Good question from a good reader.

I recently purchased some nice dress socks to help my transition to a more masculine me…the only issue is they seem to only have two sizes of socks. The socks that fit shoe sizes 6-12 is the size i fall into since I wear size 9.5-10.

Now that is fine and dandy, but when I put the socks on, the formed heal of the sock always ends up clear up at the top of my ankle. To me this looks a little sloppier than my faded ugly socks. Can you do a post of shopping for, selecting, and wearing dress socks to help us clueless men out there that don’t know what to do in this situation?

Thank you,
Tyler (a clueless man)

What Tyler’s talking about here is a fairly common, albeit small problem. It’s much more noticeable when the heel cap of your sock is very different from the rest of the body, but still obnoxious when you notice any difference.

There are basically two approaches to solving this problem. The first is to immerse yourself into the world of luxury men’s hosiery. There are companies (Zimmerli) that will offer cashmere socks to specific foot measurements. However be prepared to pay the price; they’re not anywhere near cheap.

The second option is much more preferable – change the way you put your socks on. Since Tyler asked about dress socks, I’m going to assume he meant anything over the calf or at least mid-calf as ankle socks are inappropriate for business situations. 99.9% of men will put on their socks the same way – grab the opening with both ends, insert foot into opening, and pull sock all the way up as high as it goes. It’s simple, efficient, and keeps the top part of the sock over the calf preventing it from falling down throughout the day. However, even if your foot is the perfect size for your one-size-fits-all socks, by having the stretch begin at the toe cap and continue all the way to the top of the calf, you’re bound to have the heel cap stick out of the shoe.

The best alternative is to split that two-part process in half. When you first put on your socks, only pull them on as far as covering your foot. From there, you can either simply step on the ground or put on your shoe and then pull the upper half of the sock up and over your calf. By having the stretch start at the heel instead of the toe, you’re able to keep the heel cap in place and hidden inside your shoe.

This process is easier with over-the-calf socks than their mid-calf brethren. Most of us know intuitively that the higher the sock sits on our calves, the more likely it is to stay in place. Since mid-calf socks don’t sit as high, you will have to overcompensate by having the stretch begin from the toes.

From a comfort perspective this does take some getting used to at first. The lower half of your sock won’t be stretched as tightly over your feet and will feel a bit baggy until you get used to it. Just remember that you’ve trained yourself to recognize that stretched feeling as normal when it really isn’t.

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