How to pick the right dress socks and up your business fashion game

Dress socks are the key to looking sharp while adding some flair to your outfit. Here's how to pick the right ones.

Dress socks are all the rage these days. Once a utility accessory coming in dull shades of grey and black, they’ve become a place to add some flair and class to your business attire. There’s even a secretive London sock club whose mission is to “elevate and champion men’s hosiery,” and their proceedings are about as mysterious and elite and Fight Club. I want to put this frequently missed style opportunity to the forefront of the minds of our greener readers, too. If everything in your sock drawer has a label that boasts “sweat wicking ability,” features a Nike swoosh, or came in a 6 pack on sale from your local department store, then please, read this.

The first thing to consider when upping your sock game is materials. You wouldn’t show up to work wearing a pilling wool sweater, so why should your standard for socks be any lower? Not unlike most other garments, superior materials such as cashmere, wool, and comparable blends are all the best choice when selecting a quality sock to wear outside of an athletic environment. In the world of sock selection, a blend can be the key to having a comfortable sock that will feel fresh during a busy day of bouncing from morning meetings to client dinners. Consider how long you’ll have to be wearing the sock, and opt for something that has wicking materials. Admittedly, these materials may not be all natural fibers, but they’re a necessary evil. They allow for airflow and can protect from blisters, etc., by keeping your feet cool and secure in a new, stiff dress shoe.

Happy Socks Faded Diamond
Happy Sox Faded Diamond Sock ($10.00)

Who knew socks could be so hotly debated? A common question is whether or not to wear bold colors and attention grabbing patterns in a formal setting. The jury seems to promote independent thought in this area. That is to say, if you can own it, go for it. In a pair of tailored pants for work, chances are that the hem of your bottoms extends past your ankle, reaching your shoe and covering your sock. So, there is little occasion for the sock to be seen while standing, and limited possibility while seated. This plays to my argument for being bold. You can still make a serious first impression, and you’ll give those with a keen eye a little something to talk about. Of course, gauge your audience. But don’t be shy. If you so dare, select a sock that matches the shoe and the color of your suit. This doesn’t have to be an obvious match, but to avoid the Michael Jackson clash of white and black, consider the sock part of your outfit’s color palette and blend accordingly.

Ayame Socks
Ayame socks in various patterns ($25.00)

One last thing to consider, though certainly not the least important, is the height and fit of the sock. For a business setting, avoid showing skin at all costs. Your trousers will appear ill-fitting if your socks are low enough that your ankles or calves flash occasionally. So, no ankle socks in the boardroom, please. Try something that reaches to just below the calf or higher to make sure you’re well covered. (As an added bonus, this is great for your circulation if you’re sitting at a desk all day.) Especially when dressing for fall and winter, high socks are a stylish functionality. Be sure to note the size guides for your brand of choice too, so you don’t get stuck struggling to stretch the sock around your oh so chiseled calves.

Pantherella Naish long socks
Pantherella Naish long socks ($30.00)

There are a few great services to break you into the deep world of sock selection if you’re a newbie. Subscription services abound, like Sock Fancy, that deliver the latest to your door monthly. Many of its kind have been gaining buzz in the recent past, which is a sure sign that this niche is not to be overlooked when dressing to impress.

Nicole Edwards

Nicole Edwards is a fashion and lifestyle writer based in Toronto. She has worked as Associate Publisher of Private Islands magazine and Lifestyle Editor of Style Empire, and has contributed to NOW Magazine.