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

Aw, Jennifer Lawrence.

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
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
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 Parker

😩

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28 of 48
Megan Fox

😜

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29 of 48
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
Hilary Duff

The daintiest strapless shimmy.

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