"I've been thinking of getting a pork pie hat made, and VS Custom Hats and Optimo in Chicago are the names that keep coming up. Would you mind giving me an idea of how the process works?
Specifically, my problem is that I don't know a heck of a lot about hats other than the basic shapes, so I don't know what all the options are. How much guidance do the makers provide for a neophyte?"
They are both quality makers with excellent service. Optimo is $500 for a beaver felt with pre-war ribbon. Fawcett is $305 for the same materials and the quality is very close (Optimos may be sewn a bit better, but I haven't noticed a difference).
Optimo's shapes are as conservative as London's James Lock. Fawcett's shapes are a touch more flamboyant, but he reigns in if you are clear that you want conservative. Fawcett sends you a conformer for an exact fit where Optimo conducts a phone call with you and then makes your hat in a standard size. On the other hand, Optimo has a wider selection of straws. Their Milan is particularly nice.
You won't go wrong with either maker.
"I have a couple of questions about cool-weather fedoras:
1) How do I determine what style/shape/size brim and crown is best suited to my face? I have a longish face and a spacious forehead -- recommendations are welcome. My preference would be for a high-ish crown and very narrow brim, but this is based on little beyond personal taste.
2) What would be the most appropriate color if I was to buy a single hat for winter wear with several different dark suits? My instinct would be to lean towards mid-to-dark gray with a charcoal or black band.
3) When it comes right down to it, can a man in his mid-late 20s (in a rather poorly-dressed town like Washington DC) really pull off a fedora? (I know this sort of question is usually answered with something like "a man only looks good in clothes in which he's comfortable and confident" and all that, but... really?)."
I have found that no-one looks at our dress nearly as much as we think about it ourselves. By your second week with a fedora neither you nor passersby will notice.
If I had to choose one felt for the city it would be dark gray, unless I wore a charcoal overcoat every day. In that case I'd choose brown or navy.
From what you write, a normal brim width might help balance your face but any good hatmaker will help you to determine what will look best on you.