Different Ways to Wear Hats for Long-Haired Guys

While we are all about equal representation for men and women, this article is written solely for the gents. Another time, ladies.

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), but 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 a challenge for long-haired fellas. Below is a list of things that you can wear and ways to go about it.

Ball Caps: This is a fairly standard piece of head décor, but it does require a little bit of 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 gives you the freedom to go about your busy day without your hair getting in your way, and you can 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 you’re wearing a ball cap. Gather your hair into a ponytail, but on your last pull through, only pull the hair halfway so that 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, but there are a few variations to add a little spice to your do. You can wear your ponytail down low so that it sits below the bottom of your cap, or you could wear it at the height of the cap’s opening so that you can 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 up 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 you can pull it through the opening in 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 still some different ways to add flair. For a little more control, tuck your hair back evenly behind your ears, or go au naturel by letting your hair hang in front of your ears.

Fedoras: One of the 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 do require you to do a little styling; otherwise, you will look unkempt. Pull some of your hair or bangs forward so that they frame your face, and try tipping the hat slightly upward to elongate your face and add some more interest.

Knit Beanies: These hats are great with long or curly hair, and they 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.

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 out several methods in a low-key environment. Make sure that your hat fits your head well and accentuates your face shape before you add it to your outfit rotation. A well-fitted hat can make all the difference.