Bruce Wayne
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I paid $750 for my Optimo black derby & oxblood diamond this past fall.
The lowest price that I have paid was $60 for a 4X Stetson Open Road, on Ebay. The highest priced hat was $670 for a fur felt fedora from Optimo in Chicago.
Hmm... I have a 60 or 7 1/2 head so the "steals" are few and far between.
For fedoras I got a good deal on a 1940s Dobbs 20 with the guild edge and wind trolley because it was dirty/dusty and the seller throught it was just a beater. I brushed it off and steamed it to reshape it and its a nice hat. Actually, it was a rare 7 5/8 and was a steal and I got it for a little less than $100.
Cheapest vintage was a Champ 1950s tapered one (with wind trolley!)I picked up for only $50 or so. Its not my favorite hat but works very well with 1950s suits:
Most expensive a rebuilt grey Borsalino at about $200 but its my nicest fedora so well worth it.
If we move away from Fedoras I got a couple of great deals on two vintage silk plush top hats (one American with original leather case the other French I picked up in a French flea shop for less than $50!) but getting them re-sized and refurbished is not cheap...
Good looking hats, and suits. I assume you are still a "working unit," and these are business attire?
Thanks, I have to ask what do you mean by "working unit"?