My normal choice for casual shoes was a leather blucher like the one above. When I was younger I wore them with socks but when I got a little older I lost the socks and rolled up my khakis to show off my skinny ankles. Sometimes instead of a blucher I would go with a deck (boat) shoe in a gray or brown (never blue) with white siped soles. These were mostly school shoes but could sometimes be worn to casual church events.
My church shoe was always a Norwegian (weejun) style "penny loafer." I considered these to be stiff and uncomfortable so the idea of wearing them by choice with jeans never occurred to me. Also, the leather sole was slick when new so getting any traction when running was impossible. Because of this, the first thing I would do on the initial wearing was drag the soles over as much concrete as possible in order to scuff up the bottoms. The "cordovan" or burgundy color was normally a safe choice because it would go with khaki, blue, or gray pants (which were the only three colors worn by boys at the time.)
My grandpa considered it his duty to make sure that I always had a pair of cowboy boots that fit as well. These are the shoes that carried me through my formative years. The Nike Cortez was reissued as a retro style some time ago. Versions of the blucher are available from L.L. Bean and Quoddy. The omnipresent Weejun (originally from Bass) is now available from J. Crew as well as other outlets.
What are your childhood shoe memories?