Q: "A baby with a dirty face." Does this mean that "The baby is messy"?
A: it is not possible to tell

Q: "A boy with a black beanie hat and glasses strums an acoustic guitar." Does this mean that "A kid plays the guitar."?
A: yes

Q: "The little footballer takes the field." Does this mean that "The footballer is wearing a shirt."?
A: it is not possible to tell

Q: "A man with a shirt on his head, wearing a plaid shirt, leaning against a painted blue wall." Does this mean that "there is a guy leaning against a wall"?
A:
yes