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No. You can't enchant helms or headgear, and aside from the headband of intellect, I don't think there is any headgear you can create via crafting - maybe a circlet of blasting, but that's just a guess.
I thought my female pally looked kind of rockin' in the swashbuckler's hat - until she found a major circlet of blasting. Now she looks like a princess - in plate mail! The Regal was also fairly good. I'm still after the Helm of Briliance but right now it's TOO expensive.
For Rogues, the Watchman's Helm was pretty good. One of the merchants in port llast has a pickpocketable helm called the Rogue's Hood which is good since it gives you immunity to knockdown and poison.
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“Every tavern’s an opportunity, I say.”
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