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For Cavanagh hats, one of the best clues to narrow them to certain time periods, such as decades, is by the crest design used in their liner tips.
Most important is the address for the Cavanagh shop, displayed below the shield.
The earliest versions on Cavanagh hats say John Cavanagh, Ltd, and "247 Park Avenue, New York." This address in the liner dates from the opening of the store in November/December 1928, though Cavanagh didn't apply for a trademark until December 12, 1929. These versions are from 1928 to 1936, and probably on the earlier side.
The first clue is this use of a rather rare debossment, "Cavanagh Make," as seen below.The second label below featuring a lot number is from the circa-1930 Derby, though this lot number appears to have far more in common with a "To Duplicate" or "Reorder" number. Photos from left to right, or top to bottom: "Cavanagh Make" debossment on the Derby, an Opera hat, the inside of the Derby, and a label from a circa-1930 Derby for comparison.Because I knew that John Cavanagh liked to drop in from time to time on the Cavanagh division's curling bench to curl the brims on some of his branded hats, I had originally hoped that his initials meant he had personally curled the brim on this particular Derby.These have only shown up on about three hats I have seen so far, and no trademark was ever filed for it.I believe it to be from the first year or so of Cavanagh production, and then its use was discontinued. It has the Cavanagh Make stamp, and inside the sweatband are the handwritten initials JJC, and a plain factory label, neither C&K nor Cavanagh.