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How to Wear a Hat With Medium Hair Guys

I've always believed that the right hat can completely transform a look, adding a touch of style and personality. And if you're a guy with medium hair, you're in luck! With the right hat and some expert styling tips, you can take your hairstyle to the next level.

In this article, we'll explore the best hat styles for medium hair guys, understand how to find the perfect fit, and discover some trendy accessories to elevate your look.

So, let's dive in and uncover the secrets of wearing a hat with medium hair!

Key Takeaways

  • Choose a hat style that complements your face shape and personal style.
  • Consider the texture, length, and volume of your hair when selecting a hat.
  • Experiment with different ways of wearing your hat to create unique looks.
  • Keep your hair well-groomed to rock a hat with medium-length hair.

Choosing the Right Hat Style

When choosing the right hat style, it's important to consider the shape of your face. As someone who loves wearing hats and has experimented with various styles, I can confidently say that finding the perfect hat for your face shape can make all the difference.

Whether you have a square, oval, round, or heart-shaped face, there's a hat out there that will enhance your features and add a touch of style to your look.

For those with a square face shape, a hat with a softer, rounded crown can help balance out your strong jawline. Think fedoras or newsboy caps with a slightly slouchy fit.

If you have an oval face shape, you're in luck because you can pull off almost any hat style. From wide-brimmed hats to beanies and baseball caps, the possibilities are endless.

Round-faced individuals should opt for hats with angled brims or tall crowns to create the illusion of length. Trilby hats or bucket hats with a slight tilt can work wonders for your proportions.

Lastly, if you have a heart-shaped face, hats with wide brims or floppy hats will complement your features beautifully. Think Panama hats or wide-brimmed fedoras that add balance to your forehead.

Remember, the key to finding the right hat style is experimentation. Try on different shapes, sizes, and materials until you find the one that makes you feel confident and comfortable. Don't be afraid to step out of your comfort zone and embrace new trends.

With the right hat, you can elevate your style and make a statement wherever you go. So go ahead, find your perfect hat and rock it with confidence!

Understanding Hat Sizing and Fit

When it comes to hats, size matters. Understanding the importance of hat size is crucial in finding the perfect fit that not only complements your style but also ensures maximum comfort.

In this discussion, we will dive into the world of hat sizing and fit, exploring the key points of hat size importance, how to find the perfect fit, and the art of adjusting hat straps to achieve that effortlessly stylish look.

Hat Size Importance

To properly wear a hat with medium hair, you'll want to consider the importance of hat size. It may seem like a minor detail, but the right fit can make all the difference in achieving a stylish and comfortable look. As someone with medium hair, I understand the struggle of finding the perfect hat that doesn't flatten or mess up my hair. That's why understanding hat sizing is essential. Let's take a look at this table to help you determine your hat size:

Hat Size Head Circumference (inches) Head Circumference (cm)
S 21 - 22 53 - 56
M 22 - 23 56 - 58
L 23 - 24 58 - 61
XL 24 - 25 61 - 64

Finding the Perfect Fit

Finding the perfect fit for your hat is crucial in ensuring both style and comfort. As someone with medium hair, I understand the importance of finding a hat that complements my hair length and adds to the overall look.

Here are some tips to help you find the perfect fit:

  • Consider your head shape: Different hats suit different head shapes, so it's important to find one that flatters your features.

  • Measure your head: Knowing your hat size will make it easier to find the right fit and avoid any discomfort.

  • Try different styles: Don't be afraid to experiment with different hat styles to find the one that suits your personal style and hair length.

  • Pay attention to the brim: The brim of the hat should complement your face shape and hair length. It can add a stylish touch to your overall look.

  • Consider the material: Choose a hat made of a material that works well with your hair type and provides maximum comfort.

By following these tips, you'll be able to find a hat that not only fits perfectly but also enhances your overall style.

Adjusting Hat Straps

Make sure you adjust the hat straps to achieve the perfect fit and ensure maximum comfort.

As someone with medium hair, finding the right hat can be a challenge. You want to strike a balance between style and functionality.

When adjusting the hat straps, it's important to consider the shape and size of your head. Start by placing the hat on your head and securing it with the straps. Make sure it sits snugly but not too tight. You don't want it to leave any marks or give you a headache.

Adjust the straps accordingly, making sure they are secure but still allow for some movement. This will ensure that your hat stays in place, even when you're on the go.

With the hat straps properly adjusted, you can confidently rock any hat style and feel comfortable all day long.

Styling Tips for Medium-Length Hair

When styling your medium-length hair, consider using a hat to add a stylish touch to your look. Hats are not only a practical accessory but also a fashion statement that can elevate your style game. Here are some tips to help you rock a hat with your medium-length hair:

  • Find the right hat: Choose a hat that complements your face shape and personal style. Experiment with different styles like fedoras, beanies, or snapbacks to find the perfect match.

  • Consider the hair texture: Depending on the texture of your hair, you can opt for different hat styles. If you have wavy or curly hair, a slouchy beanie can add a relaxed and effortless vibe to your look. For straight hair, a classic fedora can bring a touch of sophistication.

  • Play with proportions: Take into account the length and volume of your hair when choosing a hat. If you have shorter medium-length hair, a smaller hat or a cap can create a balanced and proportionate look. For longer medium-length hair, a wide-brimmed hat can add drama and flair.

  • Don't be afraid to experiment: Hats offer endless possibilities to express your personal style. Try different ways of wearing your hat, such as tilting it to the side or wearing it backwards, to create unique and eye-catching looks.

  • Pay attention to grooming: To rock a hat with medium-length hair, it's essential to keep your hair well-groomed. Regular trims, styling products, and proper hair care will ensure that your hair looks its best under the hat.

Combining Hats With Different Hair Textures

Depending on the texture of your hair, you can try various hat styles to complement your look. As a guy with medium hair, I understand the struggle of finding the perfect hat that not only fits comfortably but also enhances my overall style.

Whether your hair is straight, wavy, or curly, there are hat options that can elevate your fashion game.

For those with straight hair, a classic fedora or a stylish snapback can add a touch of sophistication to your ensemble. The structured silhouette of a fedora creates a sleek and polished look, while a snapback offers a more casual and urban vibe. Both options work well with medium hair, giving it a modern and trendy appeal.

If you have wavy hair, consider trying a beanie or a newsboy cap. These hats embrace the natural texture of your hair, adding a touch of laid-back charm. A beanie can be worn slouchy for a relaxed and effortless look, while a newsboy cap offers a more refined and vintage-inspired style. Either option will effortlessly complement your medium hair, enhancing its natural waves.

For those with curly hair, a bucket hat or a dad hat can be the perfect choice. These hats embrace the volume and texture of your hair, creating a cool and fashion-forward appearance. A bucket hat adds a playful and retro vibe to your look, while a dad hat offers a more casual and sporty aesthetic. Both options work harmoniously with medium curly hair, allowing you to embrace your natural curls while still looking effortlessly stylish.

Hat Accessories for Added Style

If you're looking to amp up your hat game, consider adding accessories for an extra touch of style. Accessories can elevate your outfit and make your hat the focal point of your look. Here are five must-have hat accessories that will take your hat game to the next level:

  • Hat Bands: A hat band is a simple yet effective way to add a pop of color or texture to your hat. Opt for a leather band for a rugged and masculine look, or go for a patterned fabric band for a more playful and eclectic vibe.

  • Pins and Brooches: Pins and brooches are a great way to personalize your hat and show off your unique style. Whether you choose a vintage-inspired pin or a modern brooch, these accessories will add a touch of personality to your hat.

  • Feathers: Feathers are a classic hat accessory that can add a touch of elegance and sophistication to your look. Whether you go for a single feather or a cluster of feathers, they will instantly elevate your hat and give it a distinguished flair.

  • Hatspins: If you want to add a touch of old-world charm to your hat, consider adding a hatpin. These decorative pins not only add style but also keep your hat secure on windy days.

  • Scarves: Scarves are a versatile accessory that can be tied around the base of your hat for a bohemian look or draped over the brim for a chic and sophisticated vibe. Choose a scarf in a bold color or pattern to make a statement.

With these hat accessories in your arsenal, you'll be able to effortlessly elevate your hat game and stand out from the crowd with your unique sense of style. So go ahead, experiment with different accessories and make your hat the ultimate fashion statement.

Hat Etiquette for Various Occasions

Make sure to match the style of your hat to the occasion, as different events may call for different hat etiquette. As someone who loves wearing hats, I understand the importance of choosing the right hat for the right occasion. Whether you're attending a formal event or just going out for a casual outing, your hat can make a statement and add a touch of style to your overall look.

For formal occasions such as weddings or black-tie events, opt for a classic and sophisticated hat like a fedora or a wide-brimmed hat. These styles exude elegance and will complement your outfit perfectly. Remember to remove your hat when you enter a building or when you sit down for a meal, as hat etiquette dictates.

On the other hand, for more casual outings like a day at the beach or a picnic in the park, you can go for a more relaxed and laid-back hat style. A straw hat or a trucker cap can add a cool and effortless vibe to your outfit. Feel free to keep your hat on during these informal occasions, but always be mindful of those around you and remove it when necessary.

No matter the occasion, it's important to wear your hat with confidence and embrace your personal style. Experiment with different hat styles and find the ones that suit you best. Remember, your hat is an extension of your personality, so own it and wear it with pride.

Hat Care and Maintenance

To keep your hats in good condition, it's important to regularly clean and store them properly. As someone who loves hats and knows the importance of caring for them, I want to share my tips on how to keep your hats looking fresh and stylish.

Here are my top hat care and maintenance tips:

  • Regular Dusting: Use a soft brush or lint roller to gently remove any dust or debris from your hats. This will help to keep them looking clean and prevent any buildup over time.

  • Spot Cleaning: If you notice any stains or marks on your hats, don't panic! Use a damp cloth or sponge with a mild soap to gently spot clean the affected area. Be sure to test the soap on a small, inconspicuous area first to ensure it doesn't damage the fabric.

  • Proper Storage: When you're not wearing your hats, it's crucial to store them properly to maintain their shape. Invest in a hat rack or hat box to keep them protected from dust and sunlight. Never store your hats in a humid or damp area, as this can lead to mold or mildew growth.

  • Avoid Excessive Heat: Hats are made from various materials, and some are more heat-sensitive than others. Be cautious when exposing your hats to excessive heat, such as leaving them in a hot car or near a heater, as this can cause them to lose their shape or become damaged.

  • Know When to Retire: As much as we love our hats, they won't last forever. Keep an eye out for signs of wear and tear, such as frayed edges or loose threads. When a hat reaches this point, it's time to retire it and invest in a new one to keep your style game strong.

By following these hat care and maintenance tips, you can ensure that your hats stay in great condition, allowing you to rock them with confidence and style.

Exploring Hat Trends for Medium Hair Guys

When it comes to rocking a hat with medium hair, it's all about finding the perfect style that complements your locks. From classic fedoras to trendy snapbacks, there are endless options to choose from.

But it's not just about the hat; taking care of your hair while wearing one is equally important.

In this discussion, we'll explore the best hat styles for medium hair guys and share some expert haircare tips to ensure your locks stay healthy and stylish.

Best Hat Styles

There's a hat style that goes well with medium hair for guys. It's all about finding the right hat that complements your hair length and adds an extra touch of style to your overall look.

So, let me introduce you to the best hat styles for medium-haired gentlemen:

  • The Classic Fedora: This timeless hat exudes sophistication and can instantly elevate your outfit.

  • The Newsboy Cap: With its vintage charm, this cap adds a touch of nostalgia to your ensemble.

  • The Trilby Hat: This stylish hat adds a modern twist to your medium hair, making you look effortlessly cool.

  • The Flat Cap: Perfect for a casual and laid-back vibe, this hat adds a touch of charm to any outfit.

  • The Baseball Cap: This versatile and sporty hat is a go-to for a relaxed, everyday look.

Haircare Tips for Hats

One way to keep your hair looking great while wearing a hat is to style it in a way that prevents it from getting flattened.

As someone who loves hats and takes pride in my hair, I've learned a few tricks to keep my locks looking fabulous even with a hat on.

Firstly, try adding some volume to your hair by using a volumizing spray or mousse before styling. This will help create a fuller look that can withstand the pressure of a hat.

Secondly, consider opting for a looser fitting hat that won't press down too heavily on your hair.

Lastly, try styling your hair in a way that adds height, such as a messy quiff or a tousled side part. This will give your hair some dimension and prevent it from looking flat when you take off your hat.

Frequently Asked Questions

How Do I Determine My Hat Size?

To determine my hat size, I measure the circumference of my head just above my ears using a flexible measuring tape. Then, I consult a hat size chart to find the corresponding size.

Can I Wear a Hat With Shorter Hair?

I love wearing hats, even with shorter hair! It's all about finding the right hat style that complements your face shape and personal style. Experiment with different brim widths and materials to find your perfect match.

What Are Some Hairstyles That Work Well With Hats?

Some hairstyles that work well with hats include messy buns, low ponytails, and textured waves. These styles add a touch of effortless coolness to any hat-wearing look, making you the trendsetter of the day.

Are There Specific Hats That Should Be Avoided for Medium-Length Hair?

Are there hats that should be avoided for medium hair guys? Absolutely! Some hats may flatten your hair or make it look messy. Stick to hats with a wider brim or adjustable sizing for a stylish look.

How Can I Style My Hair to Avoid Hat Hair After Wearing a Hat?

To avoid hat hair after wearing a hat, I usually style my hair with a lightweight, volumizing product. I also make sure my hair is completely dry before putting on the hat to minimize the flattening effect.


In conclusion, wearing a hat with medium hair guys is not just about style, but also about embracing your unique personality. By choosing the right hat style and understanding hat sizing and fit, you can enhance your overall look.

Styling tips for medium-length hair can help you create a harmonious balance between your hair and hat. Combining hats with different hair textures can add an extra dimension to your outfit.

Hat accessories can elevate your style to the next level. And remember, hat etiquette and care are essential for any occasion.

So go ahead, explore the world of hats and let your medium hair shine!


Embracing the art of grooming, I offer a comprehensive guide to men's skincare and style. From tailored grooming routines to timeless fashion advice, I'm here to elevate your personal image. Let's embark on a journey of refinement and self-expression, one step at a time.

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