In previous decades, the idea of men's fitted hats was a tautology, because of course a hat was bought or made to fit exactly to a wearer's head. While it's certainly still true that a man's dress hat should be an exact fit, the idea of fitted hats in the modern era refers more to the ever-popular baseball cap.
The Popularity of Fitted Hats
Up through the 1950s, the only wearers of baseball caps were baseball players on the diamond and young boys. And the boys wore the caps the way players would, with the brims facing forward. But with the passing of the Mad Men era and fedoras and bowlers being relegated predominately to dress hat category, rather than an integral part of a man's business suit, fitted baseball caps became something everyone wore to provide shade and indicate something the wearer supported. Initially, of course, the hats were always in support of a given baseball team. But as the hats became more trendy, they began to sport any variety of logos. You can get a hat featuring almost anything imaginable and suitable for any occasion.
Of course, the hats are usually worn with the brim facing backwards, so no one will know what you are supporting until you are walking away, but that might be considered half the fun.
Recently, more stylish hats are becoming popular among younger men - who also see them as better protection on a sunny day, but fitted hats are definitely not going anywhere soon.
What Makes Them Fitted?
While on a dress hat, it's the brim that is designed to fit a certain size head, caps are designated as fitted hats because you can custom fit them to your head. They have traditionally sported a set of straps at the back with studs and holes that allow you to tighten or loosen the cap as you like. This was a boon for manufacturers and customers alike, as it allowed the caps to be easily mass produced and cheaply sold. A company could make a child's hat and adult hat and then wearers could adjust - it's the very rare fitted hat that can't be made to fit. These days, many fitted hats have elastic at the back instead, but the idea is still the same.
Wearing Them Well
Men of any age can feel free to wear a fitted hat for most occasions and places except the obvious - evening and office. Many workplaces even allow them. While the trend is still towards wearing them backwards, anything goes. They can be worn with the brims facing sideways, or tipped up. Or even the old-fashioned way. Basically, whatever feels right to you on a given day is fair game.
Although the caps were designed to shade ballplayers' eyes, they are not actually the best option for protecting the face from the sun. That's not to say that you can't wear them as part of a summer ensemble, but you should definitely use plenty of sunscreen before putting on the hat.
One thing you probably already know is that fitted hats do give you pretty intense "hat head." Most men don't care, but if you happen to be going out later and won't have time to shower first, you should pack some hair gel.
Because the hats are inexpensive, it's easy to amass a large collection. Some vintage hats have become hugely desirable and can sell for a lot of money on eBay. You can buy fitted hats just about anywhere - either through the official site of the brand you're supporting or on any number of specialized web sites. Women may like to buy a lot of shoes, but for some men, it's all about the hats.