Socks match your pants
First off, the traditional. This is the place where your socks are made to match your suit/pants/denims/trousers. This is a tricky one because that makes for boring socks. No one wants a boring sock. There are a very limited number of colours that allow you to branch out when you're matching sock to pants. Mostly you'll end up wearing brown, black, blue or grey socks. What you really want is colourful socks that peep when you're sitting and this approach of pants to sock just won't allow for that. This obviously changes if you're the type of person who likes to wear pink polka dot pants. Then you've got a whole lot of choice in front of you. It's also very important to consider what shoes you choose to wear, in order to complement the pants and socks you're wearing. Wearing black pants, black socks and then choosing a brown shoe will most often not work (there are exceptions to the rule, of course).
To summarise: Socks can match pants but be careful of your shoe choice.
Socks match your shoes
Historically this has been shunned as a no-no for a very simple reason. You don't want to appear to be wearing a single-coloured booty or Ugg-looking situation. You're an adult. Not an adolescent teenager or toddler wearing booties. But things have started to change. It's important to define what is meant by the word "match" in this scenario. We don't want you to be wearing a blue shoe and a blue sock with blue pants (unless you're really going for it). You could perhaps wear denims, with a blue and red sock and a shoe that has either blue or red in it. You're highlighting colours, not matching them.
To summarise: If you're matching shoes and socks, highlight colours, don't match solid colour socks to solid colour shoes.
Socks match your accessories
This is the new way forward and a brave way it is. Men and women all over the world have decided that it's time to wear colourful and fun socks. There are two ways to do this. Firstly - You can get over the concern about matching and wear whichever colourful sock catches your eye when you get dressed. We like this option and generally for us, dressing starts from the ground up. We build our entire day from the feeling of joy when we put on our loud, happy and comfortable bamboo socks. Secondly - You can plan to match your socks to your accessories. Things like your ties, pocket squares, the cuff links you're wearing, the inner fabric of your jacket, the shoe laces on your shoes are all viable matching alternatives to the shoe and your pants leg. Do not go gently into that good and boring trap of tradition. Step out of the norms and match your socks to whatever the hell you want. But be sure that there is some intention behind your choice, even if it's just to look crazy and feel good on a Monday morning.In short, you can match your socks to your pants, you can highlight colour in your shoes by wearing a corresponding sock or you can just forget it all and wear an accessory that you'd like to match your socks to. Deep down we don't care whether you're matching your sock to your hair colour or to your underpants as long as you're not wearing boring socks but rather choose colourful socks, every time.