Q: "The old man is wearing glasses, a scarf, and a hat." Does this mean that "The old man isn't wearing his hat and scarf today."?
A: no

Q: "A man with a beard and an orange cap smoking outside." Does this mean that "A man is smoking outside."?
A: yes

Q: "Boy wearing blue cookie monster shirt holding up a leaf from the fall." Does this mean that "the kid holds a leaf"?
A: yes

Q: "this man is sweeping the sidewalk." Does this mean that "A person doing something outside."?
A:
it is not possible to tell