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8 Cool Hat Ideas for Guys with Medium Hair

Most men struggle when trying to figure out how to wear a hat with medium hair. Some choose the wrong type of hat for their overall style, and others hide all of their hair under it and end up looking lackluster.

But there is a way for you to look your very best, show off your medium-length hair and wear a stylish hat that matches your outfit and the vibe you’re going for. It just takes some experimentation to find what works best, and looking for inspiration doesn’t hurt.

Cool Ways To Wear A Hat With Medium Hair for Men

Are you ready for some medium hairstyles with hats you’ll just love? Check out the pictures below.

1. Easygoing Trilby Hat

trilby hat for men with medium hair

Guys with medium hair wanting to create a fun and carefree vibe should opt for a trilby hat. It often looks great on mature men.

Light colors pair well with dark grey hair. Part your hair close to the middle and style it in front of your ears, so it’s visible.

2. Baseball Cap on Gray Hair

baseball cap for men with medium hair

When learning how to wear a hat with medium hair, guys often think of the baseball cap.

It’s classic for all ages. Brush your hair back so most of it is visible at the sides and back of your head. Opt for a simple style, so the cap doesn’t mess it up.

Related: Hat Size Chart

3. Jaunty Bowler Hat

bowler hat for men with medium hair

When wearing a gentlemanly bowler hat, the front of your hair will be covered, so the back better look good. Manly layered hairstyles with a little texture work best.

4. Cowboy Hat

cowboy hat for men with medium hair

Cowboy hats give off a very particular vibe. However, getting a hat similar to a cowboy one but with a shorter brim can sit neatly on top of thick, textured hair and work with any aesthetic.

Wear a light-colored hat with dark tresses and accessorize with sunglasses.

5. Classic Beanie

knit cap for men with medium hair

You can’t go wrong with a knit cap, also called a beanie. It works for bad hair days, but you can also wear one when your tresses look their best.

You need bangs, and preferably side bangs, falling across your forehead. Make sure there’s a little volume at the front of your hair, too.

6. Newsboy Cap on Layered Bob

newsboy cap for men with medium hair

It takes a particular type of person to pull off a newsboy cap. Pair light color with light hair, wearing it slightly to the side.

It’s best for accessorizing medium hair on the longer side. Layered hair framing your face will look really good with it.

7. Dark Hat + Salt and Pepper Hair

medium hairstyle with hat for asian men

Guys, wearing a dark hat with a bright ribbon help when you want to draw positive attention to your medium hair.

Have your salt and pepper hair around chin length and brushed back behind your ears to look beat underneath your head accessory. If you’re into long hairstyles, try these hats with your long hair.

8. Wide Brim Hat with Dreads

medium dreads with hat for men

A wide-brim hat worn around the crown of your head can frame your hairstyle and face nicely. Pink is a bold choice for men who want the freedom to explore their style.

Pairing medium dreads with a hat can keep you looking incredibly trendy, especially if the accessory’s color contrasts door locks.

If you’re a guy with medium hair, all types of hats won’t suit you. Knowing what hat to wear with your medium hair can give you a bolder look!

Try different colors and styles, and know what hats work best for your haircut. You have the perfect hair length to show off your style wearing a hat.

Hair that falls around the face works best when accessorizing with a hat. However, some hat styles also work best for showing off the front or back of your locks. Change it up day by day to highlight different aspects of your look.

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