How to Wear a Hat with Medium Hair Guys

by  Mila M.Cosmetologist

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Choosing the right hat for your medium length hair can seem like a daunting task. With so many styles to choose from, it’s important to find one that complements your hairstyle and face shape perfectly.

This guide will walk you through 11 great hat styles for men with medium length hair, along with tips and tricks on how to wear them stylishly. Let’s dive into the world of hats!

Key Takeaways

  • Choose a hat that is comfortable and complements your medium – length hair.
  • Experiment with different hat styles to find the one that suits you best.
  • Tuck or tie up longer hair before wearing a hat to prevent it from getting tangled.
  • Don’t be afraid to let your hair down and embrace its natural texture while wearing a hat.

Choosing the Right Hat for Medium Length Hair

When choosing a hat for your medium length hair, it’s important to consider both comfort and how well it complements your hairstyle.

Consider comfort

Opting for a comfortable hat is as important as choosing one that complements your medium-length hair. Comfort revolves around the right fit, which neither squashes your head nor sits too loose.

A well-fitting hat lets you go about your day with ease, offering adequate sun protection or warmth depending on the weather conditions. Opt for breathable materials like cotton and wool to avoid scalp irritation and overheating.

Investing in a good quality hat ensures not only comfort but also longevity of this versatile accessory in your wardrobe.

Complementing your hairstyle

Finding the right hat to complement your medium-length hairstyle is key to achieving a stylish and put-together look. With so many options available, it’s important to choose a hat style that enhances your hair rather than overpowering it.

For instance, a trilby hat can add a touch of coolness to your medium hair, while a bucket hat frames your face without overwhelming your hairstyle. The bowler hat exudes sophistication, while the cowboy hat gives off a rugged and adventurous vibe.

By investing in the right hat style for your medium-length hair, you can create an overall look that is fashionable and complements your personal style.

11 Great Hat Styles for Men with Medium Length Hair

Here are 11 great hat styles that guys with medium length hair can rock: Trilby, wide brim boonie, bowler hat, baseball cap, knit cap, newsboy cap, cowboy hat, fedora, bucket hat, trucker hat, and Panama hat.


The Trilby hat is a cool and stylish option for guys with medium hair. It gives off an easygoing vibe that can add an extra touch of personality to your look. The Trilby hat has a narrow brim and a deeply indented crown, making it a sophisticated choice for any occasion.

Whether you’re going for a casual or dressed-up look, the Trilby hat will effortlessly elevate your style. So why not give this trendy accessory a try and rock it with your medium-length hair?.

Wide Brim Boonie

The wide brim boonie hat is a fantastic option for men with medium-length hair. Its wide brim helps to provide ample shade and protection from the sun, keeping your scalp cool and preventing any damage to your hair.

The relaxed and laid-back style of the boonie hat perfectly complements medium hairstyles, giving off a casual yet stylish vibe. With its rugged design and practical functionality, the wide brim boonie hat is both fashionable and functional for guys with medium hair.

Knit Cap

A knit cap is a practical and stylish option for men with medium hair. This cozy hat not only keeps your head warm during colder months, but also adds a cool and casual touch to your overall look.

The soft fabric of the knit cap works well with medium-length hairstyles, allowing you to show off your hair while still keeping it under control. Whether you opt for a simple solid color or one with bold stripes or patterns, the knit cap is a versatile accessory that can easily be paired with various outfits.

So grab yourself a trendy knit cap and rock your medium hair in style!

Newsboy Cap

The newsboy cap is a trendy choice for men with medium-length hair, offering a stylish and vintage-inspired look. This hat style features a rounded crown and a stiff brim, creating a unique shape that complements medium hair.

The newsboy cap can be worn in various ways – tilted to the side for added flair or straight on for a more classic look. It adds an effortless touch of sophistication to any outfit, making it an ideal accessory for guys with medium hair who want to elevate their style game.

So go ahead and rock the newsboy cap with confidence!

Cowboy Hat

The cowboy hat is a popular choice for guys with medium hair who want to channel a rugged and adventurous vibe. This iconic hat style adds a touch of Western flair to any outfit, making it a versatile accessory.

With its wide brim and distinctive shape, the cowboy hat helps frame the face while complementing medium-length hairstyles. Whether you’re going for a casual or dressed-up look, the cowboy hat is sure to make a statement and draw positive attention.

So saddle up and rock this stylish hat with confidence!


The fedora is a classic hat style that can add a touch of sophistication to your medium-length hair. This timeless accessory complements various hairstyles and face shapes, making it a versatile choice for any occasion.

With its wide brim and indented crown, the fedora offers both sun protection and style. Whether you’re dressing up or keeping it casual, the fedora is a fashionable option that can elevate your overall look.

Pair it with a button-down shirt and jeans for a polished yet relaxed vibe, or wear it with a tailored suit for a more formal affair. Its timeless appeal makes the fedora an essential addition to any man’s wardrobe.

Trucker Hat

The trucker hat is a popular choice for men with medium hair, adding a casual and laid-back touch to their look. This hat style features a mesh back and an adjustable snapback closure, providing comfort and breathability.

The wide brim helps shield your face from the sun while giving you a cool and rugged appearance. With its versatile design, the trucker hat can be paired with various hairstyles, whether you choose to wear your hair down or tie it up.

Its relaxed vibe makes it perfect for outdoor activities or simply adding some flair to your everyday outfits. Don’t hesitate to rock the trucker hat with your medium-length hair for a stylish and effortless look.

Panama Hat

The Panama hat is a classic and timeless option for men with medium-length hair. It features a wide brim that adds an air of sophistication to any outfit. The lightweight and breathable material make it perfect for warm weather, keeping you cool and stylish at the same time.

With its versatile design, the Panama hat can be paired with both casual and dressier looks, making it a must-have accessory for any man with medium hair. So if you’re looking to elevate your style game, consider adding a Panama hat to your collection.

10. Investing in a good hat is essential for men with medium hair to ensure they have a stylish accessory that complements their hairstyle.

Tips for Wearing a Hat with Medium Hair

Tuck or tie up longer hair to prevent it from getting tangled in the hat.

Tuck or tie up longer hair

For men with medium-length hair, tucking or tying up your longer strands is essential when wearing a hat. This not only prevents your hair from getting flattened or messy under the hat but also allows the hat to sit properly on your head.

Whether you opt for a sleek ponytail, a casual bun, or even just a quick tuck behind your ears, securing your longer hair will give you a polished and put-together look while rocking your favorite hat style.

So don’t forget to tame those locks before putting on that cool accessory!

Experiment with different styles

Try experimenting with different hat styles to find the one that suits your medium hair the best. From trilby hats to wide brim boonies, there are plenty of options to choose from.

Don’t be afraid to try out different looks and see which style complements your hairstyle and face shape. Whether you prefer a fedora or a newsboy cap, finding the right hat can add an extra touch of style and personality to your overall look.

So go ahead, have fun trying out different styles and rock that hat with confidence!

Don’t be afraid to wear your hair down

When it comes to wearing a hat with medium hair, don’t be afraid to let your hair down. Leaving your hair loose and flowing can create a stylish and effortless look when paired with the right hat.

Whether you have wavy locks or straight strands, allowing your medium-length hair to peek out from under the brim of a hat adds an extra layer of charm and personality to your overall style.

Embrace your natural texture or add some volume with products like sea salt spray or texturizing pomade for a relaxed and carefree vibe. So go ahead, rock that hat with confidence and let your medium hair steal the show!

Common Concerns and Solutions

Avoiding hat hair is a common concern, but you can combat it by choosing hats with breathable materials and using dry shampoo to refresh your hair afterwards.

Hat hair

Hat hair is a common concern for guys with medium hair who want to wear hats. However, there are solutions to prevent this issue and still enjoy the benefits of wearing a hat. One way to avoid hat hair is by choosing hats made from materials that reduce friction against the hair, like wool or silk.

Another tip is to apply a small amount of hairspray or styling product before putting on your hat to help keep your style intact. Additionally, consider opting for looser-fitting hats or those with adjustable bands that won’t flatten your hair as much.

With these tips in mind, you can confidently rock a hat without worrying about the dreaded hat hair effect!

Choosing the right size

Finding the right size hat is crucial for men with medium hair to ensure a comfortable and stylish fit. A hat that is too small will feel tight and can leave marks on your forehead, while a hat that is too big will slip down over your eyes and look awkward.

Measure the circumference of your head using a flexible measuring tape and refer to the sizing chart provided by the hat manufacturer to determine your correct size. It’s also important to try on hats before purchasing them, as sizes can vary between brands.

Remember, finding the right fit will not only enhance your overall look but also keep you feeling confident throughout the day.

Finding the right balance between hair and hat

Choosing the perfect hat that complements your medium-length hair can be a game-changer for your overall style. It’s all about finding the right balance between showcasing your hairstyle and wearing a hat that enhances your look.

One way to achieve this is by opting for hats with a wide brim, like the bucket hat or cowboy hat, which frame your face without overwhelming your hair. Another option is the trilby hat, which gives off an easygoing vibe while still allowing you to show off your stylish medium hair.

Don’t forget to consider the size of the hat as well, ensuring it fits properly and doesn’t overshadow your hairstyle. By finding this balance, you’ll rock any hat with confidence and style.


In conclusion, wearing a hat with medium hair is all about finding the right style that complements your hairstyle and face shape. Experiment with different hat options like the trilby, wide brim boonie, or bowler hat to add a touch of coolness and sophistication to your look.

Remember to tuck or tie up longer hair and keep your hat clean for a polished appearance. With the right hat choice, you’ll be able to rock any outfit with confidence and style.


1. What are some stylish ways to wear hats with medium hair for guys?

You can try out many fashionable hairstyles, such as long hair tied up or follow the hat trends for medium-haired men when wearing a hat with your medium-length hair.

2. How do I choose the best hat for my medium length hairstyle?

Selecting the right hat depends on your style and preference; however, there are specific styles that complement men with medium length hairstyles like fedoras or trilbies.

3. Can you suggest any cool ideas to rock a hat with my medium hair?

There are multiple ways to style your medium hair using various hats, from sporting it loose under a beanie or neatly tucked under a baseball cap.

4. Are there any specific fashion tips for wearing hats with medium hair?

Keep in mind that the key is choosing hat styles that add contrast and balance to your face while enhancing your natural features; this could include experimenting with different textures and colors based on current trends.

5. Should I consider accessories when styling my hat look with my medium-length hairstyle?

Yes, certain accessories can enhance the overall look of how you wear a hat; these might include bandanas worn under caps or decorative pins attached to trendy fedoras.

How to Wear a Hat with Medium Hair Guys
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Mila, the veteran beauty cosmetics professional and author of this article, while cutting and styling the hair of her client

Hi! I’m Mila M. I share my 44 year-experience as a Cosmetologist & Beauty Professional in this blog. This content is for educational purposes only and does not constitute professional advice. Consult your trusted Beauty Professional for your personal beauty needs.

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