Different Ways to Wear Hats for Long-Haired Guys

Hats off to all the long-haired gentlemen out there! Are you searching for the perfect way to top off your flowing locks while showcasing your unique style? Look no further! 

In this article, we’ll explore a variety of hat styles and techniques tailored specifically for you, the long-haired guy. From classic fedoras to trendy beanies, we’ve got you covered – literally. 

So, grab your favorite hat and prepare to be inspired as we delve into the world of versatile headwear options that will not only protect your tresses but elevate your style game. 

But let’s kick things off with a walk down memory lane.

The History of Long Locks

Women have been rocking the long hair/hat combo for hundreds of years (try Googling “medieval women’s hats” for some stunning examples). Actually, we have an interesting article on stylish ways women wear baseball caps.

Still, men’s fashion has never been quite as consistently accepting of cascading tresses. From the Egyptians through Rome’s heyday, men’s hair was either shaved or cut relatively close to the head, with Julius Caesar’s hairdo as a prime example. 

However, as Europe mixed with the Germanic people after the fall of the Roman Empire, the men started wearing their hair longer than they had in the past. Still, lower to middle-class men kept their hair short or shaved for hygiene and status reasons.

The exception to this rule is where the wealthy were concerned. Long hair on men has typically been a symbol of status and riches, and if they couldn’t grow it themselves, they would wear styled wigs. Long sideburns often supplemented the luscious locks and the comb-over even became popular for a brief period of time, though it’s generally considered a fashion faux pas nowadays (sorry, Mr. President). Men’s long hair started to take off again with the rise of the rock and roll era. The Beatles, Elvis Presley, Bob Marley, and Kurt Cobain are still influencing the men’s hair scene with their mop-top, pompadour, dreadlocks, and long hair, respectively.

What to Wear

It’s all fine and dandy to know that lengthy locks have been fashionable throughout the ages, but finding the right headgear can be challenging for long-haired fellas. Below is a list of things you can wear and ways to go about it.

1. Ball Caps

This is a fairly standard piece of head décor, but it requires a little styling to make it look good with long hair.

The Hidden Gem

If your hair is short enough and you need to keep it out of your face, consider stuffing it completely under your ball cap. This allows you to go about your busy day without your hat hair getting in the way. In addition, it lets you relive your short hair days without actually getting a cut.

The Low Tuck

Whether worn down the center or pulled to the left or right for a little more interest, the low tuck is a good way to go when wearing a ball cap. 

Gather your hair into a ponytail, but on your last pull-through, only pull it halfway so it tucks underneath. This will keep your hair under control when you’re out and about on a windy day.

The Double Vision

Channel your inner Willie Nelson with this hat and long hair combo. Once your ball cap is on your head, divide the remaining hair into two sections and use an elastic on either side to hold each tail in place. Switch things up by wearing the elastic low or high or placing both ponytails in front of your shoulders or behind.

The Pony

This look is a classic when you have long hair with a ball cap. Still, there are a few variations to add a little spice to your do. 

You can wear your ponytail down low so it sits below the bottom of your cap, or you could wear it at the height of the cap’s opening to draw it through. If you want an even fuller look, skip the elastic altogether and just pull your locks through the back opening for a more laid-back look.

The Bun

Whether drawn back tightly into a bun or gathered into the “messy bun” style, this hairstyle with your ball cap is a surefire win. You can either wear your bun down below your hat or pull it through the opening in the back to add a little bit of variety.

The Flow

Let it all hang loose! You don’t have to tie back your hair at all with this look, but there are different ways to add flair. For more control, tuck your hair back evenly behind your ears, or go au naturel by letting your hair hang in front of your ears.

2. Fedoras

One of Fedora’s biggest perks is that it can add a little bit of class to your wardrobe without taking too much time to style your hair. 

Fedoras can dress up just about any outfit, but they require a little styling; otherwise, you will look unkempt. 

Pull some of your hair or bangs forward to frame your face, and try tipping the hat slightly upward to elongate your face and add some more interest. These hats are so versatile; they even look great on women.

3. Knit Beanies

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These hats are great with long or curly hair and provide the additional benefit of substantial warmth. Try to avoid overly baggy beanies, though, as they can detract from the overall look you may be going for. 

Check out this guide to custom beanie hats for more on this incredible type of hat.

4. Baseball Caps

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Baseball caps are timeless, incredibly versatile, and won’t ever go out of style. If you have long hair, you can wear them in two ways: with bubble ponytails for long straight hair. 

Try wearing your baseball cap backward when you let your hair down. It’ll give you a cool-as-a-cucumber casual look. Otherwise, stick your ponytail through the opening in the back when you wear it in the traditional way.

5. Beret Hat

The beret isn’t exactly the first hat that comes to mind when looking for something that gives off a masculine vibe, but that’s okay. This hat is the perfect match for guys with long locks and softer features. 

That said, they’re versatile enough to go with most facial types, hairstyles, and clothing that fits the wearer’s personal preference.

6. Panama Hat

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Although it excels at adorning short straight hair, the Panama hat can work well with a regular braid (provided you pull it back). This hat can bring a touch of style and elegance to most casual and formal outfits alike.

7. Summer Hat

Summer hats pair well with various hairstyles (especially when covering up a bad hair day). However, they’re especially useful for protecting your textural hair from sun exposure. 

Beat the heat while complementing a casual outfit with one of these bad boys for a laid-back summertime look.

8. Bucket Hat

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A bucket hat works best for people with medium hair, especially hair with natural curls. Bucket styles are ultra-laid-back, though, so they work best with clothing that gives off a casual appearance. Leave them at home when attending formal events.

Speaking of which, you can check out our guide on hat-wearing dos and don’ts for more tips on how to avoid breaking hat etiquette.

9. Boater Hat

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What do you get when you pair medium hair with a short casual ponytail and a boater hat? An interesting style statement from a bygone era, that’s what. 

These hats have an unmistakable summer feel to them and will give your Bohemian-style outfit that extra touch of class.

In Closing

Hats and long hair can work together seamlessly if you know what you’re doing. The best way to move forward with this look is to try several methods in a low-key environment. Make sure your hat fits your head well and accentuates your face shape before adding it to your outfit rotation. A well-fitted hat can make all the difference.