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Should my socks match my underwear? Should they match my shoes?
OK – so I have gone through life not knowing how to match my socks. It is embaressing and scary – because what type of man doesn’t know this. Am I less of a man? Please help.

I think you meant this link:
http://artofmanliness.com/2008/01/23/rules-on-the-proper-wearing-of-socks/
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LikeDislikeOops — yes, that was meant for another question. Thank you for pointing that out!
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LikeDislikeRecently I tried to match my sock color to my shirt, tie, scarf, watch, pocket square or whatever other coloured item I wear. It may be a bit daring, and it violates the “classic” rule of having the socks match your pants or shoes (You may argue about that). But I find it to be classy, especially with striped socks. If you are uncertain (as I was the first time) just try it a few times and if you can honestly say to yourself in the mirror: Hey, I look like the modern gentleman, it is worth it.
Just google “colored socks with suits”, there are some great examples of style for more experienced gentlemen.
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LikeDislikeContrasting socks are great for more confident, experienced dressers — the Europeans have been doing it for years, especially Italian men.
As you mention, a safe default is always matching the color of the sock to the color of the trouser. As your wardrobe expands and you start to wear more colorful or patterned trousers, of course, this becomes harder and harder, and at that point it’s worth getting a few pairs of brightly-colored contrast socks!
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LikeDislikeClassic examples of contrasting socks include Fred Astaire and Gene Kelly (tap/jazz dancers WANT you to notice their feet and fancy footwork) and currently, David Boreanaz’s character on “Bones,” Seeley Booth. Booth wears the striped socks (which he likes in real life) and a skinny tie to add individuality to the field dress (dark suits) required by the FBI, as his character’s way of a little rebellion to the uniform. I occasionally wear contrasting socks in this manner, but pick up a color from somewhere else, i.e. Navy argyles with orange diamonds with an orange sweater, black socks with pink stripes with a pink dress shirt, etc. or, the classic 80s/early 90s, solid colored socks (yellow) with yellow sweater—it was popular, as a preppie, to match socks and sweater/polo in college. For more formal situations, I match socks to my suit/trousers, or shoes.
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