It depends on its rarity. I'm actually looking for a leather Earnhardt hat as I have had 2 in the past and love their longevity. I am and always will be a die-hard Earnhardt (Sr.) fan and will always wear nothing but an Earnhardt hat forever. Monetarily I'd think anywhere between $35-$65. That would be new condition.
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Less than you paid for it. The expensive Ironhead collectibles were made in the 2000 season, and before.