How to Rock Hats with Medium Hair: A Comprehensive Guide

Looking to add some flair to your medium-length hair with a stylish hat? You’re in the right place!

In this guide, we’ll share some tips and tricks for how to wear hats with medium hair guys without sacrificing your hairdo.

The Best Hats for Medium Hair Guys

Wondering what hats would suit your medium-length hair? Below are some of the best hats for medium hair guys:

1. Baseball Cap

The timeless baseball cap is an excellent choice for an everyday casual look. It is versatile and comes in different designs that make them easy to match with any outfit.

Baseball Cap

2. Newsboy Cap

A classic hat that complements different styles, the newsboy cap is perfect for medium-length hair guys. It provides a vintage feel that works well with tweed jackets and denim jackets.

Newsboy Cap

3. Beanie Hat

If you live in a colder climate, the beanie hat is a go-to option. It is stylish and practical, offering substantial coverage for your head while keeping you warm.

Beanie Hat

4. Fedora Hat

The fedora hat is sophisticated and ideal for formal occasions. It complements business attire, giving a stylish look and matches suits and trousers with perfection.

Fedora Hat

5. Trilby Hat

A stylish hat with a shorter brim, the Trilby hat is perfect for adding elegance to your outfit. It works great with blazers, tweed jackets, and denim outfits.

Trilby Hat

6. Bucket Hat

If you’re looking for a trendy and casual look, the bucket hat is a great option. It has a wide brim and liven up the streetwear, making it an excellent addition to your casual wear collection.

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Bucket Hat

7. Cowboy Hat

If you want to add a western vibe to your outfit, the cowboy hat is an ideal accessory. It complements outdoor activities and is perfect for adventure-seeking individuals.

Cowboy Hat

Note: For an elegant and stylish look, complement your attire with a hat that complements your style, face shape, and matches your outfit. Choose hats that are comfortable, lightweight, and made from breathable fabrics to keep you comfortable all day long.

How to Style Hats with Medium Hair Guys

1. Match the color of your hat with your hair

Matching the color of your hat with your hair is a critical style choice. If you have light hair, go for a darker hat, and if you have dark hair, go for a lighter hat.

Complementing the colors can help you achieve a more natural and refined look.

Medium hair guy wearing a hat with hair matching the hat

2. Style your hair before putting on a hat

Styling your hair before wearing a hat can make a big difference in the outcome of the look. With a little hair spray or pomade, you can ensure that your hair stays in place and avoids hat hair.

Medium hair guy styling hair with hair spray before wearing a hat

3. Wear your hat correctly

Knowing how to wear a hat the right way is crucial to looking fashionable. A baseball cap should be worn forwards or backward, while a fedora or trilby should be slightly tilted forward.

Wearing the hat too low or too high can ruin the look.

Medium hair guy wearing a fedora hat on its tilted position

4. Don’t overdo it

Don’t go overboard with your accessories when wearing a hat. Wearing a watch, necklace, or ring is fine, but keep it simple and avoid wearing too much jewelry as it can take away from the overall look.

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Medium hair guy wearing a baseball cap with a watch

Frequently Asked Questions

Can I wear a hat with any medium hair hairstyle?

Yes, you can wear a hat with any medium hair hairstyle. It's important to ensure that the hat complements your hairstyle and overall look.

How do I care for my hat?

Care for your hat by following the manufacturer's instructions. You can also store your hat in a hat box to prevent it from getting crushed or damaged.

Can I wear a hat indoors?

It's considered impolite to wear a hat indoors, but if you must wear one, ensure that it's a small and casual hat.


Wearing the right hat with your medium-length hair can add a touch of confidence and style. Choose hats that complement your style and match your outfit.

Follow the tips on how to style hats with medium hair guys to achieve the perfect look.


Jonathan B. Delfs

I love to write about men's lifestyle and fashion. Unique tips and inspiration for daily outfits and other occasions are what we like to give you at Do you have any notes or feedback, please write to me directly: [email protected]

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