Wear some slim khakis and parade in your penny loafers with your feet in the nude.
Feels good, man. I also do so with boat shoes, and not only when i'm boating.
I agree about that as you are probably thinking about when loafers are way too dressy to be worn with shorts let alone sockless or when the socks are too high. That's what makes the elder unfinished look., but I was talking about t-shirts (modern), shorts, and casual loafers (leather brown or suede or other colors) not black loafers, varnished or with tassels or masks, but loafers for every occasion or boat shoes (if with laces) that can be dressy but also an everyday shoe. And definitely never wear dress socks but short ankle socks, just like those i would wear with converse or other closed shoes. Sockless migh look better with these shoes but if you like them you can go creative with shorts and ankle socks of many color, in my opinion, just avoid too bright colors and white, black is always a safe choice.
An exapmple might be these shoes http://images.askmen.com/fashion/articlepics/tip7.jpg