I have found that the "strap back" hats like those fit large heads better than some of the other varieties. I stay away from anything that's a velcro-back, they always have way too small a radius for me. Fitted is always best as you say, of course. I'm glad to know that I am not the only hat lover with a plus-sized melon. I can't really wear anything but a fully structured, fitted hat. Some of those slouch fit jobs will fit around my head, but almost none of them are deep enough. Ponder on that one for a minute. I would HYPOTHETICALLY go for the roster shirt IF such a shirt were to become relevant. same here, pretty much only fully sized exact fitted hats work for me, this M L XL fitted stuff is often too small as well (wearing XL). I wear New Era Fitted size 7 3/4