I may be going against the frat bible here, but I am not a fan of the hardcore going barefoot in boat shoes when it's snowing outside rule. Some firmly disagree and I have no ill feeling toward them, but to me it is just as dumb as when guys wear their Croakies and Del Mars at night (can't you just leave them hanging off your dashboard mirror after hours?) or wearing shorts so short that their boxers creep out when they sit. I am all for being preppy, but these examples that push the boundaries to the extreme just for the sake of staying true to the preppy lifestyle are kind of ridiculous, and as a trad man at heart, I'd much rather fulfill these codes of valor in a utilitarian, common sense kind of way and to avoid the WTF? stares (for the wrong reasons anyway).
Old Navy multi striped socks
So boat shoes and socks. Are they polar opposites? Boat shoes are inherently a warm weather shoe and I rotate them with my L.L. Bean Blucher Mocs in the colder months, but when I do wear my Sperrys I always pair them with socks. If it is of season or it is less than brisk degrees (below 60 in my book) outside then you should adorn socks, unless you live in a tropical climate and therefore free of a lot of worries we northern people deal with.
But because boat shoes are a casual shoe I tend to pair them with atypical or 'fun' socks. Argyle, wool or hiking, and fair isle socks can be both under-stated and appropriate for daily seasonal wear while GTH patterns like multi-striped, rugby, and bright colored socks for preppier occasions.
Depending on how dandy you want to appear, socks can be used to add personality to your wardrobe and can make as loud as a statement as going sockless in below-freezing temperature. I normally reserve my 'louder' socks for casual events or when I am feeling ironic. Below are examples of boat shoes and socks, however you can adapt this to any other shoe you wear regardless of season. Just be mindful of what you wear your GTH socks stuff to....class is ok to illicit those WTF? stares (for the right reasons), but probably not at funerals.
J. Crew yellow socks
J. Crew red striped socks
Brooks Brothers argyle socks