Dressiquette – Your Socks Should Match Your Pants

Weirdly enough, there is a lot of debate out there regarding whether your socks should match your shoes, or whether they should, in fact, match your pants. Now, before we get started, I know there is a lot of leeway when it comes to choosing a pair of socks. Some gents choose to shoot the lights out with brightly colored socks while some prefer to make a statement in socks that look like hot dogs, others (myself included) choose to forego socks completely and flash those ankles all year round. We’ll get to all of that in just a moment.

This post is more about tradition. The ‘correct’ way to wear your socks should you find yourself in a situation where hot dog socks are frowned upon – which really is anywhere other than behind a hot dog cart!  So, after much research, and much disagreement it turns out, there is no simple answer! Surprise! I am happy however to report that the general consensus is “your socks should match your pants”. There you have it – feel free to stop reading now if you were just looking for a quick answer.

The thinking behind this rule is pretty simple. All that you’re really trying to do is create a seamless transition from the hem of your pants to your shoe so as not to create an unsightly break in color when your pants sway to your general sashay! This is the primary rule and should really be applied wherever possible. In situations where you’ve splashed out and picked up a pair of cerise pants but failed to find a perfectly matching sock, then feel free to match your socks to your shoes.

My personal advice is unless you are going somewhere incredibly formal (like tea with her Royal Majesty the Queen) I would forego this rule all together! A formal event will generally call for black pants and black shoes anyway so, in the end, it’s a no brainer! If you start forcing the matchy-matchy rule your outfit may end up as bland as the grey blur above!

If you’re going to insist on socks, then try to have some fun with them! No, I’m not condoning hot dog socks – You should never confuse novelty with fun. As a general rule, I suggest staying away from novelty anything, socks, ties, bow ties, pocket squares, etc.

Having some fun with your socks just means not taking the above rule too seriously. Let the break in your pants and shoes convey a little of your personality. In my opinion, a solid color goes a much longer way in making a statement than a pattern ever does. You can, however, kill 2 birds with one sock by picking something that brings a little more fun further up the sock. I picked up the socks above from Paul Smith a couple years ago and they’re still my go-to when I decide to wear socks – which really isnt often : )

Final tip: If you’re going to break the rule, break it hard! Make sure you create enough contrast between your socks and pants (or shoes) to make the choice seem purposeful. If the color or tone is too close to either it will seem as though you were trying to match them and failed, so err on the side of boldness here! Heck, ALWAYS err on the side of boldness when getting dressed! Lifes short you know.

If you’re looking to avoid sock confusion all together I would strongly suggest my personal favorite, the ankle…or “European sock” as I call it. Those of you who follow our Instagram feed will already know, I’m not shy to show a little skin around the ankles and wearing socks is often the exception that proves the rule – or is it the exception to the rule, I never know the difference.

There’s just something about that skin break that takes your look from business to badass. It takes the edge off and brings a nonchalance that shows you don’t take yourself too seriously, regardless of how perfectly put together your outfit is! I get a lot of flack for this on Instagram…but it’s generally from people who post pictures of crossbows so it doesn’t bother me too much! We’re not here to conform, right?

The secret to a good European sock is, in fact, a good secret sock. That’s right, I’m certainly not telling you to go sockless because…well…gross! I’m constantly on the search for a good secret sock and so far found that Pair of Thieves makes some of the best (don’t worry, they’re not paying me to say that). You have to go for a ‘no-show’ sock rather than a low cut sock or training sock, the slightest show of sock will ruin the entire look. This is especially important when wearing loafers as they are generally lower cut and tend to peek out on the sides. When it comes to loafers I’ve found that women’s stocking socks (yep, I said it, I wear women’s socks) work the best, they are generally very low cut as well as flesh-colored so they’re almost invisible – I picked up some amazing ones with a cushioned sole at Primark in the UK and they are an absolute winner!

Last tip for that European sock, don’t make the mistake I’ve made and buy the cheapest socks you can find. As my dad always says “You buy cheap you buy twice”. Go for a quality cotton sock that is breathable and cushioned on the sole. You’re also gonna want to pick up something with a non-slip rubber inlay on the heel to stop your socks slipping down into your shoes! Trust me on this.

Okay, wow, who would have thought there was so much to know about socks right?

Okay. Stay fancy.