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I once glitched all the headwear in my inventory (which is quite large as my inventory included everything I'd stored in my locked box in Tenpenny Tower). I had mostly just junk things though, hats, bandanas, stuff that just didn't offer much damage resistance. You can essential equip any hat though. (Also you can easily get your unarmed skill up with this glitch by consecutively equipping two hockey masks. Each time you do this you will gain a temporary +5 boost to your unarmed skill up to 100.)

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