Britney Spears Beauty Evolution: 13 Years, One Hot Mess

Posted by , on April 1, 2011 at 2:43 pm
Britney really did look "that innocent" at Z100's 5th Annual Jingle Ball back in 1998. This is obviously before her label created the sexy pop princess persona we've all grown to love.
Get a good look, because this is the last time Britney will successfully be able to pull off dark here. Little did we know at the time that the next time she goes brunette will be in the midst of a breakdown.
Apparently Brit thought she was getting ready for prom when she got done up for  the 1999 MTV Europe Music Awards.
This is what I fondly like to refer to as her glory days. When I think of classic Britney Spears, this is the image that comes to mind.
Britney went all out for the 2000 MTV Video Music Awards. I'll excuse the crimped hair for the mere fact that it was the year 2000. But the fact that she decided to mix the crimps with a few randomly [...]
Britney went all out for the 2000 MTV Video Music Awards. I'll excuse the crimped hair for the mere fact that it was the year 2000. But the fact that she decided to mix the crimps with a few randomly placed soft curls is just weird.
She must have learned her lesson because she did a much better job a year later at the 2001 MTV Video Music Awards, opting for a full head of sexy curls. FYI: we are now entering Britney's over-sexed pop [...]
She must have learned her lesson because she did a much better job a year later at the 2001 MTV Video Music Awards, opting for a full head of sexy curls. FYI: we are now entering Britney's over-sexed pop star phase... maybe my favorite one of all.
I don't know what happened to her at the 2002 Grammy Awards, but that hair is all kinds of scary. But if I must think of something nice to say, I guess I don't hate that mauve lip gloss...
Yes, this happened.
I guess if she's going to insist on having a bob, then this is the proper way to do it. Britney actually looks very soft and ladylike, fitting for a 2003 kid's charity auction event.
Obviously that understated look couldn't last forever. Britney sexed things up again for the 2004 NRJ Music Awards. This is one of my all-time favorite shades of Britney blonde. My only complaint: she [...]
Obviously that understated look couldn't last forever. Britney sexed things up again for the 2004 NRJ Music Awards. This is one of my all-time favorite shades of Britney blonde. My only complaint: she went a little heavy on the under-eye concealer, no?
And then she started rolling out the babies! Sadly, Britney's one of those people who doesn't get all glowy and beautiful during pregnancy. But she didn't look half bad at the 2005 Charlie and the [...]
And then she started rolling out the babies! Sadly, Britney's one of those people who doesn't get all glowy and beautiful during pregnancy. But she didn't look half bad at the 2005 Charlie and the Chocolate Factory premiere. 
It's officially decided – Brit is at her best when she isn't trying too hard.
Britney shocked us all in the summer of 2006, when she decided that harsh dark hair would be a good look on her. I'm still puzzled by this...
This was at the height of Britney Spears' crazy period, pictured here in late 2006, just months before the infamous head shave. You can almost see it in her eyes.
And here she is attending New York Fashion Week in 2007, less than two weeks before she shaved her head and things really went to sh*t.
Hold on tight! Things are going to take an even bigger turn for the worst before they begin to get better. Those extension are really killing me – I just don't understand...
I warned you! Brit Brit looked all kinds of tore up at Christian Audigier's 50th Birthday Bash in 2008. But don't worry, this is rock bottom.
What can I say? The girl knows how to make a comeback. By September 2008, Britney was looking like her old self again – circa 2001.
This shade of blonde is a little to platinum for my taste, but look how happy she looks arriving at the 2009 Teen Choice Awards.
She went brunette again for a minute in early 2010, but it's still much better than the dark hair debacle of 2005.
And she's officially back! We've been seeing a lot of Britney lately, as she promotes her latest album Femme Fatale. Not only is she back to blonde, but it looks like she's finally found someone who [...]
And she's officially back! We've been seeing a lot of Britney lately, as she promotes her latest album Femme Fatale. Not only is she back to blonde, but it looks like she's finally found someone who knows how to put in hair extensions. Bravo Britney – it has been quite a ride.
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Ok that title may be a little harsh it wasn’t all bad, but going through 13 years of Britney Spears photos was kinda like going on a really bumpy roller coaster ride. I’m still a little dizzy from it. She had her ups and downs, with a trajectory that looks a little something like this: a fresh-faced teen sensation turns over-sexed blonde pop star, then there was that very unfortunate brunette phase, we can just gloss right over the bald thing, which lead to some of the worst hair extensions I’ve ever seen, only to find her way back to being an over-sexed blonde pop star. Oh, don’t forget to factor in about 17 comebacks in between.

But say what you will about Britney, the girl’s a survivor, which is why we thought it was only fitting that she be the subject of StyleCaster’s latest beauty evolution. So fasten your seatbelts and click through for 13 years of Britney Spears beauty.

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  1. Sarah G says:
    April 2, 2011 at 9:18 am

    I honestly am baffled as to where she put her nipples in number 11??? Did they sew them back on in the wrong place do you think??!

    Reply