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You have to get used to the beret idea.They come in several diameters,colors,weights,etc.
I found that a beret is as easy to wear in rain,wind,etc as a flat cap,maybe easier.When you arrive somewhere,a beret can be folded and stuffed in your coat pocket.Sure,you get some odd looks and comments but I find that kind of fun.
I don't mind getting odd looks. Once you accept you're going to be known as "the fedora guy," it's easy to move into other hat styles without much worry.
I'll look forward to seeing the photos.