As long as I have a lid on and a cigar I'm fine; combo not important. Of course, being a Floridian of Cuban descent, I typically wear a panama, a guayabera shirt, and a stogie. Cigars I enjoy frequently are: Cuba Aliados Regordo and Puros Indios Gordo Double Maduro (my everday cigar), Ashton...
I have three Feds: carbon gray, tawny fawn, and mid brown. They have all been true to size. And in comparison to the new Stetson's I own, they out perform them in every way. Good hat, especially, for the price.
The only factor that determines what hat I wear is my clothing. This includes panamas in summer time. Aside from that my head is always covered, rain or shine.
I agree with Spatterdash and RBH avoid the new Stetsons. I own several of them including the temple, which I always wanted--what a waste. Go with the Akubra Federation. It's cheaper, better quality, and better looking. It seems like anything is better than a new stetson.
I own two Borsas (light gray, navy blue) and one roll up 214 (brown). The roll up is softer felt, the other two are stiffer, but I like them for new hats. They are definitely better than the Stetsons I own. I don't wear them that often, so I cannot comment on their durability.
I, too, know...
When I was with the PD I got Dick Tracy from the guys all the time. I wore the suit, fedora, and had a cigar clamped between teeth. Seldom, I heard Inspector Gadget and once, I was asked if I was a mennonite. But what I always got, aside from gawking eyes, was the question "What's with the...
What's the bid deal if you do have hat hair? It's understandable and if people don't like it, well, tough.
And regarding applying makeup in cars, God only knows how many traffic crashes I handled because of it.
Keep your hair short and if possible avoid low crown hats. I have a modern...
I've learned to use my knee as a hat peg in crowded restaurants, if not an empty chair. I definitely wouldn't trust anyone with my hat. I do try to follow the basic rules of hat etiquette as I believe an adherence to such rules promulgates high self-esteem, morality, and respect. At least...
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