I wear hats on the bike and in the winter. I have a standard cycle cap for summer riding and a very old style hat (can't say I know what the style is called) for winter riding. Also a wooly hat for outdoors in winter. Otherwise no - I don't wear a hat.
I bought a Russian fur hat (copy) in Prague a few years ago. Since then I bought a Leather Aussie cowboy hat and a straw trilby type (in Italy 2 years ago for the sun). Plus I always have a helmet on the bike.
My Grandad always had a flat cap for everyday wear and a trilby for best. He had several flat caps. Some for gardening, some for going to the shops and his newest one if we went out as a family and he wanted to look smart. As they aged they got demoted eventually to the gardening cap then the bin (or his shed more likely).
I have lots of hats! I like hats. They range from a very broad brimmed straw hat, through various summer hats (I can't stand to have the sun on my head, I get a really bad headache), to various ladies' dress caps, fleece hats for hillwalking, and woolly and (synthetic) fur hats for winter.
I have some fleece hats, a much treasured 'Kelloggs school of Executive Management' baseball cap...
BUT
Without a doubt, the best and most versatile hat I have is a green Tilley T3. Great in the summer, great when it's pissing down. £50 seems a lot but I'm a total convert. Worth every penny.
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