Q: "A woman in a black skirt and dark red sweater with holes in the sleeves sitting on a trunk to put on red flame tights." Does this mean that "The woman is wearing a red sweater."?
A: yes

Q: "A guy walking down the sidewalk." Does this mean that "There is a man on the sidewalk."?
A: yes

Q: "Man boogie boarding on wave." Does this mean that "A man is sitting in the sand."?
A: no

Q: "Two boys are onlooking during an outside classical music performance." Does this mean that "Two boys are watching their favorite orchestra at an outdoor concert."?
A:
it is not possible to tell