Can I enter?

So here is the thing, I want to enter the masquerade at a con in July. I entered this same costume in May at a workmanship contest (not a masquerade) and won best novice. I am building on to the costume for July so it will be different. Can I enter this costume in July as journeyman? I am also worried that one of the same judges is judging the con in July as well, so she has seen this costume before. (But I am drastically adding onto it)

It really depends from contest to contest, but generally speaking, once you win an award with a costume, it either is against the rules or bad form/in bad taste to enter the same costume a second time at ANY competition. My best suggestion is to contact the organizers in charge of the contest and ask them.

Check the rules of your contest, but from what you said, it is probably okay? I have never known anybody to care if you are going up a category, especially if you are adding things. The question I have is the relative size of the conventions. If the May one is smaller, you are almost definitely fine. If the May one is bigger....maybe? You're still going up a category, so probably okay, unless your July con is drastically smaller. Do check the rules though, some contests only want new costumes.

Yeah, you'll have to ask that particular contest, not us.

GENERALLY...entering up a skill level and making changes to the costume? Totally kosher. At SOME conventions. At others? Not at all okay. At still others? You might even still be able to re-enter at novice. It really, really, really depends on the director in charge and the rules they've laid down. If the rules on the convention website aren't clear, email them directly to ask.