Holiday gifts for your boss are the grown up equivalent of an apple for the teacher: they’re mainly a token of appreciation (ha!), so don’t worry about spending a lot. If you like your boss/job, you want the gift to be memorable, but not too personal; useful (so they are forced to think of you whenever they pick the thing up) but not presumptuous about their interests (you aren’t friends.) And lastly, they should convey respect and admiration. You know, bullshit.