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A Hat for Every Occasion

My wife tells me all the time that I have too many hats. She claims my closet looks like the clearance rack at Lids and frequently insists it’s time to thin the herd.  But here’s the thing, every hat has a purpose.  So instead of downsizing like a reasonable adult, I decided to double down and justify my collection.  Below is the core rotation I believe every person should have.  Not just hat-wearers. Not just men. Every. Person. If you’ve ever been told, “Do you really need another hat?” this one’s for you.

 

1. The Golf Hat

The quiet hero of every round.  I prefer something simple, structured and clean looking.  One day when my handicap dips below a 5, I’d love to mix in a tour visor or bucket as well.  


Eight golf caps are arranged on a striped surface. Colors vary: white, grey, blue, yellow, and black. Logos and text include Titleist and Cabot.

 

2. The Yard Work Hat

This is the get shit done hat.  It should be faded, frayed, sweat-stained, and shaped by years of grass cutting.  I regularly debate whether it’s time to retire these warriors, but they’re too perfectly worn-in to let go. Comfort beats appearances every time, especially when you’ve got mulch to spread.


Two navy yard work baseball caps on a striped surface. Left: NY logo. Right: Penn State, PlayStation Fiesta Bowl 2017 logo.

 

3. The Boating Hat

A proper boating hat needs one non-negotiable feature: an adjustable strap strong enough to survive a cross-bay gust. Ideally it’s made of a washable material too, because sooner or later it will take a swim. Salt water does strange things to a hat, so this one needs to be ready for battle.

 

Two boating caps on a striped surface: a white cap with "Montauk" text and a navy cap with an American flag. Neutral background.

4. The Workout Hat

Basically the yard work hat’s twin sibling. This is the one you can throw on for a jog or workout. Durable, unfussy, and impossible to ruin mostly because it already looks slightly ruined.


Two workout caps on a striped surface; one has a logo reading "Tremont, Est. 2020." The background is plain and beige.

 

5. The Hometown Hat

The great Eric Cantona said it best, “You can change your wife, your politics, your religion, but you can never change your favorite football team”.  I may not live in Pittsburgh anymore, but my teams are tattooed on my soul. There’s something special about wearing a hat that quietly lets the world know where you come from and who you’ll always root for.

 

Two Pittsburgh Pirates caps on a striped surface. Left cap is navy with a white "P," right cap is black with a yellow "P." Neutral setting.

6. The Gameday Hat

This hat gets more emotional mileage than any other in the lineup.  Still, I throw it on every gameday like a loyal fool ready to believe this is the year we break through and win the big one.


Two Penn State caps, one navy and one white, on a striped surface. Their brims have slight wear, conveying casual use.

 

7. The Winter Hat

Everyone needs a corduroy hat in the winter rotation. It pairs perfectly with flannels, jackets, and the general misery of Northeast winds. (Yes, beanies are great, but this list is strictly for brimmed hats. We’re operating under structure here.)

 

Navy Bunger Surfboards cap with red trim features an oval badge reading "Custom Surfboards by Bunger, Babylon, New York" on a striped background.

8. The Bar Hat

This is the category most of my hats start in.  The clean, presentable ones that haven’t yet been sweat-stained into another life. Perfect for breweries, casual hangs, and pretending I’m stylish when I really just put on the first decent hat I saw.


Three baseball caps on a striped surface: left navy with Kismet Inn text, middle black with BWI logo, right navy with a large "B".

 

9. The Obligatory Golf Tournament Hat

Every golfer knows this hat and probably regrets buying at least half of them.  You swear you won’t fall for it again, and yet there you are, walking out of the pro shop with a fresh, overpriced embroidered souvenir you absolutely did not need. It’s tradition at this point.


Three beige caps on a striped surface. Left cap has a green anchor, middle has "ryder cup bethpage black 25," right says "125th U.S. Open Oakmont."

 

10. The EPL Hat

“Of all the unimportant things in life, football is the most important”.  If you don’t already follow the English Premier League (EPL), I highly recommend you start.  Glory Glory Man United.


Gray baseball cap with Manchester United logo in red and yellow on the front, resting on a striped fabric background.

 

 
 
 
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