It’s hard to believe, but shorts on men are a relatively modern convention, popularized in the 1950s and 60s. Before that, in the late 19th and early 20th centuries, shorts were strictly for boys and often called “short pants” or “knickerbockers.” During World War II, soldiers stationed in the tropics were issued shorts to keep them cool and also to ration cloth. In the post-war years, shorts were worn for recreation, but men would swiftly change out of them after playing sports such as tennis.
Nowadays, shorts are an acceptable wardrobe staple, but it still pays to know when to wear them. The two things to keep in mind are the weather and the event. Break out the shorts only when it’s hot and when the occasion isn’t formal or business-related.
How long should they be? The best rule of thumb is that your knees should be showing, but don’t go any shorter than two to three inches above the knee. You don’t want to show off your lily-white thighs, do you? The only exception to this rule is running shorts, which can be shorter, but make sure you change out of them and into something longer before socializing.
As far as style, avoid anything too baggy, which will make your thighs and rear end look big. A close fit in the seat and straight legs down to the knees is flattering on most men. Beware baggy “cargo” shorts that have a lot of pockets. They are great if you’re hiking and actually need to carry a lot of stuff, but they aren’t the best choice for social settings where you want to look polished.
Lastly, when it comes to footwear, shoes that slip-on shoes like boat shoes or loafers are good choices and can be worn without socks or with “invisible” socks that won’t show. Of course, great sneakers work well with the look too.