Q I just saw a man walking around a park in long shorts and a blazer. It looked weird. Is this ever appropriate?
A Do you mean, "Is this ever appropriate outside of Bermuda?" And, generally speaking, the answer is "no." We all know that men who live in Bermuda and men who are visiting there do wear long Bermuda shorts and a blazer, but it does come across as rather eccentric dressing when others do it elsewhere. Since a blazer is an almost dressy garment, and shorts of any length (even to-the-knee Bermuda-length) are casual, wearing the two together seems incongruous. If a man goes that next step and adds a necktie to the mix, to American eyes, it seems more like an almost-foolish costume.
The typical Bermuda shorts combination, which includes shorts, a blazer and knee socks, dates back to the early 20th century. British military officers stationed in Bermuda found that long trousers were too uncomfortable in hot weather. They were given permission to cut their uniform pants off, as long as some strict rules were followed: Bermuda shorts could not be more than six inches above the knee and they had to be worn with knee socks. They could be dressed up with a jacket and tie for business.
Of course, not all men's shorts are Bermuda length. Some that are shorter are still appropriate for street wear, as long as they are not too short. Nicely-tailored shorts can come across as a versatile way to dress, at either extreme end of the spectrum, whether quite dressy or very casual. In any warm setting, shorts of all lengths can be useful additions to a man's wardrobe, especially beginning at this time of year. If a man chooses a pair that fits well and if he color coordinates them with taste, shorts can be a welcome garment. Lightweight, cool and comfortable, they don't require a lot of thought and planning or a large outlay of money. When I see extremely expensive shorts shown in fashion magazines and in clothing ads from high-end stores, I wonder why anyone would think it sensible to spend sums exceeding $100 for a pair of cotton shorts or hundreds for linen!
There are options that are more appropriate than a blazer when a man is looking to make a handsome combination with shorts. One example might be dark shorts with a solid white or light-blue dress shirt; a second mix could be medium-gray or khaki-colored shorts with a quality knit, striped polo shirt; and a third choice could be white shorts with a short-sleeve sport shirt in a pastel plaid or tattersall pattern. A high-end, lightweight sweater or jacket pairs nicely with shorts of all lengths.
A larger concern than shorts being treated in a too-formal way, is the exact opposite: that is, men who wear shorts and look sloppy. For some reason, when wearing shorts, men sometimes think they have free rein to dress terribly with no attention whatsoever paid to color coordination or to an appropriate mix of garments. The same man who usually dress well in khaki pants and a colorful knit polo shirt or button-down dress shirt, often thinks nothing of mixing baggy khaki shorts with an old gray T-shirt that is stretched out at the neck. The two neutral colors do not work well together. And the result is a look that does not reflect well on the wearer.
My advice is to look for shorts that are neither too long nor too short. Avoid cargo pockets, cut-offs, logo T-shirts and other overly-casual touches. Try to find tops/shirts with a collar, thus, adding a touch of dressiness to the mix. People are wearing all kinds of combinations these days. Even so, if you want to look your best, aim for a look that neither includes a blazer nor seems as if you were dressed for mowing your lawn. You always want to be prepared to meet the world, even while informally dressed.
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