Honestly, the trick to working a hat into your day-to-day rotation is that there’s no real trick at all. Just wear one — preferably one that’s made from fur or wool felt, and doesn’t come from a mall. There will be trial and error. Sometimes, you’ll feel like an idiot. Other times, you’ll feel like you’re crushing it. And when the latter starts happening more often than the former, you’ll know you’re doing something right.