I'll post a picture below, but today on my vacation I wore a pair of black loafers with some light, almost white khaki shorts and a plain black t-shirt. A female companion laughed at me and said the loafers look stupid with the shorts as they are too dressy, but I thought they looked pretty sharp with the crisp khaki shorts, almost like a slightly more grown-up way of wearing Sperry Topsiders. Sitting here insanely self conscious about it because I had no idea it was perceived any other way. Please let me know who is right. The shoes are the Prescotts by Bostonian.