if you don't know what I mean by bucket hat, it's like the one ice cube is wearing in this pic (on right)
Most Helpful Girl
I think they were cool when I was in middle school - which would be about a decade ago, give or take a few years. I haven't seen anyone wear one in years, outside of those who are actively hiking up mountains. I wouldn't go so far as to say they're stupid-looking, but I definitely wouldn't call them fresh - if anything, I think they're out of style for casual wear.