How To Go Sockless Without Looking Gross

I’m going to give you guys a cold hard dose of reality. Your ankles are not attractive. If you habitually go sockless your coworkers talk about you behind your back. And more than a few of them think it’s kind of gross. And that group of people undoubtedly includes women. Never in the history of the world has a woman thought “wow, I bet his ankles are so sexy! I wish he wasn’t wearing socks!”

In the pre pandemic world I would commute into NYC and see the same people on the train platform every day. Even if it was 20 degrees and snowing one particular guy was always sockless. Overcoat, hat, suit, the works. But no socks! It was so strange and incongruous with the weather and the rest of his attire that his fleshy ankles stood out like a beacon. Don’t be that guy.

Now, there are times when going sockless is ok. There are instances where if you forgo socks you will not be viewed as the weirdo with the stinky shoes. Here is how to go sockless without looking gross:

Right kind of shoes: First and foremost, make sure you pick the right shoes with which to go sockless. Boat shoes, loafers, espadrilles, and canvas sneakers (like Mr. McQueen above) are all acceptable for going sockless. Do not, under any circumstance, go sockless with dressier shoes like oxfords. There is literally never a good reason to forgo socks with oxfords. You won’t look rakish and sprezzy; you’ll look like you forgot how to dress yourself properly. Socks provide visual continuity between your trousers and your shoes. If you’re not wearing socks that continuity is broken which will cause everyone to stare directly at your feet. Why do you think Gene Kelly and Michael Jackson wore white socks with dark shoes? They wanted people to look at their feet. Going sockless has the same effect. Is that really where you want people to look? Wouldn’t you much rather they look at your face? If you’re wearing oxfords or some other dressy lace up shoe you are most likely wearing a suit or some other form of conservative leaning menswear. You want to be taken seriously. Don’t muck it up by not wearing socks. And don’t give me “but I get too hot!”. You’re already wearing dress shoes, trousers and possibly a jacket. The socks won’t make a difference.

Keep it casual: If you follow the first point and only go sockless with the proper shoes, then this point will seem redundant. But it bears mentioning. Sockless should be easy and breezy. Chinos, linen shirt, loafers = fine to go sockless. Trousers, spread collar dress shirt, tie, pocket square, cuff links, jacket = NOT fine to go sockless. It takes effort and care to dress more formally. Going sockless jives with the whole “oh I just pulled this on” sentiment of casual wear and clashes with the detail-oriented intentionality of more formal wear.

Make sure it’s summer: Or hot enough to be mistaken for summer. Going sockless should seem almost like an afterthought rather than a conscious decision. Like, “oh I just slipped on my shoes to head out the door and I was already not wearing socks because it’s hot out.” In the cooler months you probably would have to remove the socks you’re already wearing (because it’s cold) in order to specifically “go sockless” which will come across as trying way too hard. You’ll stand out in a bad way.

So there you have it. If you abide by those 3 points above you will most assuredly not look gross the next time you leave the socks in the drawer.