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

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
Image: Getty

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

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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.

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

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
Image: Getty
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Where art thou hat? Thou hat, here.

2010

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
Image: Getty

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

2014

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
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Um.... what kinda fuckin’ fedora situation is this? Bad hat.

2015

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
Image: Getty
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A hat for an artiste!

2017

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
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A moody navy hat for a moody navy Brad.

2019

Illustration for article titled And Now, 10 Years of Brad Pitt’s Newsboy Cap
Image: Getty
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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.

Senior Writer, Jezebel. My debut book, LARGER THAN LIFE: A History of Boy Bands, is out now.

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DISCUSSION

garyyogurt
Gary Yogurt

These are all pictures of driving caps. Newsboy caps are floppier and made from several panels.