I have some costume philosophies, for Halloween in particular, but also just in general. I don't generally like wearing a costume that you've seen before. IE apart from thinking that dressing like Steve Jobs is a bit tacky, I wouldn't do it because you'll see other Steve Jobses at the party. My costume should be something you won't see from anyone else.
Preferably, it would also be something people would recognize. If I dressed as Soren Kiekegaard that would be kind of cool, but no one would get it. I don't care if most people don't get it, but at least my target audience should get it. I don't have a lot of philosopher friends, so Soren is out.
I don't like spending a lot. I don't mind spending a bit, for instance my welder goggles for Dr. Horrible weren't inexpensive. But I don't think would makes the costume special is the cost. It's the thought of the costume, which may translate into cost or time, but it's nicer if it doesn't. My costume cost 3 dollars this year.
I don't intentionally do so, but the majority of my costumes come from pop culture. In the last few years I've been Zach Galifianakis, Robin Sparkles, Dr. Horrible and Jemaine Clement. All are from recent film and television, but that's nearly happenstance. Nearly, but given the amount of time I devote to following such things, it's not surprising that the costumes end up coming from there.
This year I was Ron Swanson. Chances are, you don't know who Ron Swanson is, and that's fine. That indicates you probably have more of a life than I do. But if you want to understand the various bits and wonder of my costume, you can watch the following clips: