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A Man's Guide to Wearing Shorts

Today, where we see every form of fashion on our streets, the question of men and shorts still produces uncertainty among many. There is a reason for this that is embedded in our DNA, and to fully understand we need to explore a little history. Until the early part of the twentieth century, young boys exclusively wore shorts. 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 boy was not in complete control of his body and not responsible enough to take care of finer clothing, therefore moving out of shorts and into long pants was a rite of passage. Shorts were for little boys and pants were for young men. Thus the reason subconsciously we may 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 to help them tolerate the heat. It was at this point in history that shorts began to enter the fashion scene, but they were mostly worn for sports or some type of physical activity.

Today, men wearing shorts has become acceptable to our eye, but there are still guidelines men should follow so they do not end up sending the wrong message.

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 when to wear shorts. Heading to a party with a bunch of strangers is 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 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 from an inside source he had been passed over for the job. Assumptions were made as to why this was the case, but the consensus was 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, our image matters.

3. Shorts should not be worn in 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. To keep the more formal traditions of their British roots, though, they pair the shorts with a blazer, tie, knee-high socks, and dress shoes. This beautiful island is one of the only places you will see shorts worn in business, and if you ever have a chance to visit you will enjoy seeing this unique, but special look.

4. If you do wish to wear shorts, the best combination is a solid color like navy, khaki or white, and a collared shirt. Most men look best in straight legged shorts that end a couple of inches above the knee. Pair this with a 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 be reserved for hot weather. If it is cold out, why 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. 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. And always remember, the more we mature the more formal we should dress.

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 subconsciously, a pair of shorts reminds us of that little boy who would rather be climbing trees.

Together with you,

Lisa Lou


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