The word isn't actually used here very much, there never (SIGH) being much need for either. But overall, I'd say the first thing most people would think of would be the sled def.; that type of hat is generally referred to as a knit hat. That's the way they're often advertised in stores. Though the ones I put in my great-nephews' spy kits were called watch caps.

P.S.--the first thing I think of when I see DARE is Drug Abuse Resistance Education. Made me wonder!