[KyleGoetz]

Originally Posted by Sashimister

First and foremost, Japanese speakers don't use pronouns like you do. 彼 is a big no-no.

We don't use 着る when we want to know what shoes someone is wearing and whether or not s/he is also wearing a hat as well as what clothes s/he is wearing. In fact, we don't even use that 彼は何を____いますか format because it's impossible for all the verbs that you mentioned.

Native speakers would say 「（その人は）どんな格好（かっこう）をしていますか 。」.

If you say 何を着ていますか, the reply will only include the person's top and bottom.

Thanks for the tip, SM