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It's Met Monday!! Let's Celebrate With Anna Wintour's Silliest Outfits Through The Years!

Anna Wintour has worn some weird stuff before.

Even the queen of fashion can get it wrong sometimes!

Anna Wintour keeps it very eclectic at times, which means that there are more than a handful of overly colorful and not exactly good-looking outfits in her past.

The Vogue editor is not one to play it safe, as evidenced by some of her zany prints and over-the-top coats, but she'll never, ever part from her beloved Manolo Blahnik slingbacks.

Feel better about your own fashion sense by clicking through the gallery (below)!

CLICK HERE to view "Anna Wintour's Silliest Outfits Through The Years!"

CLICK HERE to view "Anna Wintour's Silliest Outfits Through The Years!"

CLICK HERE to view "Anna Wintour's Silliest Outfits Through The Years!"

CLICK HERE to view "Anna Wintour's Silliest Outfits Through The Years!"

CLICK HERE to view "Anna Wintour's Silliest Outfits Through The Years!"

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Taylor Swift Grunges It Up In Plaid For A Visit To Anna Wintour's House

Taylor is in a grunge mood in New York.

Would you wear combat boots and a plaid dress to Anna Wintour's house, Perezcious readers???

Taylor Swift would, and did, in New York Sunday night as she was spotted entering the Vogue editor's townhouse the night before the glamorous Met Gala.

Related: Taylor Celebrates Gigi Hadid's 21st B-Day

As co-chair of the event this year, Swifty has probably been spending a lot of time with Miz Wintour, but it was a bold choice to wear this outfit.

Somehow we don't think Anna is into the whole grunge aesthetic, despite having given the New Romantics singer a rock 'n' roll makeover for the May issue.

But Tay was still a total cutie and worked the look, and it appears she's really feeling grungy lately because she was spotted in a flannel button-down and torn jeans earlier on Sunday in NYC. Inneresting!

We're dying to see her glam it up for the Met Ball tonight!

Make sure to visit PerezHilton.com for the best coverage!

[Image via Pacific Coast News Online/Splash News.]

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Anna Wintour Dishes About Taylor Swift's New Vogue Look & The Met Gala Documentary! Watch!

See Anna GUSH about Taylor!

We are totally captivated by Taylor Swift's super sexy Vogue cover!

And now, the popular publication's editor-in-chief, Anna Wintour, is opening up about the new, sultry side of the pop princess we haven't quite seen before!

Related: Taylor Is SO Over Her Feud With Kanye West!

The fashionista went on the TODAY Show on Thursday to open up about her precious partnership with the 26-year-old, saying:

"I'm thrilled that [the cover girl is] Taylor Swift, who's my co-chair this year at the Met Gala."

We wonder if this continued collaboration is the reason why TayTay adopted an Anna-esque bob! LOL! Buuuuut we digress.

The 66-year-old explained on the morning show why she went with this AH-mazing aesthetic for Swifty's cover, dishing:

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Anna Wintour Has Strict Food Demands For The Met Gala! Can You Guess What They Are?

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She doesn't have that ice queen reputation for nothing!

Anna Wintour breathed new life into Vogue magazine when she took over in 1989 as editor-in-chief, and she did the same to the Met Gala when she was handed its reins in 1995.

Related: Anna Attends Yeezy Season 3

The upcoming documentary, The First Monday in May, details the meticulous process that goes into making fashion's biggest night absolutely perfect.

You've seen the trailer, but a new New York Post interview with director Andrew Rossi, Wintour's commander-in-chief Sylvana Durett, and former events planner Stephanie Winston Wolkoff sheds further light on just how involved Wintour is.

During filming, the 66-year-old also gave Rossi a hard time once in a while:

"There were a lot of protocols to follow. There were certain times when Anna would say, ‘I'm done, I don't want to film anymore.'"

It should certainly come as no surprise that Anna's a total perfectionist. Durrett said:

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Watch The Dramatic Trailer For Met Gala Documentary The First Monday In May!

Go behind the scenes in this Met Gala documentary.

The September Issue part deux!

Vogue has just released the trailer for The First Monday In May, which documents the behind-the-scenes process of preparing for the 2015 Met Gala.

And it looks WILD!

Related: Caitlyn Jenner Talks Kim Kardashian's Met Gala Dress

Everything from getting the theme just right without being racist to finalizing the guest list to discussing Rihanna's performance budget is highlighted as organizers scramble to make fashion's biggest night a resounding success.

We usually only get to see the glamorous final result, but A LOT happens behind the curtain to make sure things go off without a hitch.

Watch for a taste of the madness (below)!

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Taylor Swift Is TOTALLY Rocking An Anna Wintour Bob On The Grammys Red Carpet — But Who Did It Better???

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The queen of Vogue and pop music royalty face-off!!

Taylor Swift glided down the Grammys red carpet rocking a fresh chop job extremely reminiscent of Anna Wintour's iconic 'do!

Seriously, fashion's most famous mug has worn this bangin' hairstyle since the beginning of her time.

While we're excited for the memes to come out of this A-list matchup, we have to ask…

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Rob Kardashian Accepts A Touching Message From Kanye West… That Was Meant For Anna Wintour

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Rob Kardashian is such a prankster!

On Friday, Kanye West decided to give a shout out to one of his biggest fans: Vogue editor-in-chief Anna Wintour!

Related: Kanye West Drops A New Song!

Not only did the fashion goddess attend the Yeezy Season 3 show at Madison Square Garden on Thursday, she's been supportive of the rapper for several years. She even put him and wife Kim Kardashian West on the cover of her famous magazine!

To show his appreciation, West wrote the following messages on Twitter:


Being the jokester that he is, Rob decided to have fun with his brother-in-law!

He wrote:


Blac Chyna's boyfriend is just kidding though. On Thursday, he posted a photo of the TLOP musician on his Instagram with the message:

"This is why I Love my Brother!!"

In the pic, Ye was wearing a shirt paying tribute to his late father Robert Kardashian.

Even with all of the drama surrounding the family, Rob still has a sense of humor.

[Image via WENN.]

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