John Lofgren Monkey Boots Shinki Horsebuttt - $1,136 The classic monkey boot silhouette in an incredibly rich Shinki russet horse leather.
Grant Stone Diesel Boot Dark Olive Chromexcel - $395 Goodyear welted, Horween Chromexcel, classic good looks.
Schott 568 Vandals Jacket - $1,250 The classic Perfecto motorcycle jacket, in a very special limited-edition Schott double rider style. Vintage Dunlap duplex hat. Era unknown - perhaps WWII or earlier.
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Yes Scott... it is the one you sold. More photos and details posted in this thread.
On dating, I seem to remember you thinking the hat as earlier than I believe it is. My guess is somewhere in the range from 1938 and 1945, based on the Sizor patent and on the manufacturing tag, which appears to be a 1940s HCA variant.