frock—AKA, the dress you probably wanted to wear to prom.
Britney Spears
![Britney Spears 5](https://media.okmagazine.com/brand-img/XSuzxqMLj/351x500/2013/12/britney-spears-5.jpg 351w)
Britney Spears showed up to the 2000 Teen Choice Awards in an ensemble that screams "change of the century." That, of course, would be a massive amount of pink fringe and strappy sandals that show off the ankles.
Britney Spears
![Britney Spears 6](https://media.okmagazine.com/brand-img/cNGMCKSir/222x499/2013/12/britney-spears-6.jpg 222w)
Va va voom, Brit! She rocked a little sex appeal to the MTV VMAs (before the Madonna moment) with a LBD (long black dress) with a majorly high slit.
Britney Spears
![Britney Spears 7](https://media.okmagazine.com/brand-img/7OnSsXCHM/333x500/2013/12/britney-spears-7.jpg 333w)
You had a dress like this, right?
Britney Spears
![Britney Spears 8](https://media.okmagazine.com/brand-img/4Xt7Jv1fJ/289x499/2013/12/britney-spears-8.jpg 289w)
Changing up the typical crop top (and simultaneously making the ensemble much, much more '00) Britney rocked a lacy bustier with a choker necklace and crimped hair.
Britney Spears
![Britney Spears 9](https://media.okmagazine.com/brand-img/pWMW1zIgg/333x500/2013/12/britney-spears-9.jpg 333w)
When it's too chilly for a tummy-baring top, you just wear a ruched and cropped jacket. Duh.
Britney Spears
![Britney Spears 10](https://media.okmagazine.com/brand-img/MzjKcTXaF/333x500/2013/12/britney-spears-10.jpg 333w)
If you remember correctly, Brit was a particular fan of the newsboy cap.
Britney Spears
![Britney Spears 11](https://media.okmagazine.com/brand-img/JsVlyS66l/480x356/2013/12/britney-spears-11.jpg 480w, https://media.okmagazine.com/brand-img/JsVlyS66l/640x475/2013/12/britney-spears-11.jpg 640w, https://media.okmagazine.com/brand-img/JsVlyS66l/768x570/2013/12/britney-spears-11.jpg 768w, https://media.okmagazine.com/brand-img/JsVlyS66l/1024x760/2013/12/britney-spears-11.jpg 1024w, https://media.okmagazine.com/brand-img/JsVlyS66l/1280x950/2013/12/britney-spears-11.jpg 1280w, https://media.okmagazine.com/brand-img/JsVlyS66l/1440x1068/2013/12/britney-spears-11.jpg 1440w, https://media.okmagazine.com/brand-img/JsVlyS66l/1600x1187/2013/12/britney-spears-11.jpg 1600w, https://media.okmagazine.com/brand-img/JsVlyS66l/2160x1602/2013/12/britney-spears-11.jpg 2160w)
She even wore the hat on red carpet dates with JT.
Britney Spears
![Britney Spears 12](https://media.okmagazine.com/brand-img/BKtXK6-zR/329x500/2013/12/britney-spears-12.jpg 329w)
Britney Spears dressed up for her Crossroads premiere in a lacy bustier and a black newsboy cap.
Britney Spears
![Britney Spears 13](https://media.okmagazine.com/brand-img/VpmtOdWil/349x500/2013/12/britney-spears-13.jpg 349w)
It may remind you of Tinkerbell, but this dress she wore to the AMAs show in '03 is kind of adorable.
Britney Spears
![Britney Spears 14](https://media.okmagazine.com/brand-img/Xgdt3H1wU/320x500/2013/12/britney-spears-14.jpg 320w)
Take a moment to remember the velour tracksuit and how you, Brit, and Sophia Bush's character on One Tree Hill loved them so.
Britney Spears
![Britney Spears 15](https://media.okmagazine.com/brand-img/2bC6keuFo/288x500/2013/12/britney-spears-15.jpg 288w)
By now, you probably get the trend that Brit was going for.
Britney Spears
![Britney Spears 16](https://media.okmagazine.com/brand-img/2a5yGieTQ/323x500/2013/12/britney-spears-16.jpg 323w)
See above for the most famous pink fur coat out there.
Britney Spears
![Britney Spears 17](https://media.okmagazine.com/brand-img/Wjw9gCOAT/275x499/2013/12/britney-spears-17.jpg 275w)
In 2004, Britney Spears attended the Billboard Music Awards in a green and black mini dress clad in her fave fabric—lace!
Britney Spears
![Britney Spears 18](https://media.okmagazine.com/brand-img/QLJzaYyS5/319x500/2013/12/britney-spears-18.jpg 319w)
Britney Spears, KFed, and a sparkly LBD. Discuss.
Britney Spears
![Britney Spears 19](https://media.okmagazine.com/brand-img/sbZOU8_vk/281x499/2013/12/britney-spears-19.jpg 281w)
Britney Spears rocked a LWD and a fedora to an even in Las Vegas back in 2007.
Britney Spears
![Britney Spears 20](https://media.okmagazine.com/brand-img/-Ve3XdKnf/338x500/2013/12/britney-spears-20.jpg 338w)
Thought the Kardashian sisters made this silhouette famous? Please!
Britney Spears
![Britney Spears 21](https://media.okmagazine.com/brand-img/lo-Mkgulp/319x500/2013/12/britney-spears-21.jpg 319w)
Before Jennifer Lawrence owned the see-through skirt, Britney Spears flaunted the style with dark brunette locks.
Britney Spears
![Britney Spears 22](https://media.okmagazine.com/brand-img/iyIwygWlq/337x500/2013/12/britney-spears-22.jpg 337w)
So Brit's bod looks absolutely slammin' in this chartreuse bandage dress.
Britney Spears
![Britney Spears 23](https://media.okmagazine.com/brand-img/q0iCqsg_r/352x499/2013/12/britney-spears-23.jpg 352w)
You can't go wrong with an LBD, Brit!
Britney Spears
![Britney Spears 24](https://media.okmagazine.com/brand-img/I87BHMKTz/337x499/2013/12/britney-spears-24.jpg 337w)
When Britney became an X Factor judge, she gave her red carpet wardrobe a makeover with a more sophisticated lacy mini.
Britney Spears
![Britney Spears 25](https://media.okmagazine.com/brand-img/g8tyStO3U/314x500/2013/12/britney-spears-25.jpg 314w)
She even switched things up with a much-longer, but totally gorgeous hemline and a print!
Britney Spears
![Britney Spears 26](https://media.okmagazine.com/brand-img/bvIgqYvUH/307x500/2013/12/britney-spears-26.jpg 307w)
Thought one-shoulder mini dresses were totes out? Not if Britney wants to rock 'em.
Britney Spears
![Britney Spears 27](https://media.okmagazine.com/brand-img/cZs2nCIFU/332x499/2013/12/britney-spears-27.jpg 332w)
Excited for Brit's Las Vegas show? Hopefully she wears a few stunners like this!