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If you don't have one already, it would be a good idea to get yourself a hat jack/stretcher just in case you need to give your hats a little "nudge" to make them fit a bit more comfortably after they're broken in.Thanks, Snowman and Zombie_61.
It's better today. Apparently I'm a narrower oval than I thought. The hat is pressing above my eyebrows, like a tension headache. When I press in on the sides, I can tell it'll be fine with a little more wear.