I think wearing socks with sandals depends on the situation... take for example we all like going to the movies but they can be quite cold. Therefore, if you are wearing sandals and are prone to feeling even the slightest drafts, it spells the spoiler for a great movie since you concentration reduces drastically in a bid to try and keep warm.
Thus in such cases bringing socks with you to the theater seems like the logical option to having a great movie night then remove them after, and if you happen to be on a date it spells for a good conversation starter.
On the other hand we cant ignore the fact that winter doesn't provide much of an option for not wearing socks. However fashion has provided a way to still wear socks and looking good while at it especially for those whose opt to pass on Ugg boots. This however only works with slip-on sandals that don't have the thong design common on flip flops since it makes wearing them look tacky for the lack of a better word. Furthermore investing in socks with color similar to those of your slip on sandals helps camouflage the socks
and you can go about your business feeling confident rather than being self conscious of every look you get.
While i am on this referring to my earlier post how you color coordinate everything goes along way to determining how comfy you feel when you venture out beyond your front door.
Remember jeans have always been and will always be that fashion piece that wont ever go out of style decade in decade out therefore when in a bind...wear jeans...with any top and a handbag to match the sandals but if there is no handbag a top can still do the trick. with the right jewelry the focus is drawn more to your face rather than to your feet....and in most case your feet become the focus if you have either hit the fashion jackpot or if their is nothing upsides to keep the focus on you.