Yeeaaah, I SUCK at planning for the weather. Like, I think "it's Oregon - we're gonna be rainy and cold forever"... then September comes and I'm dressed as Irvine Kinneas with his long coat, jeans, chaps (practically a 2nd pant), boots, gloves, wig, AND hat. Whoo. I can't even WEAR that one all day it gets so hot.
So, I've learned to CONSIDER the weather... but a lot of characters I wanna cosplay wear tons of clothing and k-con is the only con I can afford at the moment. x.x;
So, my list generally goes -
1) Have I made any prior commitments? (Groups, photoshoots, etc)
2) Do I like the character enough to cosplay him? (Him, yes, I don't plan on crossplaying, heh)
3) Will I wear that (whatever the outfit is)?
4) Is there a prop? I loooove making props. I enjoy it much more than sewing.
And finally, the general dead end of my cosplay dreams: Do I have the money for it?
Sadly, that last one has killed many. v_v