Hats at the Bar: Do’s and Don’ts

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Why are you, as a grown man, wearing a hat to the bar?

I wore a hat to the bar a few times like Freshman year of college when I was trying to go full Frat mode at a college that very much did not have fraternities, but that was it! I feel like people didn’t do it the rest of my time at school! Then I moved to Boston a few years after graduating and I go out on a Saturday night and every single dude on the dance floor looks like they copy and pasted this fit I just screenshotted off the ASOS website.

My question is WHY? Why wear a hat when you go out??? It doesn’t make sense to me! You’re getting “dressed up” like coordinating what you’re going to wear to go out for a night, a hat is just so unnecessary!

And look your first thought may be “maybe their hair’s thinning and they’re trying to hide it”. Here’s the thing:

1.If your hair is thinning you can only wear a hat if you have a girlfriend, you can’t be walking around hat-fishing girls. Gotta be straight up with it. They’re thinking you’ve got a McConaughey Mane underneath the Patagonia trucker just to find out you’ve got Larry David Locks. It’s false advertising and unethical.

2. 90% of the time the dudes wearing the hats have thick flowing hair I would kill for! And they cover it up under a $12 Bass Pro Shop hat that fits their head as well as a traffic cone!

This looks pisses me off so much.

And I’m also not one of those losers who’s like “why are you wearing a hat inside? There’s no sun, and you wear a hat to block the sun from your eyes so it doesn’t make sense”. Listen, no one has worn a hat to “block the sun out of their eyes” since the Industrial Revolution. We have a Lids in every shopping mall in America now. No one is wearing a customized Cookie Monster Fitted for the utility. I just feel like if you’re going out there’s no need to wear one!

Now if you absolutely feel the need to wear a hat to the bar, here are my guidelines to which hats are acceptable in which situations:

Cowboy Hat

A lot of New England guys love to pretend to be country guys by wearing jeans, boots, and a flannel but if you’re gonna dip your toes into the country world, don’t half-ass it, go all in. I’d respect someone who puts 10 gallons worth of southern charm on top of their dome over someone who cosplays Morgan Wallen by wearing a backwards trucker hat and saying the N-word when they think they’re not being recorded 10 out of 10 times.


If you’re rocking a ‘dora at the bar I am 1.) calling you Jason Mraz all night and 2.) expecting you to be able to scat on command. If you can do both of those things I think you’d look fedorable in this headwear.

Yankee Fitted

You better be ready to argue. I’ve never seen someone wearing this and having a good time. They’re always shouting “Do we got a problem?” at someone who doesn’t even realize they’re being talked to. If you’re wearing this you better be attempting to throw hands, and if you see someone wearing this, RUN.

Scally Cap

This can go either way. Either it’s the coolest dude you know: total townie, his whole family rocks these every day all day, Irish as hell OR, it’s the worst person you know looking for attention. There’s no in-between.


I get wearing this for the walk to a bar or something when it’s cold but the guy wearing this kind of beanie at a packed sports bar is always dripping in sweat, red in the face, and is way too prideful to admit he messed up by keeping it on. There is one exception though.

Carharrt Beanie

At least now I know who I can ask to bum a drunk cig off of.

Racoon Hat

Whenever you see guys wearing the ol’ raccoon pelt hat, make sure to verify where they were on January 6th, 2021. If they say the right answer, thank them for their service and say your lips are sealed if the FBI comes calling.

Nike Dry Fit

If you’re wearing this you better head to the bathroom and do some stretches, because I am 100% challenging you to a race outside. Winner keeps the cap.

Top Hat

There’s 3 types of guys who wear this hat and there’s different rules for each.

  1. If they have a long scraggly beard they are usually wise and honest, offer them some of the loose tobacco you carry around.
  2. If he’s wearing a 3 piece suit there’s probably a live rabbit underneath there. If you’re allergic do not accept his offer to “pick a card”.
  3. If they have a monocle they’ll probably try to buy Park Place from you in exchange for one of the RailRoad Stations but DON’T LISTEN TO HIM. He already has Boardwalk and if he gets both Blues it’s pretty much game over.

Visor with Hair

These are dangerous. Divorced dad’s will get this hat as a joke for Christmas but then they wear it out to the bar on the golf trip and after a few margaritas trick themselves into thinking it’s their real head of hair. A bald guy magically getting his hair back at the age of 62 will get a nuclear-level ego boost that could have family-ruining ramifications. My advice, don’t risk it.

Bedazzled Jean Hats

The 38 year-old bachelorette party has arrived and buddy, there’s a tornado of cocaine swirling towards the most disgusting bathroom stall you’ve ever seen in your life. These women will be slurring their words and trying to hook up with 22 year-olds by 10pm and honestly, I salute them. It is Karissa’s 3rd bachelorette party after all, why not let them get a little loose!

Propeller Hat

Guys wearing these at the bar are always like “Exsqueeze me sir? Could you pwease by me a beeya to dwink? I’m so firsty”. It’s like dude I don’t know you? And why are you holding a lollipop the size of a frisbee?


MFs at the bar wearing these are always trying to solve crimes and shit. Uhhh Sherlock, why don’t you solve the mystery of why you’ve got no bitches!

Subway Hat

LOL, dudes wearing these hats at the bar need to CHILL OUT. Always talking about “we don’t sell alcohol here sir this is a Subway” and “pull your pants up or we are going to call the police” like RE-LAX. We’re all out here trying to have a good time! Get a drink and stop being such a freaking narc!

So like I said, I’d say play it safe and just don’t wear a hat to the bar at all, but hopefully this guide let you know what can slide in the right places. And to those of you who attempt to rock one, I tip my cap to you (except the Subway hat guys you can all burn in hell for what you did to me).

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