It’s relatively easy to pull off a fashionable look in the fall and winter. All you really need to do is go rugged. Wear some leather boots (no square toes, though!), dark jeans, a plaid shirt and a dark jacket. With almost no effort, you look like a manly man.
It’s a bit tougher to pull off a solid look in the spring and summer. If you go with colored shorts and a tank top, you look like a preppy bro. Cargo shorts and a graphic tee? Stoner. Khaki shorts and a striped polo? Corporate intern.
Throw hats into the mix and things become very, very complicated. Hats aren’t just an accessory you can add to any outfit, like a watch or a bracelet. Hats become the focal point of what you’re wearing. They’re difficult to pull off for those of us who aren’t GQ models.
Few guys realize this, however. Take a walk on a sunny day and you’ll see all kinds of hat-sporting dudes committing crimes against fashion. Most have no idea how ridiculous they look. My goal is to change that.
For starters, I’m going to assume that all guys have enough sense to know that cowboy hats, top hats, pope hats, berets and all the other crazy hats men have worn throughout history are never acceptable (unless, of course, you’re a real cowboy, Abraham Lincoln or the Pope).
Instead, I’ll focus on three hats I see guys wearing all the time — to my intense dismay. These are hats that a lot of guys mistakenly believe are acceptable and even fashionable. I assure you, they are not.
Then, I’ll recommend the one hat that every guy can actually wear without looking like a douchebag. This doesn’t necessarily mean that you should wear it (generally, no hat > hat), but it’s the best choice for when you absolutely have to put something on your noggin.
1. Never wear: fedoras
The first rule of wearing hats is you never wear a fedora.
The second rule of wearing hats is you never wear a fedora.
Got it? You sure?
Until you figure out how to time travel back to the 1940s and become a top detective in Hollywood’s seedy underground, it will never be acceptable for you (or anyone else) to wear a fedora.
There are still far too many guys — usually the type who build custom PCs and don’t realize that hair grows on the neck as well as the face — who think fedoras are a quick and easy way to look suave and sophisticated. On the contrary, they make you look like a total tool who’s trying way too hard.
Exhibit A, which should be the only exhibit you ever need:
Need just a smidge more convincing? Try to make it at least a minute into the tidal wave of cringe that is this video. You’ll never touch another fedora:
Note: Panama hats, the straw cousin of fedoras, fall under this umbrella, too.
2. Never wear: newsboy caps
Got a mirror nearby? Even a phone with a front-facing camera will do.
Take a look at yourself. Check out your complexion and hair. Stare deep into your own eyes.
Are you Samuel L. Jackson?
Then you don’t get to wear newsboy caps. Sorry, that’s just how it works. It doesn’t matter if you wear them forwards or backwards. It doesn’t matter if they’re black leather, gray knit or whatever the hell this is. It’s a firm no however you slice it.
3. Never wear: bucket hats
The era of the bucket hat has passed. They were actually pretty awesome back when hip hop was a new and cool genre of music, but at this point it’s pretty much down to L.L. Cool J and dads on vacation. Don’t align yourself with that crew.
Exception: outdoor music festivals. Sometimes, fashion gets trumped by not-getting-skin-cancer. Large bucket hats — even ones with that awful string that hangs down below your neck — can be a necessity for fair-skinned music fans spending the day at Coachella, Bonnaroo, etc. Do your best to stick to neutral colors, but don’t worry too much about how your hat looks; everyone around you is way high on drugs and probably thinks you’re a dragon.
4. Never wear: beanies
It’s the summer. The top of your head is plenty warm. Take that beanie off, you idiot.
Okay to wear: plain baseball caps
Sometimes, wearing a hat is essential. The sun is a bright motherf*cker and you can’t have it blasting you in the face all day. For these occasions, wearing a baseball cap is acceptable.
Generally, your best bet is to go with a plain, dark, fitted ballcap. Something like that one over there on the right.
Five-panel hats are a slightly trendier and more fashionable option, but they don’t work too well unless the rest of your fashion game is on point.
Authentic New Era 59FIFTY baseball caps (i.e. the hats worn by Major League Baseball teams) are okay as a last resort. Teams with dark-colored hats with matching brims and plain logos are your best options — New York, Boston, Detroit, San Francisco, etc.
Stick to fitted caps (no snapbacks unless you’re still in high school) and never deviate from official team colors — no camouflage or Scumbag Steve-esque patterns!
Also, take the damn stickers off.