Hi Miles,
I have a half bald wig, hobo style which works very well for me, you could try having your wig trimmed.
My make up is Ben Nye cream white, red grease pencil, black grease pencil, light aguaste and a gray grease paint with a stipple sponge for my beard. I have a natural beard and moustache and use the gray to darken it.
For the gloves, take a pair of white gloves, put them on and mark just past the finger kunckle. Take them off and cut them at the mark you made, turn them inside out fold the fabric back and stitch them all around. When you turn them right side out you will have fingerless gloves that hold up well not only when you wear them but also when you wash them.
I know that some of the other Hobo's can give you more ideas.
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