Should my socks match my pants or my shoes? This is one of the most common question men ask. The answer is simple. Socks should always match your pants, never your shoes. One of the goals when wearing socks, besides protecting your feet, is to elongate the pants silhouette. If you match your socks to your shoes, you are creating an impression of a bootee, which just looks weird.
Matching the colour of your socks to your pants is generally simple. If you are wearing black trousers and you pair them with plain black socks, it's a very safe choice. Your next step towards style would be to move from a plain black sock to one with a ribbed or patterned texture.
Plain black is a boring, albeit safe, choice. Matching your socks to your pants does not mean finding the exact shade of burgundy to match your chinos. It means finding a tone of burgundy and putting it together. It means picking up that burgundy tone in a pattern. It can also mean finding a sock that is completely different and matching it with your shirt or your blazer. Once the outfit is assembled, it should look styled and pleasing, not garish.
Any ensemble you are wearing, for any occasion, will be made more stylish and individual by the addition of some interesting colored or patterned socks. Consider your work wardrobe for a moment. A charcoal suit, a black suit, a navy suit. Chinos, shirts and blazers. Various dress shoes. Besides the option to wear a coloured shirt with your suits, you should be adding flair with your socks.
Formal pants, as with your casual pants, should be well fitting. If your pants are too tight or too baggy, it looks awful and ruins your look. If you struggle to find pants off the rack that fit perfectly, please find a tailor and have them custom tailored. The current trend is to wear narrow leg trousers with a cuff or, for chinos, with the hem folded up a couple of times. This gives the opportunity to flash those quirky socks and keep it interesting.
If you are not comfortable yet with bright socks, try combining a navy trouser and brown shoes with a lighter royal blue sock that matches the colour of your tie. Of course, you could go all out and keeping the same basics, wear red socks and match it with a red pocket square for a bit of panache. To change it up more, add socks with a bolder argyle or large spots in varying shades of blue and turquoise.
For those occasions that call for less formal clothing but you still need to look sharp, like a date or meeting the parents, you can opt for coloured chinos or dark blue jeans. Again, well-tailored is the key. Confidently don your yellow patterned socks with your jeans and your favourite penny loafers and you will win the night.
Choose a color or combination of colours that you know works for you. Start with the safest choice and gradually move out of your area of comfort until you are confidently striding along with elegance and color.