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.
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1 of 48
Charlize Theron
Don't just stand there, Sean Penn—*untangle* her, god.
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2 of 48
Miley Cyrus
To free the nipple or not free the nipple?
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3 of 48
Kate Hudson
Ah, the strapless-top shimmy. We know it well.
4 of 48
Jennifer Lawrence
The realest.
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5 of 48
Oprah Winfrey
"What am I supposed to do with this?"
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6 of 48
Katharine McPhee
Smiling through the awk like a true pro.
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
Kate Hudson and Matthew McConaughey
"Good day, Matthew McConaughey!! I said GOOD DAY."
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9 of 48
Jay-Z
Oh no. Do you think he left a tag on?
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10 of 48
Rita Ora
Prime candidate for a Caption This.
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11 of 48
Brad Pitt
Everybody, after using the bathroom.
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12 of 48
Jessica Alba and Cash Warren
This is why you need a fluffer. Or a husband.
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13 of 48
Chrissy Teigen and John Legend
John Legend moonlights as one (a fluffer), little-known fact.
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14 of 48
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
Ryan Reynolds
😥
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16 of 48
Rosamund Pike
"Was this there when I left the house?"
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17 of 48
Sophia Bush
😅
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18 of 48
George Clooney
😠
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19 of 48
Jennifer Lawrence
When you don't even care who sees anymore.
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20 of 48
Mary Kate and Ashley Olsen
Pictured: Reenactment of when you lose your contact on the bathroom floor.
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21 of 48
Lea Michele
An incredibly photogenic strapless shimmy.
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22 of 48
Rosario Dawson
"Wait. This goes where?"
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23 of 48
Ryan Gosling
Before your mom tells you what a handsome boy you are.
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24 of 48
Madonna
"Oh, look! Lucky penny!"
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25 of 48
Kate Middleton
Make sure your wrap dress is securely fastened before waving. Trust.
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26 of 48
Winona Ryder
Mid-putting-on-jacket or scarecrow pose? We might never know.
27 of 48
Sarah Jessica Parker
😩
28 of 48
Megan Fox
😜
29 of 48
Christie Brinkley
Ugh, don't you hate it when your sparkly heel gets stuck in your fur stole?
Maggie MaloneyAssociate Digital EditorMaggie Maloney is the associate editor at Town & Country and ELLE Decor, where she covers style, beauty, jewelry, and the many members of the royal family.
