@TweedyProf I have the shoes in the first picture (Carmina, dark cognac shell, Forest last). I would wear them with jeans in a pinch, but never do because there are much better choices. That is actually my favorite shoe as I find myself wearing them all the time, particularly when wearing an odd jacket and wool slacks (tie or no tie).
I'd like the shoe in the second picture with jeans more if it was a boot, but the scotch grain helps make it more casual.
When I'm in jeans, it's typically on the weekend, so usually chukka boots or shell loafers. Occasionally, a pair of color #8 sheIl longwings that are significantly more clunky in appearance (less sleek) than the Carminas if I'm wearing a sport coat with jeans. I'm looking to add a dark brown scotch grain wingtip boot in the Fall to wear with jeans as well. I've also got a pair of snuff suede balmorals on the Forest last coming soon and will need to see how they look to determine if I will wear them with jeans.
If I were in jeans more, my wish list would include: dark brown or snuff suede chukka's; shell boots in color #8 or dark brown; and suede loafers.