I recently professed my love of socks, one of the things that I have a zillion of and can't stop buying. Eventually, you get to a point where you have some in every color and pattern, and it can seem a little daunting to pick out a pair that doesn't clash. Sure, they might be covered by your pants most of the day, but those times that they do flash, you want the proper effect.
And that's really what it comes down to. What's the effect that you want? You really have two choices. The first is definitely the most basic. You just want to match. You don't want to stand out, you have no urges to inject your look with a pop of color, you want to be stylish but unobtrusive. If this is your motivator, simply pick socks to match your pants. A lot of people waiver between matching their pants or matching their shoes, and let's end that hesitation here and now - always match your pants, never your shoes. By matching your pants, you make your legs look longer, which is a good thing for 90% of guys out there (that's an exact statistic, by the way). Comparatively, if you match your shoes, your legs can look cut off at the ankle. Also, if you're wearing some snazzy kicks, the lack of contrast between your footwear will make them far less likely to shine.
|Thompson Chino Suit Pant in Navy paired with Basic Crew Socks in Navy | J.Crew Factory|
The second effect is to show a little pizazz around the ankle...whether it be that pop of color, a flashy pattern, or even some subtle texture. I'm sure there are tons of methods to doing this, but my personal method is to pick a part of your upper outfit (above the waist), and try to play off that piece. This may be your shirt, your tie, even something as small as a pocket square. This is a great way to really make your outfit a whole, with correlation between the top and bottom halves. There's not necessarily anything wrong with it, but it's very easy to have one outfit from the waist down, and another, not necessarily clashing, but unrelated outfit from the waist up.
However, you do NOT want to match exactly - a faux pas almost as bad as wearing a matching tie and pocket square. Instead, compliment. An easy way to do this is to match solid with patterned, and vice versa. If you have a patterned tie (or pocket square, or shirt, or whatever you are trying to match), pick one color from that pattern, and match it with a solid sock. If you have a solid tie, go ahead and rock a patterned sock that shares one color with the tie. Once you are confident in your pattern matching, go ahead and mix things up, but be careful not to get too out of hand and risk looking clownish. This is your clothing, not a costume.
|Summer Plaid Tie (patterned) paired with Basic Crew Socks in Navy (solid) | J.Crew Factory|
|Red Chambray Tie (solid) paired with Triple Stripe Socks (patterned) | J.Crew Factory|
Bonus Tip: The scale of the pattern tends to be directly proportional to the casualness. Pin dot socks, or fine stripes, perfectly OK for business attire. Large polka dots, rugby stripes? Probably best kept to more casual occasions.
OK, after giving all that advice, I just gotta say, socks are a great place to stretch your sartorial wings, largely because they are so low-risk. They do stay hidden most of the day, so if you experiment a bit and it doesn't work out, you're not going to be running around looking like a fool all day. So have some fun! Try something new!