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Lady Gaga -

If anyone was going to wear these Alexander McQueen Armadillo shoes, it would be Gaga. She did so at the 2010 VMAs.

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Katy Perry -

Why play 'Where's Waldo?' when you can play 'Where's Katy Perry's Pinky Toe?'

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Britney Spears -

The singer is pictured wearing what can only be described as a pair of torture devices, this at the 4th Annual Hollywood Beauty Awards in LA.

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Sandra Bullock -

Peep-toe shoes are great, but this pair the actress wore to the London premiere of 'Gravity' in 2013 look painful.

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Taylor Schilling -

How hot does the 'Orange Is the New Black' star look? We mean literally. Just look at her steamy shoes—she must be boiling in them!

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Kate Moss -

As a former model, Moss is probably used to uncomfortable shoes. Maybe that's why she doesn't mind these crushing her toes.

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Julianne Moore -

Moore looked magnificent on the red carpet at the 2013 Cannes Film Festival, though her pinky toe was trying to escape her shoe!

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Rihanna -

RiRi rocked this amazing outfit at the 2017 Met Gala. But there's no way on Earth those wraps are comfortable!

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Meghan Markle -

Meghan Markle wore these shoes to her's and Prince Harry's engagement announcement photo shoot. Is it just us, or do her shoes seem a tiny bit too big for her?

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Jennifer Lawrence -

Shoes that are too big? Sweaty feet? Both are annoying, but combined they're a real problem! Jennifer Lawrence showed us why at 'The Hunger Games: Catching Fire' premiere in New York.

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Kim Kardashian -

Kim Kardashian thought it would be a good idea to wear these tight high heels with criss-cross straps while heavily pregnant. Probably not the best way to let your blood flow properly...

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Lady Gaga -

One of Gaga's most controversial outfits also included shoes wrapped in raw meat. Probably not the most breathable shoes...

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Nicki Minaj -

The rapper looks great in pink, and the same goes for her Giuseppe Zanotti peep-toe pumps. Though comfortable is probably not a word we would use to describe them.

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Rashida Jones -

We love the floral dress Jones wore to the Film Independent Spirit Awards in 2013, but the actress must have been in pain wearing those heels. Ouch!

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Heidi Klum -

The former supermodel's feet are likely beaten up from years of wearing uncomfortable shoes. This is just another pair of those.

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Sarah Paulson -

The 'American Horror Story' star probably felt the pressure to look her best at the 2018 Elle Women in Hollywood event. And it looks like her feet also felt the pressure of her shoes!

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Chrissy Teigen -

Teigen dazzled in a gold strapless dress for the Time 100 Gala in New York City. Her feet, however, were feeling the squeeze, and the rain.

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Kate Beckinsale -

The actress probably ordered her shoes one size too small and it was too late to return them before the 2014 Grammys!

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Lady Gaga -

Gaga wore these ginormous 24-inch (61 cm) platforms to the 2011 CFDA Awards. When you need someone to hold your hand while you walk, that says something about the shoes you're wearing...

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Jennifer Hudson -

The singer and actress turned heads at the 2014 People's Choice Awards. For its part, her pinky toe turned blue from poor circulation!

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Amy Adams -

The actress kept her toes as tight as she could during the 11th Annual John Varvatos Stuart House Benefit in Los Angeles.

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Madonna -

Okay, we must admit that these Chanel pistol shoes look pretty cool. They just don't look very comfortable.

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Sarah Jessica Parker -

The 'Sex and the City' actress is pictured wearing a pair of Louis Vuitton lion pumps. Surely walking like a lioness can't be comfy. 

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Britney Spears -

The singer wore these beautiful black T-strap block heels to the premiere of 'Once Upon a Time...in Hollywood' in 2019. They don't seem to fit very well, do they?

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Lady Gaga -

Gaga again! The singer is pictured leaving ABC Times Square Studios in 2013 in these extreme high heel platform boots.

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Alysia Reiner -

The 'Orange Is the New Black' actress apparently has no problem walking around with squished toes.

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Daphne Guinness -

The fashion designer is known for her bold style, and her shoes are no exception. How can one walk in those, we wonder?

Sources: (Marie Claire)

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