Sock it to me: When to and not to wear socks

Sock it to me: When to and not to wear socks

Q. I was at a cocktail party last night and nearly every man was dressed without socks. It was warm and they were generally more “fashion forward” than I am, but I didn’t think it was universally acceptable. Aren’t there rules on when to wear socks?

A. Yes, I would say there certainly are guidelines about when to wear socks. In the workplace (assuming you do not work on a dock or in a cabana club), socks are expected, if not a specific rule. In some offices it is a written or unwritten part of the dress code that some form of hose are required. Clearly, in casual and social settings, things are more flexible. 

While I do think your warm-weather cocktail party qualifies as an acceptable occasion for going sockless, the answer to your question can be approached in a few different ways. The easiest way to consider it is in a mix of first, footwear; secondarily, trousers; and finally, setting.


  • Sandals and Flip-flops are always worn without socks.
  • Sneakers are generally worn with some form of socks. No doubt, the reason is that sports activities commonly associated with sneakers, such as tennis, would cause rubbing, irritation, and perhaps even blisters if there were no cushioning from socks. But, since most men wear sneakers for non-athletics, they are more likely to wear them sockless.
  • Deck shoes are a category of shoes between canvas sneakers and leather loafers; they present the wearer with the option of wearing or not wearing socks. 
  • Loafers are the perfect leather “shoes” that offer the choice of whether or not to wear socks.  
  • Leather Dress Shoes: I distinctly dislike any traditional/conservative, classic type of dress shoes, such as lace-up oxfords, wingtips, and cap toes, worn without socks. The connection in my mind with leather shoes and bare feet triggers a strong reminder of odor! I’m sure that leather shoes would quite quickly develop this problem.
  • Boots conjure up the same reaction. They need some form of socks.  
  • Formalwear (black-tie and white-tie dressing) always worn with socks.  


Another way to approach the no-socks look is to consider what trousers are being worn. For the most socially palatable way to go sockless, choose slim, tailored trousers that create a modern, streamlined look. Be sure they fit well, they are not cut too full, and are not too long.

Cropped trousers (that is, shorter-than-usual trousers) have recently become a key piece of contemporary menswear. Ideal for wearing with a T-shirt, a polo shirt, an open-at-the-neck dress shirt, and with some fashion-forward suits, they pair well with smart-casual silhouettes, and work nicely both with and without socks . . . as long as the tops of your socks do not show. If you’re wearing cropped trousers or you’ve used a turn-up on your pants, sometimes the sockless look is a better choice than wearing socks. 

We generally think of the sockless look as seasonal, and if you are in hotter climates, opting for no socks is a logical option. These days, you are not likely to wear socks with shorts.


Which of two different types of settings you happen to be part of helps determine whether or not going sockless is acceptable. In much of the country, sockless is an unusual, even a strange, way of dressing. It looks unfinished and undressed, if not actually rudely inappropriate. On the other hand, in some Old School, upper-class circles, where preppy dressing is common, and also in urban areas where modern, fashion-forward, “shrunken looks” are in style, it is totally accepted in not-too-formal social settings. The truth is that it is a rather snobby/nonchalant way of dressing that works for the kind of guy who has lived his life around country clubs. 

The occasion/location is always something to consider. Places where going sockless would be totally appropriate include: barbeques, weekend errands, outdoor summer weddings, and business-casual offices. Places where the look would clearly be all wrong include: court appearances, interviews, board meetings, and funerals. You get the idea. 

Yet another major point to keep in mind: Wear invisible socks. There’s more to wearing shoes barefoot than meets the eye. Despite the seemingly effortless effect of going sockless, “no-show” or  “invisible socks” are an essential part of the puzzle. These low-cut socks allow you to look as if you are going without socks while actually wearing them. With many types of footwear, they are an ideal way to protect the wearer from irritation and help avoid sweat and odors while maintaining the stylish sockless look.

Still, this all comes down to personal preference. Some guys like the look, and some feel it looks undressed or pretentious.  A lot depends on your individual style.  Besides the occasion, choice of footwear and trousers, and the climate, your overall style plays a part in whether it works or not. 

If you’re more of a “dandy” or you take inspiration from Italian sprezzatura dressing style, you may enjoy wearing no socks on occasion. But if you have more of a traditional manner and you like to dress in the timeless style of a proper English gentleman, then you are likely to opt for socks. 

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