I thought I'd throw my hand in trying to copy the Homestuck style, drawn with a mouse on MS Paint (absolutely none of this was copied, I freehanded anything the circle or curved line tools didn't help with). I love how my hat turned out, I heavily referenced both my real hat, and John's Dad's hat and came up with this...

I should definitely make more poses, I mean, I could do a parody/tribute in the style if I have enough time