My hard rule about dress socks: show no skin. For some reason, the majority of dress socks I see in stores are really crew socks that don’t cover the calf, causing the socks to slide down after taking a few steps, showing the world a little leg when we sit down.
The simple solution is to find smart man hosiery that is long enough, like Gold Toe® Over The Calf socks. If you have some great looking pairs of mid-calf socks you love, the other solution is to wear sock garters. (Yes, I have a pair.)
Whimsically striped or colored socks in a casual setting are a different story. For some reason – and this is just my opinion – I think it’s okay when a handsome pair of colored or striped casual socks slide down and reveal a little leg under jeans, chinos or other casual trousers. Sort of charming, in fact.
But when it comes to proper formal, semi-formal or business attire, the only skin we should see should be above the collar and below the wrist.