Hats are hard for me -- I have an almost comically small head. I started getting into them for entirely practical purposes (a first!): avoiding the sun on my face. Straw hats made me look like a peasant, cowboy hats made me look like a costumed cowgirl, nothing really worked. Enter, the bolero.
The bolero is a trending silhouette that also happens to be really flattering on a lot of face and head shapes. It transitions relatively easily from a summer outfit to a winter one, and makes you feel vaguely like a Spanish explorer without crossing the line into costume.