Q: "A man wearing a uniform and hat at an amusement park with people around." Does this mean that "The man is in a hat."?
A: yes

Q: "Two people wearing dark hoods, one in a black shirt, one in a green shirt, are surrounded by branches." Does this mean that "Two people wearing are dark hoods and one has a light black shirt"?
A: it is not possible to tell

Q: "A brown dog in snow is biting at a piece of pink cloth." Does this mean that "a brown animal is eating something pink"?
A: it is not possible to tell

Q: "An older man in shorts, showing healthy-looking legs, astride a bicycle, pauses at an intersection" Does this mean that "An older male is at the intersection."?
A:
yes