147 voters

25 Celebrities Wearing Questionable Hats

1.8k votes 147 voters 5.6k views25 items

The celebrities on this list have all shown poor taste in hats, and we want to break the news about their ugly hats to them gently. Like most human beings living on Earth (note: we are not astronauts), we take our fashion cues from the rich and famous. Popular thinking leads us to think that celebs are the best dressers because they make enough money to pay someone to tell them what to wear, or they exist in a vacuum where no one tells them that they’ve made a terrible fashion choice. As everyone knows, the easiest type of fashion to mess up goes on your head. Even a simple snap back can turn you from a respectable member of society into a frat bro in a matter of moments.

If you’re a celebrity and you’re wondering what kind of hat you should wear today, go to your hat closet and find all of your bucket hats. Now throw them away. No one has ever looked good in a bucket hat, and sorry, you’re not going to be the first. The same goes for anything oversized and fuzzy. You’re all really cool and we believe in you, but fuzziness just isn't going to work. We know these ugly hats are only minor setbacks and that you’ll get past them soon enough. But until then, remove all your headgear and trust our judgment rather than your own.

As for the rest of us non-celebrities, we can explore this roundup of 25 celebrities making questionable hat choices. Vote up the celebrities wearing the most questionable hats, and if you think we’re mistaken about some of the fashion on this list then defend your favorite celebrity and their ugly hat in the comments.
  • 1

    Who Bought Biebs a Gift Card to the Stupid Hat Store?

    Photo: flickr / CC0
    Agree or disagree?
  • 2

    What We Talk about When We Talk about Lost Boys

    Photo: Wikimedia Commons / CC-BY
    Agree or disagree?
  • 3

    Sarah Jessica Parker and the Hat from Another Dimension

    Photo: Wikimedia Commons / CC-BY
    Agree or disagree?
  • 4

    Nicki Minaj in Rarely-Seen Waluigi Cosplay

    Photo: Metaweb / CC-BY
    Agree or disagree?