The 50 Most Shocking Celebrity Style Moments On And Off The Red Carpet

Posted by , on May 26, 2012 at 1:30 pm

Lady Gaga sporting quite the headgear.

Rihanna attends a photocall for Battleship at The Corinthia Hotel. Definitely shocking to see her blonde locks!

Crazy to see the late Amy Winehouse dressed so.. business-like?

Jessica Simpson arrives to the NBC Universal 2012 Winter TCA Tour All-Star Party. Shocking to see her pregnant, or beyond pregnant we should say.

Willow Smith arrives at the premiere of Sundance Selects' First Position. Two things here: Willow is all grown up and it's weird! And, her hair? Quite the switch she made.

Singer Kesha arrives at the 2010 American Music Awards. Her crazy attire shocked the red carpet.

Lindsay Vincent from Cumbria dresses as Lady Gaga during the MCM London Comic Con convention at the ExCel Centre in East London.

I know her album is called Pink Friday, but holy pink! It's a Pepto-Bismol shock.

Winona Ryder speaks at the Black Swan press conference during the 2010 Toronto International Film Festival. She looks like she got dressed in a mix between her father's closet and Goodwill. Definitely a [...]

Winona Ryder speaks at the Black Swan press conference during the 2010 Toronto International Film Festival. She looks like she got dressed in a mix between her father's closet and Goodwill. Definitely a shock from such a beautiful woman!

Rihanna performs at The Brit Awards 2012. Not only is she blonde now, but she has a fro going on.

Lady Gaga speaks onstage during the 2011 MTV Video Music Awards. Quite a shock seeing Gaga dressed and looking completely like a man.

Lindsay Lohan isn't typically the classiest dresser, so this was a shock to us. Although she tried, the bleached hair with the pale skin and the white suit really makes her transparent.

Dakota Fanning is all grown up. Where did the time go? It feels like just yesterday she was playing the little girl in Uptown Girls! Now she's posing on the cover of Cosmo.

Keke Palmer goes rock climbing? The things we find out.

This handsome young man sure grew up quickly. A miniature Will Smith!

A waxwork model of Barbadian R&B singer Rihanna is unveiled at Madame Tussauds museum. Not only is it a fro this time, but it's red! Oh Rihanna..

Courtney Love might have momentarily lost her marbles. Her style followed suit. I guess this isn't too shocking.

Madonna shocked the world as she took the stage for her Blond Ambition tour in this Jean Paul Gaultier corset.

We all love Whitney Houston and the crazy outfits she wore onstage. She never let the crowd be bored.

Nicki Minaj visits BET's 106 & Park along with her green 'do.

That's a cape dress.

British actor Sacha Baron Cohen dressed as Admiral General Aladeen poses to promote the film, The Dictator.

Adrienne Bailon attends New York Fashion Week in a gold number.

Lady Gaga wears her controversial meat dress.

Blake Lively attends the Gossip Girl 100 episode with a major neckline moment.

Elizabeth Hurley stole the show at the premiere of Four Weddings and a Funeral, when she wore this Versace safety pin dress!
Spice Girls... need I say more?
Katy Perry finally got rid of that god-awful blue hair and opted for luxurious purple hair. We love this dark dye-job.

Britney Spears and Rihanna smack lips during the 2011 Billboard Music Awards.

...Bjork...

Cher poses in her S&M attire.

Gwyneth Paltrow rocks her mermaid gown.

Nicki Minaj again... sigh.

Race car driver Danica Patrick gets dolled up.

Pop star Britney Spears goes to the extreme in her new music video as she teams up with Snoop Dogg. Britney went for it in flashing the crowd with her performance with Snoop Dogg.

Lindsay Lohan goes blonde. Red-headed little girl from The Parent Trap went bleached blonde!

Nicole Richie said goodbye to the messy party-girl to sophisticated fashion muse.

Miley Cyrus shows a whole lot of side boob.

Justin Bieber... we're still waiting for him to wear clothes that fit.

Paris Hilton performs. Yep, that happened.

Hugh Hefner and revolving girlfriends who somehow always manage to match, kind of.

Britney rocked her sequined nude number, yet again not leaving anything for us to imagine.

Wedding dresses, Madonna and a girl kiss.

Lil' Kim in her pink hair and boots to match.

Kimberly Stewart going for it at Joey and T fashion show in the early 2000s.

Mary-Kate Olsen surprised everyone with her slim frame as they received their star on the Hollywood Walk of Fame.

P. Diddy at his all-white party.

Michael Jackson and his white glove.

Kim Kardashian and Kanye West complement each other perfectly.

Lizzy Gardiner in her American Express Gold Card dress.

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It seems like the world is never short of another crazy. We secretly love watching some of celebs show their more human side (read: watch them make some major fashion failures). With avant garde and directional fashion designers, obviously celebs and their stylists have a lot to consider when it comes to a red carpet dress, hairstyle or overall moment.

As much as we love when risks are taken, we love even more when they fall a little short or are so out there we have to seriously ponder what (or if) they were thinking. With singers like Lady Gaga rocking dresses made out of her dinner and Katy Perry sporting every color of the rainbow on top of her head, there are continuously new surprises. In gushing over some of our favorite moments in the office, I couldn’t help but round up the best of the best cray cray mo’s we could recall, that were caught on and off the red carpet.

Click through the slideshow above to see some of the most shocking Hollywood style moments.

What’s your top celeb style surprise? Tell us in the comments section below!


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