People about Cosplay...
Costuming has been around a long time: we find artifacts from tens of thousands of years ago where they were used to portray a being or spirit. Often those who played the parts in costume were held in high regard.
A little time with kids or a parade group reminds us all how much fun people have – let alone when there is a formal play being staged. Costuming is fun; it’s fun for people to pretend, but it should be understood by all that it’s to be pretend. Problems come when the “role” gets mixed up with one’s being; the role defines the person instead of the person defining the role.
As Jack Nicholson famously said to Michael Keaton as they were suiting up for their roles in Batman (1989): “Time to let the costumes do the acting.”
When the role is more than the person, that causes psych problems.
Coming from a movie production background, you put on the parts of your costume that would interfere with makeup – possibly rubbing on your face when donning the apparel – before you put on makeup. None of the rest of your costume should be worn until it is just before “showtime”.
And costumers (both hobbyists and professionals) should be planning for makeup application and making a costume that can be put on without having to go over the head like a T-shirt does. Aside from the fact that this is easy to make, there really isn’t a good excuse for designing a costume that ruins makeup, or alternately, has to be worn while makeup is being applied.
I’m going to address this question from a different viewpoint. Why is cosplay popular amongst those that do it?
There is the factor of honoring the source material/fandom that you love. There is the creative outlet. Then there is the sharing of the work with other fans and making new connections with like-minded people. Getting complimented for your work can create a sense of accomplishment, as can having a photographer ask to take your picture. A three day event like a local comic-con or Anime/SF/Fantasy Convention can be more rewarding than a two week vacation in the tropics, to some people.
This all has a spillover effect, those that aren’t doing it, see the results and fun that those that are having and want to do it themselves next time. This keeps the world of Cosplayers growing at a currently staggering amount. I’m staff on a 2,200 person Anime Convention and we are constantly amazed at the ~60% cosplay attendance.