Hats for men are not as popular as they once were, especially the dressy kind, such as the fedora; but that doesn’t mean you can’t wear a hat and look good doing so if you choose. All you have to do is follow some simple style guidelines, and you should be fine.
The first rule of thumb when choosing a hat to wear, is that is really needs to reflect both your looks and your personality. For example a lot of bald men wear the “newsboy” hat to replace what nature took. This works fine so long as it fits properly and the colors or color pattern go with what you normally wear. On the other hand, a lot of guys lean towards the baseball cap, either an actual replica, or one that is made in the same style. While the baseball hat works fine in certain environments, there are many others where it does not; particularly if worn backwards. A good rule of thumb to follow here is, only wear a baseball cap if playing baseball or doing something else that requires you to be out in the sun for an extended period of time, because baseball caps don’t really look very good anywhere else.
Other hats only work for men that have a certain look; the trilby hat for example, as worn by many celebrities of late, seems to work best when worn by men who possess a certain panache, or flair for fashion or design. In a similar vein, the cowboy hat only works if you have a very definite cowboy look and attitude. Otherwise it looks ridiculous.
Something else to keep in mind is that there is a difference between wearing a hat as a functional item of clothing, rather than as a statement of style. Though, there are times when the two can intersect; the beanie hat is one example of this. Since there are so many variations on this one style, such as the knit, skully or even stocking cap, it can become a very unique fashion statement, even though its original purpose was simply to keep the head warm when it was cold outside.
There are also certain occasions where a style of hat will work, but other times it will not. A top hat is an example here, and so too are the Fez, tam, bucket, Panama or porkpie hats. These are all meant for certain occasions and wearing them at other times very rarely works.
Other hats though can be worn by almost anyone because they are low-key and demure. The fedora and the bowler are good examples, thought he wearer should keep in mind that these hats are for the most part only to be worn when outdoors.
The bottom line is, if you are a man who is considering a hat, take a look first at who you are and what you look like. Doing so will allow you to choose the kind of hat that will make you look better, rather than worse.