Thanks guys!
The more I think about it, the more I think that it's a case that most all men secretly think fedoras are really cool and would love to wear one. But because baseball caps are the currently accepted fashion, and fedoras are considered accessories of a bygone era, to wear one would be either non-conforming to today's society, or somehow "weird". The fedora is one of the most stylish and masculine pieces of apparel a man can wear and much more practical than things such as ties. But there's this gut reaction from most people to associate wearing one with playing "dress up" or costuming a movie character (Indy, Bogie, etc.)
It's silly really. And just like y'all said, after the "Hey Indy" comment, a genuine compliment seems to always follow. I think a lot has to do with the wearer's reaction to the comment. If you look embarrassed, offended, or defensive about it, their instinct will be to snicker or think "yep, the guy's playing dress up as Indiana Jones". If the wearer's reaction is open, honest, and unapologetic, their reaction is more of "cool, this guy's got individual style and isn't afraid to wear what he likes, wish I could do that".
What's even funnier, is that in the year since I started wearing my "stingy brim" fedora (never heard that term before) to work, two other guys have started to wear dress hats in to work. One's a Indy adventurer style from Cabella's, the other's similar to mine, but black leather with the brim flipped up all the way around (reminds me of the one Sly wore in Rocky). I guess some lead, other's will follow.
What's also funny is that here in Houston, we have a Livestock and Rodeo show every spring that's HUGE. It's over a week long and people come from all over the world to attend. There's live music concerts each night and typical rodeo events. I always crack up at all the "cowboys" that come out of the woodwork during the rodeo week. Suddenly every banker, stock broker, carpenter, accountant, and Starbucks barrista is wearing western wear. From boots, tight Wrangler jeans, huge hats and belt buckles, even leather chaps and spurs. Most of these people have never even sat on a horse, yet they have nearly a thousand dollars spent in "costumes". And NO ONE has snide "Hey there Hopalong, where's the posse Marshall Dillon?" comments! It's like Halloween at the OK Corral.
But wear a fedora and a brown leather jacket......
sigh, gotta laugh sometimes.
JRabbit