The Best Hats and Styles for Guys With Medium-Length Hair

Co-authored by Tami Claytor and Hunter Rising

Last Updated: July 31, 2022 References

Have you grown your hair out and want to look fashionable when you put on a hat? Medium-length hair has a little extra volume to work with, but you can still easily rock a ton of hats without ruining your 'do. Keep reading for recommendations of hats you should try and ways to protect your style when you're wearing them!

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Best Hats and Hairstyles for Medium-Length Hair

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Baseball cap Rocking a baseball cap is a classic look for keeping the sun out of your eyes and your hair under control. Since the cap has an adjustable strap, you can easily loosen it up so it doesn’t squeeze the sides of your head and ruin your hairstyle.
- Slick your hair back and put on your cap. Then, tuck any hair on the side of your face behind your ears for a loose, relaxed style.
- Tie your hair up into a ponytail and pull it through the hole above the strap to keep it out of the way.^{[1]
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- Try putting your hair in a top knot before wearing your cap. Then, just tuck any stray hairs on the side of your face into the cap.^{[2]
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- Tilt the brim of your cap up and let your bangs hang down for a really casual look.
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Newsboy cap A newsboy cap has a short brim and loose, rounded top that gives voluminous hair a little more room. You can rock a newsboy cap with any casual style or when you want to get a little dressed up. Just keep the brim angled slightly upward so the cap doesn’t fit so tightly around your head.
- Let your hair hang down naturally to help frame your face.
- Try slicking your hair straight back before putting your cap on if you want a cleaner style.
- You can pull your hair into a low ponytail so it sticks out below the bottom of the cap.
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Bucket hat If you want to sport a casual look that’s right out of the 90s, a bucket hat is the perfect choice for you. Bucket hats have a roomy top and loose fit around your head so they’ll work well no matter how long your hair is. Just make sure you don’t pull the hat down too far on your head, or else it could flatten a fuller hairstyle.
- Slick your hair back and tuck it behind your ears before putting on your hat to keep it out of your face.
- Part your hair down the middle or to one side, and let it hang down on the sides of your face for a casual style.
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Knit hat Knit caps and beanies are really versatile and the perfect addition to your outfit when you want to stay warm.^{[3]
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Research source} You can rock a knit cap with pretty much any style and hair length, but try finding one made with cotton or fleece since the fabric is more breathable.^{[4]
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- Push your hair back so it’s out of your face and slide on your knit cap to keep your hair under control.
- Tuck your hair behind your ears and wear a knit cap a little higher on your head so your hair hangs out from the back.^{[5]
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- Let your bangs hang down on the side of your face and put your cap on for a really casual, relaxed look.
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Fedora When you need a hat for a formal occasion, a fedora is a great option. The fedora’s brim helps frame your face and gives you a striking look. Since the hat sits loosely on top of your head, it won’t flatten or crease your locks.^{[6]
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- Comb your hair back and put on your fedora. Push any loose hair on the side of your head behind your ears to have a clean look.
- Let your hair fall naturally around your head when you wear a fedora, but be careful not to pull your hat too far down on your head or it will make your hair puff out above your ears.
- You can comb your hair back and pull it into a ponytail before putting on your fedora.
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Trilby A trilby looks really similar to a fedora, but it has a smaller brim that’s angled downward. Since you usually tilt a trilby back when you wear it, it shows off any bangs or fringe you have near the crown of your head without ruining your style.
- Let your bangs or fringe hang down so they frame your face and give you a clean, stylish appearance.
- If you want a slicker look, comb your hair back and put on your hat. Then, tuck any hair on the sides of your head behind your ears.
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Sun hat Sun hats have really wide brims to keep the sun out of your eyes on a bright summer day. Since sun hats are made from lightweight and breathable materials, you’re less likely to sweat and ruin your hairstyle when you’re going on a casual summer outing.
- Let your hair hang down naturally for a relaxed summer look.
- If you want to rock a flow style, slick your hair back before putting your hat on and tuck it behind your ears. Let the hair on the back of your head hang out from the bottom of the hat.
- Sun hats also work well if you want to tie your hair into a low ponytail or man bun.
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Cowboy hat A cowboy hat has a tall crown that leaves a lot of room for a full, voluminous hairstyle underneath. Cowboy hats are best for casual styles when you’re outdoors since they’re lightweight and have a wide brim that keeps the sun out of your eyes.
- Comb your hair along its natural part and let it hang on the side of your face. Just set the hat lightly on top of your head without pushing it down so you don’t crease your hair.
- Push your hair back and put on your cowboy hat. If you don’t like how your hair hangs down, just gently tuck it underneath the brim with your fingers.
- Put your hair into a low ponytail at the back of your head before putting on a cowboy hat if you want to keep your hair under control.

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Tips to Avoid Hat Hair

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Shampoo and condition your hair. Hats can make your hair a little staticky, but shampoo and conditioner add moisture so your style holds better. When you shower, gently lather your shampoo into your hair and follow up with some hydrating conditioner to seal in the moisture.^{[7]
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- Washing your hair every day can dry out faster and make it difficult to hold a style. Only wash your hair every few days or when it’s noticeably dirty.
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Apply an anti-frizz spray to your hair to tame flyaways. If you have longer curly or wavy hair, a hat could make your locks look frizzy. When your hair is damp, spritz your anti-frizz spray onto your hair and comb it through with your fingers so your style stays clean and professional under your cap.^{[8]
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- You can instead use a sea salt spray to help your hair hold your style underneath your hat.
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Dry your hair completely before putting on a hat. If you put on your hat while your hair is still wet, your locks will conform to the shape of the hat and flatten your style.^{[9]
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Research source} Gently pat your hair dry with a towel or use a hairdryer on a low setting until your hair feels dry to the touch.
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Choose a hat that fits a little looser on your head. Hats that are too tight leave creases in your hair and could push down any style that you try wearing. When you put on a hat, try putting one finger between your head and the brim. If you can’t easily fit a finger in between, then your hat is too tight.^{[10]
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- Hats that are extremely tight can also pull out loose or damaged hairs when you put them on or take them off.^{[11]
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Rub water or gel through your hair to restyle it. If you plan on taking your hat off, you may need to lightly fix any hat hair that it left behind. Wet your fingers with some water or take a dab of water-soluble gel and comb through your hair with your fingers to reshape your locks back into the style you want.^{[12]
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- Avoid using a brush to fix your hair since you could make your locks look more frizzy.
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Try dry shampoo if you need to revive your hair’s volume. If you want a full hairstyle after you take a hat off, spritz some dry shampoo into your hand and finger-comb it through your hair. The dry shampoo will absorb any sweat or oils in your hair so you’re able to style your hair when you need a quick fix.^{[13]
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- You can use dry shampoo on days when you don’t wash your hair in the shower to help style it.
- It is good etiquette to take your hat off when you are inside or in the presence of a lady or someone in authority.^{[14]
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- If there is no hat rack, you can put it on your knee.
- Or put it on the back of your chair.