People about Cosplay...

Putting aside for the moment that the tone of the question doesn’t imply the most open of minds, cosplay is – simply – acting. Do you consider Mel Gibson, Ken Branagh, David Tennant, Cumberbatch, et. al. immature for wanting to dress up and act as Hamlet? Cosplay is a similar – if not identical – mindset: people, inspired by characters, possessing the right combination of talent, bravery and self-awareness, performing as said character for an audience. Whether it’s a convention stage or a Broadway stage makes no difference. The person who portrays Deadpool or Master Chief is very much spiritual kin to the person who plays King Lear or Hamlet. It’s wrong to praise one and denigrate the other based on the source of their inspiration, for to declare which works are “great” and which are not is subjective or worse. Still, even if most consider it blasphemy to compare Marvel to Shakespeare, the motivation to portray characters from either realm is identical and the healthy mindset WON’T criticize this, realizing that whatever it doesn’t “get” is not automatically inferior or invalid.

PS: Ironically you will find, if you but ask, that most cosplayers as children were very successful Trick or Treaters, as Halloween is quite often the “bug” that bites them for their subsequent motivation.

It really depends on:

1. The costume. How is it made? How is it put on? How hard/easy is it to wear?
2. The cosplay. What cosplay? What makeup does it require?
3. Individual preference. What works best for you?

There is no 100% rule for this. If it requires body paint, doing that before putting on the costume may be best. If the costume requires going over the head, putting makeup on after the costume is at least halfway on may be better. Same with wigs and other accessories.

I tend to decide on and create my cosplays with makeup/wigs as the last things to put on, not the first. Because for me that is easier. And since I am allergic to body paint, that isn’t a concern. It varies from cosplayer to cosplayer and cosplay to cosplay.

I would recommend starting out with something simple.

At my very first anime convention, I only had about a month to prepare and didn’t watch a lot of anime. I did Android 18 from Dragon Ball Z as I had most of her outfit already and had the right hairstyle for it. I only had to do a bit of alteration and get some extra items from eBay.

Each time I have cosplayed since then, I have expanded my range. I discovered I have a knack for props and makeup but am not very good at sewing. Therefore most of my best cosplays have involved some sort of prop or latex bloodwork. I am still practicing my sewing so I can incorporate that as well.

Play to your strengths and you’ll soon discover which areas you prefer to work in.