The answer is, well, complicated. Context is important here, and so I think it best to develop a clearer and more reasonable answer by telling the reader a bit about the situations that prompt me to ask the question myself.
I live in Scotland. It is a place that does not get much sun or warmth during the summer, but on days when the sun does burst through the clouds and the temperature does rise, it is absolutely beautiful. In some years, there are days and even weeks of continuous sunshine and warmth.
On such days, shorts are in order. But given the paucity of shorts—and summer clothes in general—in my possession, I try to be as interesting and creative as I can with what I have. Not a year goes by when I don’t consider wearing an outfit in which socks are at least allowable with the cargo shorts I am wearing.
Should you wear socks with cargo shorts? There is quite a bit of debate over this question among people who care about fashion. I have my own view. But before I give it, I will present the arguments of the contending sides.
How the Debate Got Started in the First Place
Socks should not be worn with shorts. This is a rule that started with elite aestheticians (who knows when) and got passed down over the years. For decades, the preppy young, yuppies, and other well-off young men followed this rule blindly, and it was adhered to by people who wanted to be part of that club.
The rule was justified as follows. Socks should not be seen at all. Your socks, it was further explained, should not even be seen when wearing pants. There is nothing to hide socks with shorts, so you must either forgo wearing socks with shorts or find no-show socks.
Exercising the latter option brings up another issue concerning style. When it is hot, humid, and unpleasant, most people like to wear as few clothes as possible, and want to give their feet access to the air. I tend to wear sandals with my shorts, and I suspect most other men do as well.
The only time you would think about wearing closed shoes with shorts is when the weather is warm but not hot, or you expect it to rain during the day. If the conditions are right to wear closed shoes with shorts, then you should also wear no-show socks. The latter can be found at nearly any retailer that sells socks and shoes.
They are designed to come just to the top of the shoe. This gives you the protection you want for your feet, but does not risk crossing the old-fashioned rule of the preppies. However, there are those who challenge this rule. Over the last couple of decades, people have been experimenting with shorts and socks combinations.
There is a line of thought that challenges the old rule on general principle. The people who adhere to it believe it is perfectly fine for men to wear socks with both closed shoes and sandals. They denounce the no-showing-of-socks convention as baseless and elitist. This belief is part of a larger trend in the “anything goes” climate of our current culture.
But is the Old Rule Still Viable?
In my view, yes. I would say that, in general, socks should not be worn with sandals and that no-show socks should be worn with closed shoes. In justifying this opinion, I can only re-iterate the judgement of the old school fashion aestheticians. Socks just look wrong and tacky with shorts and sandals, and showy socks are not much better with shorts and closed shoes.
There Are Always Exceptions
It is okay to make exceptions to the no-showing-of-socks rule. The times when visible socks are acceptable are almost completely arbitrary. However, these seem to be the most common:
1. When you want to achieve a sporty look
You can get away with wearing tube socks or athletic socks while wearing closed shoes and shorts if you are going for a fashionably sporty look. In this instance, your socks should be pulled all the way up with no scrunching. The socks should also match, as in complement, your shoes. Calf-high socks can accentuate the shape of your leg and make you look great.
2. When you want to go pastel
The other big exception to the rule is when you want to wear a pair of elegant cotton pastel socks. These cannot be worn with athletic shoes. Nor can you wear them with sporty cargo shorts. You can, however, wear pastel socks with chino shorts. You can wear pastel socks all the way up. It is also acceptable to wear them bunched up a little—no more than an inch.
Always Think About Your Shoes
Footwear is important here. The kind of shoes you wear determines the tone of your entire appearance. You need not wear athletic socks only when you go to the gym or for a run. You should wear white socks with white sneakers. If you wear colored sneakers for an outdoor workout, then you should wear socks that match them.
It is possible to wear them with sneakers even if you are spending the day on the town and want to be comfortable and casual. However, the kind of sneakers you wear on this occasion should signify that.
You should wear smart casual footwear with no-show socks or pastel socks. Wearing them with athletic or tube socks will produce a terrible clash. It will look downright silly. Finally, you should at all costs avoid wearing solid black socks with shorts.