And Now, 10 Years of Brad Pitt’s Newsboy Cap

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Hey there, I’ve got a quick question: When did Brad Pitt start wearing a newsboy cap?

In the last, I don’t know, year or so, every photo of Pitt has included his signature flap cap headwear. (I could be wrong, but then again, you think about what Brad Pitt looks like. He’s wearing a hat in your imagination, right? Touché, motherfucker.) On Wednesday afternoon, when I stumbled upon a profile of the actor in the New York Times, I once again saw that familiar image and felt that familiar sensation: there was Brad Pitt at the top of my desktop, hatted-up.

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Naturally, I decided I must investigate this phenomenon to see how long Pitt has worn the 20th century-style hat meant for fishmongers and children who yell “Extra, extra!” in cartoons. I did what any veteran reporter would do: I searched “Brad Pitt hat” in our various photo servicing platforms and discovered he’s been rocking these caps for a literal decade, at least. So now I present to you, a decade in Pitt hats:

2009

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Where art thou hat? Thou hat, here.

2010

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Have you ever seen a happier hat? I hat not.

2014

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Um.... what kinda fuckin’ fedora situation is this? Bad hat.

2015

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A hat for an artiste!

2017

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A moody navy hat for a moody navy Brad.

2019

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The present day. Here’s Pitt’s hat befriending Leonardo DiCaprio’s sunglasses in London. What a sight to behold.


Thank you for accompanying me on this journey.

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