When it comes to headword, it'd be neato if there two tiers to it. You have the primary headword, like a mask, and if its' compatible, you can place a second-tier headworn on as well. For example, a bear mask + stovepipe hat. Obviously not all headworn would "stack" well, so there'd have to be some restrictions.
A similar idea would be to add hats to some of the mounted trophy animals or hats/underwear to antler horns. A full size bear, wolf etc etc with a ale mug in hand.