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In Honor of Awards Season, 48 Times Celebrities Really Struggled with Their Fancy Clothes

Aw, Jennifer Lawrence.

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It's hard enough to last one night out without turning into Girl Using McDonald's Bags as Shoes, so imagine what it's like having to wear heels and constricting clothing night after night for months—and smiling. Yup. Here, feel for 48 celebrities whose costumes might have proved more trouble than they were worth.

1 of 48
<p>Don't just stand there, Sean Penn—*untangle* her, god.</p>
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Charlize Theron

Don't just stand there, Sean Penn—*untangle* her, god.

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2 of 48
<p>To free the nipple or not free the nipple? </p>
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Miley Cyrus

To free the nipple or not free the nipple?

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3 of 48
<p>Ah, the strapless-top shimmy. We know it well.</p>
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Kate Hudson

Ah, the strapless-top shimmy. We know it well.

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4 of 48
HOLLYWOOD, CA - FEBRUARY 24: Actress Jennifer Lawrence reacts after winning the Best Actress award for "Silver Linings Playbook" during the Oscars held at the Dolby Theatre on February 24, 2013 in Hollywood, California. (Photo by Kevin Winter/Getty Images)
Jennifer Lawrence

The realest. 

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5 of 48
<p>"What am I supposed to do with this?"</p>
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Oprah Winfrey

"What am I supposed to do with this?"

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6 of 48
<p>Smiling through the awk like a true pro.&nbsp;</p>
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Katharine McPhee

Smiling through the awk like a true pro. 

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7 of 48
LAS VEGAS - MARCH 18: Actress Katherine Heigl (L) accepts the Female Star of the Year Award after part of her dress broke during the ShoWest awards ceremony at the Paris Las Vegas during ShoWest, the official convention of the National Association of Theatre Owners, March 18, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
Katherine Heigl

When your dress breaks as you're presenting but the show must go on. 

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8 of 48
<p>"Good day, Matthew McConaughey!! I said GOOD DAY."</p>
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Kate Hudson and Matthew McConaughey

"Good day, Matthew McConaughey!! I said GOOD DAY."

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9 of 48
<p>Oh no. Do you think he left a tag on?&nbsp;</p>
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Jay-Z

Oh no. Do you think he left a tag on? 

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10 of 48
<p>Prime candidate for a Caption This.&nbsp;</p>
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Rita Ora

Prime candidate for a Caption This. 

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11 of 48
<p>Everybody, after using the bathroom.</p>
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Brad Pitt

Everybody, after using the bathroom.

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12 of 48
<p>This is why you need a fluffer. Or a husband. </p>
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Jessica Alba and Cash Warren

This is why you need a fluffer. Or a husband.

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13 of 48
<p>John Legend moonlights as one (a fluffer), little-known fact.&nbsp;</p>
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Chrissy Teigen and John Legend

John Legend moonlights as one (a fluffer), little-known fact. 

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14 of 48
<p>Stairs: 70 percent more dangerous when you've got actual lawn-chair covers sprouting from your hips.</p>
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Naomie Harris

Stairs: 70 percent more dangerous when you've got actual lawn-chair covers sprouting from your hips.

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15 of 48
<p>�</p>
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Ryan Reynolds

😥

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16 of 48
<p>"Was this there when I left the house?"</p>
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Rosamund Pike

"Was this there when I left the house?"

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17 of 48
<p>�</p>
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Sophia Bush

😅

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18 of 48
<p>�</p>
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George Clooney

😠

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19 of 48
<p>When you don't even care who sees anymore.</p>
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Jennifer Lawrence

When you don't even care who sees anymore.

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20 of 48
<p>Pictured: Reenactment of when you lose your contact on the bathroom floor. </p>
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Mary Kate and Ashley Olsen

Pictured: Reenactment of when you lose your contact on the bathroom floor.

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21 of 48
<p>An incredibly photogenic strapless shimmy.</p>
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Lea Michele

An incredibly photogenic strapless shimmy.

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22 of 48
<p>"Wait. This goes where?"</p>
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Rosario Dawson

"Wait. This goes where?"

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23 of 48
<p>Before your mom tells you what a handsome boy you are.&nbsp;</p>
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Ryan Gosling

Before your mom tells you what a handsome boy you are. 

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24 of 48
<p>"Oh, look! Lucky penny!"</p>
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Madonna

"Oh, look! Lucky penny!"

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25 of 48
<p>Make sure your wrap dress is securely fastened before waving. Trust. </p>
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Kate Middleton

Make sure your wrap dress is securely fastened before waving. Trust.

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26 of 48
<p>Mid-putting-on-jacket or scarecrow pose? We might never know.</p>
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Winona Ryder

Mid-putting-on-jacket or scarecrow pose? We might never know.

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27 of 48
Sarah Jessica Paker at the Guggenheim Museum in New York City, New York (Photo by Tom Kingston/WireImage)
Sarah Jessica Parker

😩

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28 of 48
UNIVERSAL CITY, CA - AUGUST 09: Actress Megan Fox poses with the Choice Hottie Award in the press room during the 2009 Teen Choice Awards held at Gibson Amphitheatre on August 9, 2009 in Universal City, California. (Photo by Jason Merritt/Getty Images)
Megan Fox

😜

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29 of 48
Christie Brinkley during 2005 AAFA American Image Awards to Benefit the Rita Hayworth Fund of the Alzheimers Association at The Grand Hyatt Hotel in New York City, New York, United States. (Photo by Michael Loccisano/FilmMagic)
Christie Brinkley

Ugh, don't you hate it when your sparkly heel gets stuck in your fur stole? 

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30 of 48
Singer Hilary Duff departs the Metropolitan Museum of Art Costume Institute Gala Superheroes: Fashion And Fantasy at the Metropolitan Museum of Art on May 5, 2008 in New York City. (Photo by James Devaney/WireImage)
Hilary Duff

The daintiest strapless shimmy.

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