The newsboy cap and other stylish hats

As guys, we like wearing hats. Maybe it’s because most of us are going bald, and the ones who aren’t going bald never comb their hair. So if you’re going to give up on your hair for the day, or for the rest of your life, then you should at least do it with style, and not with a baseball cap, which is only about two notches above sports jerseys on the style meter.


The foundation of any stylish hat collection is the newsboy cap. It works because almost no other article of clothing spans all the echelons of society. Everyone from the hedge fund golfer to the, um, newsboy can get away with a newsboy cap. Some people will say that you need to be old enough to grow a full mustache before you can wear a newsboy cap, but this is just people’s 21st Century bias talking.
Often confused with the newsboy cap, the flat cap is the European version of the newsboy cap with more of a working class feel to it. But like all things working class, members of the upper strata of society have adopted the flat cap to seem more egalitarian. It’s like how Americans with jobs sometimes pretend to like Bruce Springsteen.
In addition to the newsboy cap and flat cap, we have the option to wear berets or fedoras. While these two hats are indeed trendy, they are far from stylish. Unless you want people to stereotype you as an ineffectual poet, so if you have to wear a hat at all, I’d stick with the newsboys and flats.