Most Helpful Girl
It depends. Did he invite you to a movie? Or, are you going to your favorite restaurant and he isn't sure about the atmosphere? Is he doing something new to him, but something you like to do?
For instance, if you are going hiking and he doesn't usually go hiking (but you love to go so he is doing it for you), then it is not weird to ask what he should wear. Plenty of people do it.
It might be weird if he invited you to go see his favorite band in concert. He should be telling you what might be best to wear. :-)
Maybe he is nervous (so what).
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