The shoes the OP posted are hideous, so no I would not wear them with socks, or anything else for that matter. However, the purpose of wearing loafers without socks is to be very casual. Basically like wearing sandles or huaraches, but with a little more protection. A dress loafer should not be worn without socks, but casual loafers, boat shoes, and the like, can be worn without socks if paired with casual pants or shorts. When wearing casual loafers with shorts the idea is that it is warm enough to expose your legs, and thererfore warm enough to expose your ankles. Anyone that wears shoes without socks in the cold is simply making the wrong statement ("look at me I'm an idiot"). Bare skin against leather can sometimes be uncomfortable or produce odor for some people. In those cases a shoe sock liner can be used (Johnston & Murphy, as well as others, carries various colors [black, white, tan] for about $8 a pair).