If Jasper is going for a long walk and it's not raining, then he can be 'naked' haha. But when it's chilly I put on a hoody, but for cooler days in the summer, if I notice him shivering, I will put on a tighter fitting tshirt, to keep in body heat.
Jasper has alot of cute vests with funny saying on them and they are loose, and not really warm at all on him, so I keep that on him, if I want him to look uber cute