I am not a hat person. When I wear a hat any longer than about five seconds, I get something I call "hat head," which for me is the worst kind of bad-hair day. Consequently, I am willing to wear a hat only if I know that I won't have to remove it in public and if there's a guarantee that I'll be able to take a shower immediately once I do (privately) remove the hat.
I will wear a hat only if it solves a problem that is worse than "hat head." I have encountered only a few hats like that in my life. This is one of them:
The sou'wester hat has its origins in Cape Ann, Massachusetts, but it's also wildly popular in Nova Scotia. I bought mine in Halifax as a souvenir thinking it would be amusing to make my husband wear it when it was his turn to walk the dog in the rain. It seemed best suited to someone who had a beard that smelled like raw cod, like this fellow here:
Then one day it was my turn to walk the dog in the rain. Not just any rain, either--more like an epic hundred-year-flood kind of monsoon. The kind of weather that makes you not care what you look like. So I put on the hat and headed out, hoping not to encounter anyone I knew. Happily, I didn't, as everyone I knew probably had the good sense to stay indoors. I may not have looked fashionable, but I discovered that what I thought was a goofy souvenir was in fact one of the most useful things I have ever bought on vacation, kind of like a cozy umbrella for your head. The flannel lining kept my head warm, the flaps protected my ears, the rolled brim in the front worked like a gutter, and all the rainwater ran off the sloping backside.
That was over twenty years ago. I still have my sou'wester, and I rely on it for doing outdoor chores in rain and sleet and any other kind of wettish precipitation. These Canadian-made hats are available from the Dock Shoppe, of Toronto, and from the Bluenose II online store, run by the Lunenber Marine Museum Society, of Nova Scotia.