Not exactly. We are talking two different pieces of clothing. Σκούφος is (as Troll1995 said) a winter cap, for the head, while κασκόλ is a scarf. :P (But yes, someone could exclude the word σκούφος for the gender alone.)
I was given this question as a drop-down box, with the sentence "το μικρό ------ μου" as the only clue. Am I right in thinking that gender is the only way to determine the correct word, in this type of question? Are there other clues to look for?