I don't have that many hats to choose from...BUT, it would have to be my Fawcett Black Cherry. I think the color goes with everything and would even look good in a fire.
I replied to this almost a year ago. While I still love my ORs, including a very nice tall-crowned one I have in fedora style, my new favorite grab-it-and-go hat is my dark brown Royal Stetson Whippet clone:
With a 2.5" brim, it reminds me of the hat worn by Gary Cooper in "For Whom the Bell Tolls." A 6 7/8, oddly enough it fits me like a 7.
It also helps that I keep it on the bookcase by the front door. It'd be right to hand anyway.
Given the parameters of the question, I have a vintage Borsalino that would be difficult to replace, so I'd grab that. Everything else I have is easy to replace.
Assuming I'm grabbing hats at all. I'd more likely be grabbing trumpets.
My hat with the most remarkable felt is a Churchill Beaver Fifty, but I'd save the hat I wear most often: a simple, old Burton Taylor clone of an early, unlined Stratoliner.
This is a ROUGH question. My best two hats are from Tony B and Mike Moore. They're both better because I knew what crown and brim fit, and what style I really wanted. Unfortunately, they're also the two that match my usual clothing choices. I already HAD a black hat and a brown hat when I bought these two.
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