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Celebrity

9 Really Rich Celebrities Who Dress Like They Don't Have Money

September 29, 2015 by SheFinds
shefinds | Celebrity
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We all have days when we just want to wear our comfiest, most oversized clothing and don't really care what anyone thinks. However, when a celebrity chooses to do this, they are likely to be snapped by the paparazzi and called a hobo by the media. Here are nine famous people who this happened to.

[Photos: Splash News]
Image from SHEfinds

Madonna

Madonna can wear whatever she wants because, well, b*tch, she's Madonna!

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Johnny Depp

Johnny Depp, is that you?? Barely recognized this stud under all those clothes.

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Mary-Kate Olsen

The caption of this photo is literally "Mary-Kate Olsen dresses in what looks like a blanket."

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Jaden Smith

How cute are Jaden Smith and his girlfriend?? That shirt, not so much.

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Helena Bonham Carter

Helena Bonham Carter's daily outfits include layers on layers on layers.

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Courtney Love

Courtney Love, also a fan of wearing everything in her closet all at once.

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Jared Leto

We're guessing Jared Leto was trying to disguise himself in NYC because there is no other explanation for this, ahem, interesting look.

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Nick Nolte

Nick Nolte always wears oversized clothing. ALWAYS.

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Kesha

In the days before Kesha dropped the "$" in her name, she wore tights with holes often.

 

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Jennifer Lopez in Defaience at American Music Awards 2025.
Vittoria Ceretti and Leonardo DiCaprio together at an event.
Emma Stone at the Annual Actor Awards ceremony.
Salma Hayek at the 12th Annual Breakthrough Prize Ceremony.
Kate Middleton at a formal state visit event.
Ariana Grande at the Golden Globes red carpet.
Kylie Jenner showcasing Met Gala 2025 black style.
Taylor Swift and Travis Kelce at a public event.
Ivanka Trump and Jared Kushner posing together.
Brad Pitt and Ines De Ramon at F1 premiere.
Bad Bunny performing at the Grammy Awards.
Angelina Jolie receiving the Trophee Chopard Award.
Selena Gomez at the Rare Impact Fund Benefit.
Brad Pitt and Ines De Ramon at F1 premiere.
Queen Camilla with Prince Harry and Meghan Markle.
Travis Kelce and Taylor Swift at a game.
Barack and Michelle Obama with Malia and Sasha.
Britney Spears at the Hollywood Beauty Awards.