Menswear seems simple in the way that math seems simple. You can get by just sticking to the basic equations. But if you add one wrong number—like transition lenses or weirdly baggy khakis—your formula will fail.
The dumb hat I’m referring to is something of a glorified fedora with a wider, flatter brim. It's the one you see most often in Los Angeles, among the type of guy who also carries around a motorcycle helmet with no motorcycle in sight. It's the one many men may turn to when they are newly divorced and ready to invest in a new, badder identity alongside an overpriced leather jacket. It’s been described as a pilgrim hat, but for pilgrims who drink craft IPAs and live in Williamsburg. There is no casual way to wear this hat. You commit to the role of Hat Guy the minute you put it on your head. And don’t even think about taking it off. Where will you put it? People don’t have hat racks anymore! “I’m wearing an accessory!” the hat screams.
The saving grace for hats like baseball caps and beanies is their modesty and functionality. Pilgrim hats provide neither warmth nor shade. You can’t wear one casually. The hat commands attention and lets everyone know that you’re trying to pull a look. It’s for this reason that wearing it comes with such bravado and vulnerability. A hat man is attention-seeking, yet self-conscious. He takes himself seriously enough to think he is someone who should be wearing something on his head.