So unless you live in Japan, London or Brooklyn, you’ve probably seen your fair share of crimes against humanity when it comes to head dressing. Hats can be a lovely accessory for the refined man–an extra little touch of fashionable detail to complete that look you’re going for. There’s no question that the whole dandy/throwback gentleman’s look is in. Looking like you’ve stepped out of a time machine straight from the ’20s or ’40s can certainly be an accomplishment worth striving for. And yes, in those cases, a hat to finish off your look is a must. But let’s be honest, boys, there’s probably a few hats kicking around in your closet that you’re a little too fond of. Here, I will break down for you a few different categorizations and discuss their potential…

Let me be straight up with you: I don’t like most hats. In fact, a cruise around The Sartorialist actually makes me not mind hats to complete a look, but confirms my suspicions: the men who pull off a strange hat have got it GOING ON. Usually, they’re topping off a fine, expensive suit with a bowler hat or a pork pie hat (yes, there’s a difference), and it works. But that’s because they’re styled to the nines and wearing a 300-dollar hat. You in your Old Navy jeans, ribbed sweater, and engineer cap at the bar on a Friday night? NOT WORKING. Please take heed.

The conundrum of a stylish man, no? There is something charming and boyish about a ball cap pulled off well. Certainly there’ve been a few designer riffs on the New Era lid. And if it’s shaped well, is clean, and goes with an outfit you’re putting together (let’s say urban casual sportswear), then do it up. Imagine an un-shaped brim with a hoodie, high tops and slouchy jeans. Absolutely! The hat you wore playing baseball in high school? The sun-faded cap you played college softball in? Leave ‘em at home and run a damn brush through your hair.

The answer is no. Remember how Ashton Kutcher and Von Dutch made these damn things ubiquitous? Please, let’s never go there again. Unless you are Justin Timberlake, throw that hat in the garbage and don’t look back.

Let’s be clear about this one: these are seasonal hats. They are only to be worn in the fall or winter. They can be attractive on a certain man and obviously functional. For men with longer hair, this is often their best option for controlling a dirty, disgusting mop. But greasy hair peeking out from under your beanie, with a plaid flannel button-down and skin-tight jeans, is the easiest way to look like a cliché. Take them off when you go indoors and don’t wear them bunched up on the top of your head–pull them down to your ears. Also, stick with solids and non-abrasive patterns (please no teams or brand logos).

This one causes riffs. They’re everywhere. Now that they’re affordable and in every department store, men across the country think they can be stylish and avant-garde in them. Truth is, most men look like tools in a fedora. Al Capone, Indiana Jones, and Freddy Krueger look awesome in them. Seems like the simple truth to me: they’re for girls to look cute and edgy in, and for men to look like asses in (unless you’re wearing a three-piece suit or performing at the VMAs and need a hat to throw across the stage).

The hat that Chaplin and Magritte made famous has a lot more wriggle room, in my opinion. These hats are of the moment and of the future. See, there’s no essence of swagger here. It’s all stodgy, stuffy nerdiness. These hats cannot be cocked to the side, they can’t be recreated with crappy houndstooths, and they can’t be worn to ‘the club’ with shredded jeans. They’re for a distinguished man with an umbrella, a suitcase, and an important place to be. However, they really only work for special occasions—i.e., not to be worn to the grocery store or out to dinner (pssst: pork pie hats have flat tops).

This one’s gonna hurt. There are A LOT of men out there trying desperately to seem cool and distinguished in these hats. Sure, you’ve seen Brad Pitt look devastatingly handsome in one, but what DOESN’T he look devastatingly handsome in? Newsflash: You’re not Brad Pitt. If you’re going to wear one, make sure it’s tweed and wear it with a blazer and either dark jeans or corduroys. Or maybe a v-neck sweater over a button-down that’s carefully sloppy.

Last winter, everyone had to have a fur-lined hood on their massive winter jacket. If not fur-lined it was fur-trimmed; just enough to prevent all conversation from getting to your ears, and enough to make you dip your head back so you can see what’s in front of you. Yeah, let’s not do that again this winter. If you want that stylish fur-trimmed winter look, get a handsome bomber hat. They’re functional, they’re a little dramatic, and they make you look like you know what’s going on (fashion-wise, at least).

This hat, along with trucker hats, needs to be retired from wardrobes for good. I don’t care who made it (Kangol, Polo, Gucci, GAP), it NEVER looks good. Vacation? Nope. Golfing? Get a visor if you must. The beach? Find a giant, floppy, straw hat instead. River rafting? Do you really need to wear a hat that badly? Don’t let anyone tell you differently: this hat looks stupid on you.



  1. hearthesiren

    ooooh, love this post!

  2. mitchellryan

    lay down the law once again, bill.

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