5 Middle-Aged Men Who Dress Like Teenagers

Have you ever seen a middle-aged man in a slogan tee-shirt, hoodie or <shudder> backwards ball cap and wondered why he was still dressing like a teenager? These 5 celebrities are all guilty of borrowing adolescent style occasionally. Just for contrast, we are also showing you how great they look when they do dress like grown-ups.

By: Cynthia Nellis

May 5, 2011

Source: Getty Images

Did you ever go on a date all dressed up to find that your date thought it perfectly fine to wear jeans and sneakers? Welcome to Jennifer Aniston's world. Forty-something Adam Sandler was burning up the red carpet all over the world wearing sloppy-looking hoodies, tees and jeans. Adam is awesome, but it's time to grow up (and just wait until you see how great he looks in a suit! Keep clicking.)

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5 Middle-Aged Men Who Dress Like Teenagers

1. Adam Sandler

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