Sootyowl: I don't know if you pass, probably would be able to tell if the pictures were larger/clearer, but a blind look had me wondering which way you were trying to cross. Whatever that says.
Kawaii Pocky: Passing is going to be tough for you because you have large eyes, a small mouth, and a round face. Perfect anime girl proportions, not an easy fit for dudes.
Are you wearing black eyeliner? I have a terrible eye for makeup, but if you are, I'd suggest switching to brown when crossplaying. I've heard it works a lot better than black, though I've never tried it myself. I'd also suggest not going quite so heavy on the lip makeup, if you need it at all. You lucked out there, I think.
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COSPLAYS IN PROGRESS
Canterbury (Kuroshitsuji) - 30% - Kuro Gathering
Utatane Piko - default (Vocaloid) - 15% - Ohayocon
Boris (Alice in the Country of Hearts) - 3%
Jean (Shingeki no Kyojin) - 0%