I have a picture book of 1800s clothes and hats. Because of the expense of film, most of them are of British upper classes. In it some of the pictures really and truly bring out and empathize the Simple Simon effect. And also unfortunately, that's the kind of look I see peering back at me in the mirror when I try on a hat.
The only one I look barely nice in is a 1920s one copied from a picture of my Mom's aunt. Auntie had enough smarts to not wear it in more than one picture, and I took her unspoken advice. Although I do keep on trying, I love hats and hope to one day find one that makes me look nicer than I do.