This is a question that, depending on the person and reason for being asked, can go many ways.
For example, when V and I went to Jackson, I asked her what she was wearing/packing so I could pack accordingly.
While on a conference call at work we were discussing face-to-face contact for the next meeting. One of the callers stated they wanted to physically get together so they could see me, my hair, my clothes, my style, and then asked what I was wearing. I’m not falling for that question on a conference call. Not again anyway.
Last example: I received a text with the question, “What are you wearing?” I replied, “Same thing as earlier, minus the jacket. Oh, and minus the wool panties, they were just too itchy.”