You can overdress in a way that still makes it super obvious you're not being "dressy". Unconventional accessories are always a good pick.
Like, you can be wearing the nicest of tuxedo pants with the nicest of button-down shirts, but adding just the right hat or scarf magically turns it into a casual outfit.
Agreed. As someone who wears a fedora regularly (actually a black Akubra Hampton), it gets a very different reaction depending on the context. I've been stopped on the street once by someone who said "Cool hat! So you're a Bronie right?" You don't want that.
But when I'm travelling overseas, it gets a much more positive and inquisitive reaction. Many times people have used the hat as an ice-breaker to start an interesting conversation with me. And if you're the only person with a hat in a group, it can be helpful branding so people recognize & remember you.
Interesting. My experience in the US has very much been the latter. What do you typically wear with it? I definitely think it says different things with slacks and a sport coat then jeans and a hoodie.
Like, you can be wearing the nicest of tuxedo pants with the nicest of button-down shirts, but adding just the right hat or scarf magically turns it into a casual outfit.