I have three antique hats (1950s era), a straw cowboy hat, and a couple baseball caps, but I rarely wear any of them. I'd say I probably get the most use out of the baseball caps because I like to wear them to the pool in the summer. I think you really have to have the right face shape or something, like you were talking about, to look great in a hat...and unfortunately, I don't have it.
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