Subjects of Equestria! We are pleased to kick off the Nightmare Night Festivities and the 14th anniversary of the return of our beloved Princess Luna! Join us in celebration!
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Thanagor

Weirdly enough, I have worn a fedora before…though it was as a joke for my high school prom, and long before I was ever a brony. It was a part of the Zoot Suit I wore.
Da5ch
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) -
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.

If I ever go to my brony meetup again I seriously want to punch any brony who actually does wear a fedora. Stop fitting the stereotype perfectly! As a clopper I feel incredibly insecure when I see members of my own fandom look and act in ways that makes them look like brony stereotypes.
Background Pony #C77D
As someone who differentiates between fedoras and trilbys, Backy here is thinking of a trilby. Those are the really short brimmed hats you see neckbeards wearing, which were bought from places like Walmart. A proper fedora is often expensive (Mine cost almost a hundred USD for a CHEAP one) and has a brim of two to three inches.
Background Pony #E522
A normal T-shirt and jeans is what I wear every day of the week. Don’t typically wear a hat.
Background Pony #E05A
Wow ok I really screwed that up. I meant cops layer. Cows player cow player cows player GODDAMMIT AUTOCORRECT COSPLAYER