No one—save Beyoncé, Faye Dunaway, Judy Funnie and that beatnik poet in An Extremely Goofy Movie—has ever looked natural in a beret. Fascinators are just that: fascinating to look at, but unlikely to make you feel comfortable unless you’re attending an antiquated royal wedding. And let’s not get started on the fedora’s reputation. Sometimes, hats just make you feel silly. No other accessory makes you question your sense of self or prompt world-shattering introspection in the mirror: Are you wearing the hat, or is the hat wearing you?
Still, this challenge doesn’t discourage us from trying to find the perfect chapeau, but the combination of casual and interesting hat often eludes us. You can fall back on your basic dad hat or easy bucket, but we found 25 styles that strike the perfect balance ahead.