Hi, I'm interested in working on your browser dress up game project. If I understand correctly, all graphics will be provided (characters, backgrounds and clothes) and the goal of this game is to teach kids how to choose appropriate clothing for different occasions. If that's correct, I can complete this project in 3 days. Your satisfaction is my priority, so I will keep working on this until you are happy with the result.
I would make the game exactly how you described it, but I have a few ideas for improvements. It would be a browser game that requires players to drag and drop clothes onto their characters. The process has to be repeated for each background. Items that have been used, can not be selected again and in the end, the game shows all of the selected items for each background.
How will the kids know if they selected the right clothes? Will there be a teacher to tell them or maybe it would be better if the game told them in the end? Maybe it could give them score? Then they could try to play again to improve their score, which might help them learn faster. You wanted there to be two characters at once, but I think it might be better to allow player to select just one character in the beginning. Boys would choose a boy and girls would choose a girl.
Feel free to contact me to discuss those ideas. I look forward to hearing from you.