Socks are a complicated subject for a number of reasons. Do you match your socks to your pants? Your shoes? Your tie? Your belt? Your shirt? Do you need your socks to match anything at all? How loud or quiet should socks be? Are there hard and fast rules for which socks to wear when you are dressing classy?

Some pretty "out there" socks ya' got there!

Let me just say right away that for me socks are an afterthought as compared to shoes, belts, ties, or suits. And there is a simple reason for that: socks are less important to my wardrobe than all those other items. Can they add a ton of pizzazz if done properly? Sure. Can they kill my look if they are way off the mark? Yes, for sure. And they are therefore definitely not an item of clothing that you can ignore. Now, I used to always play it safe (I’ll explain what that means later in the article) and not think about them too much. But I realized that I had definitely been missing out on some fashion opportunities when playing it safe, so I’ve started to experiment with some more sock-ual flavors, and here’s what I’ve learnt.

Playing it Safe

Most people (like the old me) will find that playing the sock game safely is the smart way to go. How do you play it safe? Follow these 3 simple rules:

1. Matching: Do not ever, ever, ever match your sock color to your shoe color. Just don’t. You can literally pick anything else to match it to and you will be fine 90% of the time. You can match it to your pants, your tie, your shirt and even your hat if you are so inclined. All of these options will work and still keep you classy. But if you match it to your shoes then you will almost always ruin your look. Why? This is a simple one: If your socks match your shoe color then it will look like your socks are an extension of your shoe resulting in the classless “bootee” look. (On the flip side, matching your socks to to your pants color will result in your legs looking longer, and you looking taller.) Trust me. Steer clear of matching your socks to your shoes.

Perhaps the most classic length for men's dress socks

2. Style: Go with solid, darker colors. This is probably the most controversial rule of my “playing it safe” rules. This really falls under the “playing it SUPER safe” rule. But if you are not great at coordinating intricate patterns and colors, then just follow this rule and you won’t mess up.

3. Length: Opt for the mid-calf or knee-high sock. Remember, this section of the post is dedicated to “playing it safe.” So, it should come as no surprise that I strongly recommend wearing higher socks. The main goal of the high length is not to show any skin (there’s nothing worse than seeing your leg hair stick out when you sit down and your trouser leg rides up). But there’s also an added benefit that the higher socks tend not to roll as much as lower-cut socks.

Being Risqué

Hey, even if you play it safe most of the time, there is still some room to show some creativity with your sock-wearing here and there. Listen, definitely don’t pull out your risqué moves when you are going to an important meeting or if you have a serious interview. On those occasions, follow our rules above. But, otherwise, here are 3 ways that you can add some flavor to your classy sock wearing:

1. Matching: No need for it. Socks can speak for themselves sometimes! Matching your socks to something else in your wardrobe (above your ankles) will always work well, but it’s not strictly speaking necessary. You can wear socks that don’t match anything else and still look great. There’s only two things you need to be careful with here: (1) Make sure your color choice doesn’t clash with something you are wearing. For example, if your pants are a light blue, don’t wear black socks. (2) Don’t wear too many colors. As a rule of thumb, keep it to 3 or 4 different colors at most.

See? Your socks don't need to match your pants or shoes per se.

2. Style: Add some patterns, ribbing/texture and some lighter, solid colors.

Patterns: Personally, I find this the most difficult. Once I add patterns, things get complicated. I like spicing it up a bit with a basic polka dot or striped sock. This is still easy enough not to mess up. But you can definitely get more interesting with patterns — like argyle, fair isle, marled, and so on — without ruining your classy look.

Ribbing/Texture: This is actually not so risqué at all. Some simple ribbing can really go a long way to adding style to a basic sock. It’s not loud and the subtlety is really nice. I considered putting this in the “playing it safe” section, but hey, I figured I’d make you feel edgy even if all you do is wear a solid, dark, but ribbed sock.

Lighter, Solid Colors: I recommend this with some caution since if you go too bold you can really stick out like a sore thumb and ruin the rest of your outfit. So, tread carefully here. However, to be honest, a nice, bold, toned, solid sock can make you look INCREDIBLE. I’ve seen this look pulled off a couple of times, and I goddamn love it. High risk, high reward.

3. Length: Still go with the mid-calf/knee-high sock. Yeah, you were expecting me to tell you that sometimes it is okay in a formal setting to go with ankle or no-show socks. Well, sorry to disappoint. Formal and classy outfits (i.e., some sort of dress pants and dress shoes) require you to wear higher socks. I get that some people can still rock the classy look without wearing socks at all! But it’s a really hard look to pull off when you’re staying classy. Thus, I recommend that you avoid it even when you are feeling more risqué.

Conclusion

You can either view your socks as an item that you just don’t want to ruin the rest of your wardrobe with, or an item that you want to use to take your wardrobe to the next level. We gave you some basic rules on how to do both. For those who want to play it safe, don’t match your socks to your shoes, keep your colors and patterns simple, and you won’t go wrong. For those who want to show some personality, socks are definitely a great way to test the waters.

Lastly, for those of you who want to start getting a more advanced knowledge of socks, keep an eye out for a future article wherein we will give you some details about the various sock fibers and constructions and how to properly care for your socks so that they last for a longer period of time (hint: socks have short life spans no matter what you do).