Note: A hat like that today from Optimo Hat Co. (Chicago) starts @ $595
This thread is wonderful! I hope to make some good contributions from my meagre collection. I wonder if one reason why so many young folk do look affected is because they use the hat to make up for deficiencies elsewhere in the outfit, missing all the other details. TTO has just shown how it's done properly, by a guy who's not been around during the heydey of hat-wearing. I myself will admit that any hesitation I have to post fits wearing hats is due to my lack of confidence in the fit of the garments rather than the look or fit of the hat. To that end, here's a pic of a recent vintage store purchase of a deadstock Adam's summer hat. A little large for my small face and frame, but very functional as I walk about campus and around town a bit.
omgitswes: it kinda depends on where you are. Upscale department stores usually have one or two 'proper' hats. Lower end ones usually only have paper/cloth fashion crap. Dedicated hat shops are the best option; they're usually only present in decent-sized cities these days, though. What's your nearest city?
edit: panama can look fine with a casual outfit, though it depends how casual you're talking. As a rule of thumb, if your shirt has buttons on it - even including polos, at least *nice* polos - you can probably pull off a panama with it. (I wear mine for golfing, with just a pair of golf pants and a golf shirt, all the time). If we're talking 'beach shorts and tank top' casual, it might look a tad incongruous. I have a more rustic-y straw hat I pull out for super-casual outfits - it's a very wide weave made of very rough straw, with no real hatband but a stripe of the straw dyed black in imitation of one.