I've been asked the question, "When is it appropriate to wear socks?" and have been pondering on this post for awhile now. There are so many weird things about socks, as cool as they can be, that it's not so easy to answer that question. Especially if you're not under the age of 30 and can get away with just about anything. That being said, I'm going to attempt to answer that question in the most honest and realistic way that I can. I mean, let's face it, we all have to wear them at some point or another. I think, it's more a matter of taste, style, and necessity.
If you are going to wear them for necessity, such as wicking away sweat, working out, keeping your feet warm, I do not think it matters what they look like as long as they do their job!
But, I do understand that there may come a time or place where this needs to happen. I mean, my mom wears trouser socks...many women do. I can't ignore it any longer. So, in this case I would say always match your trouser socks to your shoes. Black shoe= black sock. Navy shoe= navy sock. Brown shoe= brown sock. You get the picture. Make sure they're not bulky, or it will compete with your shoe and pant.
And if you're wearing an ankle pant, save the socks, please. Go with an ankle boot or go without. Unless you want to make a statement like this. In that case, by all means, have at it with anything you want! You will make a statement no matter what.
Hopefully that's slightly helpful. Socks can be so much fun, yet so boring when they're necessary. If you're in to making a statement any way you can, do whatever you want! If you're more concerned with how things look and making it just right, stick on the safe side. Either way, you're feet will be nice and cozy!