A Man's Guide to Wearing Shorts
Updated: Jun 3
Even in our modern society where you see every form of fashion on our cosmopolitan streets, the question of men and shorts still produces uncertainty among many. There is a reason for this that is embedded in our DNA. Until the early part of the twentieth century, shorts were worn mostly by young boys. A playful child was expected to run, climb and be adventurous. Putting them in long pants meant their wardrobe would need constant repair due to falls and skinned knees. A young boy was not in complete control of his body and not responsible enough to take care of the finer clothing. Moving out of shorts was considered a rite of passage in a boy’s life. It was not until he reached his teen years that he was allowed to wear long pants, thus, being viewed as a man. So, in our subconscious mind, we may sometimes view a man wearing shorts as someone that has not matured.
All of this began to change when shorts came on the scene in the early 1900s. A group of British soldiers were stationed in Bermuda, and due to the hot and humid climate of the island, they were allowed to cut off their military pants in order to help them tolerate the heat. It was at this point in history that shorts began to enter the fashion scene, but even then, they were mostly worn for playing sports or some other type of physical activity.
Today, men wearing shorts has become acceptable to our eye. There are guidelines every man should follow, though, so they do not come off looking childish.
1. Shorts are considered more casual, so they should be reserved for events with close friends and family. A day on the boat or a backyard picnic are good examples of places to wear shorts. Heading to a party with a bunch of strangers is probably not the best place to flash your kneecaps.
2. Wearing athletic shorts when doing yard work, playing sports, having fun in the park or going to the gym are obviously fine. Wearing athletic gear as a part of normal attire, though, is a habit worth breaking. I knew a guy who went to a popular local restaurant in our area one evening wearing a pair of athletic shorts. It just so happened he ran into the CEO of a small company he had just interviewed with. The guy readily admitted he did not put his best foot forward in the way he was dressed, and shortly after the encounter he learned he did not get the job. Assumptions were made as to why this was the case, but the consensus was, backed by some good intel, the boss felt if this guy would not represent himself well in public, how could the firm be confident he would represent them well in public. Remember my previous posts…image matters.
3. Shorts should never enter a business setting. There are two places in the world where this fashion rule can safely be broken, and that is South Africa and Bermuda. Because of the origin of shorts in Bermuda, the style quickly caught on for civilian men. In order to keep the more formal traditions of their British roots in place, though, they paired the shorts with a blazer, tie and knee-high socks. This beautiful British Overseas Territory is one of the only places you will see shorts worn in business, and if you ever have a chance to visit Bermuda, it makes for a unique, but special look.
4. If you do wish to wear shorts, I think the best look is a basic solid like navy, khaki or white. Most men look best in straight-legged shorts that end a couple of inches above the knee. Pair the shorts with a collared polo type shirt or short-sleeved button-down. Wear boat shoes or nice sandals, and you will look fashionably chic for summer.
5. Shorts should only be worn in hot weather. If it is cold out, why would you not wear pants? Just as it looks strange to see someone wearing a heavy coat in 90-degree weather, it also looks out of place to see someone in shorts in the middle of winter.
6. Generally, long pants are more flattering on men, so unless there is a specific reason to be in shorts, err on the side of a good pair of trousers.
Your image matters. When deciding if you should wear your favorite Bermuda shorts or a pair of cool, linen slacks, ask yourself which one represents the best “you.” You never know when you might run into your boss, or that business executive you are trying to land as a client. And as far as women go, most would prefer to see a man in pants, because, consciously or unconsciously, a pair of shorts reminds us of that little boy who would rather be climbing trees.
Together with you,