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The liner tip is the top of the liner inside the hat. The tip logo is the crest on that piece of fabric. I agree with Moon, 50s - maybe early 50s as there doesn't appear to be a plastic cover on the liner tip (these were introduced in the 50s as a response to the goo guys started putting in their hair).
The PRofessor's page helps, as well. http://www.thehattedprofessor.com/datedobbspart2.html
The PRofessor's page helps, as well. http://www.thehattedprofessor.com/datedobbspart2.html