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Idk if this is supposed to work like this but when I bought the clothes for Annie then the ability worked even when she wasn't wearing them

That is how it is meant to work. You can stack all bonuses for stage. And after you bought her clothes (now I'm not sure if just once or couple times) you can change them for free. BUT to have active effect you need to pay for it every time unless you restarted or left stage without completing it.