I've been hunting for just the right hat for a good while now, being in CA I feel my quest coming to an end... Dolls whatcha think about a gentleman in a hat =)
I definitely want something with a latin flair to it, short vs tall, and a thin brim. Not sure about the feather tho...and i'm leaning towards black since I seem to wear that more than shades of brown. If the second one came in black...it would be mine.
Head shape does indeed factor in. If you have a longer dome then some hats that have a deeper crease may be uncomfortable or it may change the crease when worn at the right level. Either that or it'll look like you're not really wearing it, and just set it atop your head. Face shape is a lot more important. Unfortunately the best way to really see what works with your face specifically is to go into a hatter. (of which there seems to be short supply in CA -I find myself in the central valley) Oval faces can usually wear pretty much whatever they want. Round faces would do well with a higher crowned hat. Heart shaped faces, like their ovular cousin, have a variety of options but as a general rule should go with a medium brim, just to keep their chin from looking too narrow.
But, hey, like any other piece of clothing, the best way to really see what works with YOU is to try it on. I'd suggest going to your mall and just walking around to see what you can find. While they may not be classically vintage, you'll probably find at least one you'll like, and in the meantime you can look towards shape and form and how it compliments your style.
Hope I helped, hit me up and let me know what one you went with. Personally I like the gray porkpie, but that's just because I generally prefer felt to straw.
My BF has the head for any hat.. hes so lucky.. a gatsby, boater, fedora, cowboy, flat cap, you name it!! he has one like the pics above in black leather.. a little less boater, a little more fedora.. but its HOT Im trying like hell to remember where he got it.. but I can't...sorry :(