10 Cool Hats for Men

A cool hat should make people think that you have your life together. It should complete your outfit—like a missing puzzle piece.

It should make people think that you chose it because it was the proverbial ‘cherry on top’ of your fit instead of hiding the fact that you didn’t have time to do your hair today.

I’ll be looking at cool hats for men for all seasons, in all styles (besides the uncool ones), and telling you how you can decipher which hat should sit atop your head like a king’s crown.

What Makes A Cool Hat For Men? 

People have seen enough fedoras and bowler hats to know that those aren’t typically considered cool hats for men. What makes them uncool? What do they lack that other styles possess?

It comes down to formality. Hats shouldn’t be the focal point of your outfit. They’re an accessory at best, meaning that you’ll want them to be as lowkey as possible. The best hats are both casual and functional. 

Sadly, bowlers and fedoras don’t do much these days besides tell people that your personality is older than your body.

Finding The Coolest Hats For Men 

Cool hats for men should have a central function. They should either keep you warm, keep the sun out of your eyes, or help you hide your haircut. How they go about accomplishing that goal is what makes them cool.

Technically, a cowboy hat could do those tasks just as well, but there’s a reason why you don’t see as many cowboy hats as you do beanies.

A cool hat should look effortless and like it belongs on your head—instead of making you stand out like Indiana Jones in the middle of a space rave.

The 10 Coolest Hats for Men 

Here’s my list of the coolest hats for men. I’ve included these items based on their style, their price, their construction, their durability in bad weather, and their purpose. 

1: Easy Box Snapback Hat

The Easy Box Snapback Hat uses raised embroidery to add subtle texture to our simple boxed logo. This classic 5-panel hat also includes an adjustable snap at the back for quick customization, and is made with 100% cotton.

Price: $26.00

2: Tommy Hilfiger Logo Baseball Cap

Tommy Hilfiger men’s hat. Top off your look with our premium cotton cap made complete with our signature branding.

  • 100% cotton.
  • Custom embroidery, adjustable strap.
  • Imported.

Price: $19.50

3: Short Beanie With Seams

Short beanie with a turn-up brim and adjustable back.

Price: $12.20

4: Elijah Berle Snapback Hat

Stylish, effortless, classic, dependable, and built for the job of skateboarding—and the footwear and apparel aren’t bad either.

We partnered with Elijah Berle to build a collection of Skate Classics and apparel that speaks to his passion for classic tattoo art, motorcycle culture, retro surf, and mid-century fashion.

With embellishments ranging from embroideries and outsole prints to detachable patches, this head-to-toe collection pays homage to Elijah’s elevated taste level and iconic style.

Featuring embroidered artwork at the front, the Elijah Berle Snapback uses a 5-panel cotton construction with a green undervisor and checkerboard Vans flag to create a modern hat with a unique old school vibe

Price: $28.00

5: Colour Block Bucket Hat

Wide brim hat with topstitching detail.

Price: $15.90

6: Pop Drop Bucket Hat

Tommy Hilfiger unisex hat. This bucket hat adds throwback flair to anything you pair it with. Introducing Tommy Jeans Pop Drop: easy Tommy pieces, colored outside of the lines. Dance off-beat in these head-turning styles made with bold logos and eye-popping color. A limited-edition style from our Tommy Jeans collection.

  • 100% polyester.
  • Imported.

Price: $39.90

7: Salton Hat

Giving a nod to 90s nostalgia with classic skateboard embroidery at the front panel, the Salton Hat brings an instantly upgraded look to a timeless style. This 6-panel retrofit jockey hat is made with 100% cotton and features an adjustable back.

Price: $28.00

8: Tropical Print Bucket Hat

Tommy Hilfiger men’s hat. Inject a dash of throwback style into your wardrobe courtesy of our tropical print bucket hat.

  • 100% cotton.
  • Imported.
  • One or more style images shown is a 3D image. The actual product may contain subtle variations.

Price: $34.50

9: TJ Mesh Cap

Tommy Hilfiger men’s hat. Keep the rays (and the heat) at bay in our logo cap featuring mesh side panels that make for a lightweight, airy lid. Made from recycled nylon, for a kinder impact on the planet. Part of our Tommy Jeans collection.

  • 100% recycled nylon.
  • Imported.

Price: $39.50

10: Howell Shallow Unstructured Hat

Featuring rose embroidery inspired by classic tattoo art, the Howell Shallow Unstructured Hat brings bold Vans style to an old school cap. Made with 100% cotton, this 5-panel unstructured hat also includes an adjustable back closure to ensure a comfortable fit.

Price: $28.00

What Are The Most Popular Cool Hats For Men?

There are no particular hats that are the most popular. Instead, certain styles seem to stand out from the crowd.

The coolest hats for men fit into a few categories, but commonly you see people wearing dad hats like the Tommy Hilfiger Men’s Logo Dad Baseball Cap, snapbacks like the Vans Easy Box Snapback Hat, or beanies like the Zara Short Hat.

What Styles Of Cool Hats For Men Can You Get?

Hats come in all different styles, but not all of those styles are necessarily chic. When looking at cool hats for men you’ll find that the majority lean towards modern trends. Nowadays, the most popular styles are beanies, dad hats, baseball caps, and fitted hats.

There are other styles that aren’t as versatile but are nevertheless cool. These include safari hats and bucket hats. They’re trickier to pull off but if you can then you’ll be raking in compliments from those who appreciate good fashion.

How To Style Cool Hats For Men

I came up with our first styling tip by considering how to navigate a precarious scenario—how do you make a bucket hat look good? To answer this question, I suggest keeping your outfit as basic as possible.

Pick clothes that fit your body, select neutral colors, and wear subtle shoes. That way your bucket hat can speak for itself

You can also coordinate your hat with the rest of your outfit. This works well with minimalist beanies.

Since they usually don’t have patterns, it’s as simple as pairing them with the rest of the colors in your ensemble. That way you’ll put together a cohesive, harmonious outfit. 

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