Ahh, the fedora. Be careful not to match it to your suit, or you?ve just joined the mob. Fedoras are the best hats for all seasons in my opinion. Time of day is the only factor I worry about. It?s the perfect spring and fall hat, and for snowless winter afternoons and late summer nights. Stick to the plan of never wearing a fedora before happy hour in the summer and after in the winter. That?s 5 o?clock for the non-drinkers. Maybe if the weather is nice, move that up to 4.