With summer in full swing, you can find shorts everywhere you look. Remember though, that a big part of being stylish is dressing appropriately, so it is important to recognize the situations where it may be better to keep your legs covered, despite the heat.
Shorts are, by nature, casual attire, though of course their level of casualness varies with each pair. Keeping this in mind, you want to make sure that they are the right choice for the occasion to which you are thinking of wearing them.
First, there are the shorts themselves to consider. Americans tend to have a problem with baggy, cargo shorts. It is generally one of the easiest ways to spot an American tourist, because we have a mindset that shorts, of any kind, are always appropriate attire. While it is true that a slim, chino-style short is going to have more versatility when it comes to dressing up, there is still a line of acceptability to consider when making your wardrobe choices.
Anything with cargo pockets, holes, fringe, patches, paint, or other embellishments are considered extremely casual and should be relegated to daytime activities, sporting events, or other leisure activities. I, personally, do not think that shorts are appropriate for anything but the most casual of occasions after sunset. I feel that unless you are going to a movie or a concert (popular not classical) or the beach after dark, there is always a better choice to be made.
Personal preferences aside, there are a few occasions where it is never acceptable to arrive in shorts. While I would hope that it goes without saying that formal occasions, such as weddings and funerals, are not short-wearing events, I have encountered guests showing up to weddings in cargo shorts, a knit shirt, and a ball cap. There may be rare exceptions, such as tropical-themed or destination weddings, but unless it is explicitly stated, please do everyone a favor and don’t wear shorts (even a tailored shorts suit) to any event where a tie is expected. Even if it may be tolerated you will only draw unwanted attention, which is never something that a gentleman desires (especially for an event that isn’t about you).
I would also suggest thinking twice before choosing shorts for the theater or going out to dinner- and by dinner I don’t just mean the jacket required kind, but really any planned dinner out at a restaurant. Casualness has become a real epidemic in our society, and I think it is important to try to bring back that sense of respect and class that comes from dressing appropriately for an occasion. When you show up dressed overly casual, it can convey a disregard for both the location and for those you are with.
That is why, despite many opinions to the contrary, I maintain that it is better to be overdressed than underdressed for any occasion. And if you discover that you are ridiculously overdressed, just keep in mind that, for all everyone else knows, you just have some place fancier to be later.