Okay, maybe you wouldn't want to wear a pair of brightly-colored men's socks to a funeral, but aside from that, there's no reason why you should shy away from fun socks! Men's socks, for the most part, are pretty nondescript. Aside from a more expensive pair of socks being sewn a little better or having a slightly better quality fabric, it's basically a matter of "you've seen one pair, you've seen 'em all"!
A fun pair of socks is a great way to express your creativity and individuality. When we sit down and our pants' legs hike up a bit, it's a nice surprise to see a fun, colorful pair of socks instead of a drab gray, black or brown. Women appreciate a guy who's not afraid to be a little different, who doesn't mind standing out from the crowd. It shows a certain confidence and says something about his personality too -- he's definitely not stuffy or overly serious.
We're not talking about changing the world, here. Nobody's suggesting you should go to work in a Hawaiian shirt (unless it's "casual Friday" at the office). We're talking about making a little statement with a simple, stylish pair of socks. They'll add a little flair to your staid gray business suit, or an unexpected burst of color under your jeans on the weekend. It's actually a pretty modest way to say that you make a little effort to inject some fun into how you present yourself to the world and how you feel about yourself in general -- confident and self-assured.