Homestly, if you do want to wear socks, it would probably look fine, just make sure thay arent too dressy, as the topsiders are pretty casual. Perhaps argyle would look find, if thats you thing. I am a devoted boat shoe man, both for sailing and pretty much any other activity. I have a pair of the same ones you just bought, and I wear them with everything from nylon shorts while taking out the garbage, with shorts and a t-shirt, to kakais a buttonup and perhaps even a blazer for a dinner out. I would draw the line at never wearing wool pants with them, but any kind of caual material - cotton, linen, etc. looks great. Also, I pretty much consider them to be a warm weather shoe and try not to wear them once it gets cool outside.
Anyways, great purchase, and I'm sure you'll enjoy the shoes. Theyre so comfortable and versatile that they can be worn on many different occasions and still not look out of place. And I still recommend no socks...you'll probably find that its just more comfortable, not to mention the fact it looks better.