Most stylish men secretly wish they’d been born in an era when hats were standard attire. If you’ve never donned a proper hat like a fedora or pork pie hat we can tell you that the feeling it bestows is similar to wearing a tuxedo or a military dress uniform. You simply feel more masculine.
Although the days when all men wore hats are not likely to return, it’s all the better for daring types who relish the opportunity to showcase a little individuality.
So, if you’ve ever been tempted to bust out a hat but are concerned that it might be too ostentatious, here are a few tips on how to put one on — and pull it off.
The easiest hat to wear (besides the baseball cap variety) is a tweed newsboy cap. Because they’re less formal, they’ve managed to remain more common and will not convey an overly retro vibe. Wool for fall and winter, linen or cotton for spring or summer, they’re super versatile and pair with a polo shirt or sweater just as well as with a jacket and tie.
For proper hats like panamas and fedoras, it helps to remember that every feature of men’s clothing was developed for a utilitarian purpose (like bellowed pockets on tweed hunting jackets, which made it easier to carry shotgun shells). So with hats, start by realizing that their primary function is to protect the head from the elements. Wearing a fedora in the wind, cold, and falling snowflakes will greatly reduce any self-consciousness you might feel, since your hat is actually serving its purpose. Ditto for donning a panama, which makes perfect sense if you’re in the sun all day.
Finally a word on hat etiquette. Tipping your brim at every passing lady would be anachronism overload. As for removing it indoors, this only applies to intimate environments like someone’s home, or a meeting in a private office. You don’t need to remove your hat in the lobby of a theater, though you probably should when you take your seat. The folks behind will thank you.