I will say this again.. if I ever saw anyone walking around with a Keepall as their daily bag and only had 2-3 items in it.. I would call the tacky card right away. I wouldn't care if they were a male or female... Walking around with luggage isn't cute unless you actually have clothes in it or something.
I saw some Italian guy come into a restaurant with one. It has a really good patina and was well used and it actually looked really good... but he could have had any reason for carrying it. Maybe it wasn't his 'daily' bag.