I just started putting Tom into Hatsune Miku cosplay and laughing like crazy. That's as far as I got before the humor just overwhelmed my being and I could not do anything more. I love the intentionally "bad" art style too. Great job!
P.S. If you're interested and want to see some seriously great dress-up games/character creators, let me know and I can recommend you some websites for "girl games" that are really really high quality.