Good Fit Guides
Wear dress socks with dress shoes
Don't try to wear athletic socks with dress shoes even if the socks are black. Athletic socks are thicker than dress socks and don't match the refined style of dress shoes. If you try wearing gym socks with a pair of dress shoes, they'll bunch out over the shoe and look bad. Stick to dress socks. The thin material feels nice on your foot and looks sharp.
With jeans there's a little more wriggle room. Preferably, you should have dark socks even with denim, but you can get away with wearing gymn socks with jeans.
Sock color should match your trousers, not your shoes
This is a rule that many people are confused about. We hear many different arguments about whether you should match socks with shoes or socks with trousers. You should always match socks with trousers because when you sit down and your socks are exposed, you want a solid line of colour from your trousers to your shoes. Socks that don't match your trousers' colour create a jarring break in your outfit. So black socks go with black trousers and brown socks go with brown trouser. Absolutely and under no condition should you ever wear white socks with dark trousers unless you want to look like a 1980's Michael Jackson.
No socks with sandals or shorts
The weirdest thing is to see people who wear socks with sandals. Society's ability to take you seriously will be drastically diminished if you do this. Sandals were designed to be worn with bare feet, so please, do not wear socks with sandals.
Socks with shorts should be avoided as well. Wearing socks with shorts visually makes your legs look shorter. If you need to wear socks while wearing shorts, invest in some ankle socks that aren't visible when you wear you sneakers.
Novelty socks are for not for you!
No man should own a pair of orange novelty socks that say "Boo!" on them and are adorned with little bats. The only excuse you have for wearing these is if you're a kiddies school teacher named Mrs Heart. Keep your sock collection simple and classic and you'll never go wrong.