The hat is probably the most commitment-intensive accessory in men’s style because unlike most things you can adjust or reconsider it’s just sitting there on your head in full view of everyone. Which means the stakes feel higher and most guys either avoid them entirely or go too hard and end up looking like they’re wearing a costume. We’ve made both mistakes. The key things we’ve figured out are that the brim width should roughly correspond to your face shape and that the most wearable hats for everyday life are almost always the least dramatic ones. A simple wool fedora in charcoal works for more situations than you’d expect. A bucket hat in a neutral works for casual dressing without looking like you’re performing a specific era of menswear at people. A cap needs to be clean and fairly minimal to do the job properly. Start simpler than you think you need to and build from there.