15 Stylish Medium-Length Messy Hairstyles for Men

Medium messy hairstyles are a favorite among guys for a reason—they’re simple to style and give off that effortless, “just rolled out of bed” look that everyone loves. With that in mind, we’ve curated a collection of messy hairstyles that men can create in five minutes or less.

We’ve covered a range of different messy hairstyles so that every guy can find something that fits his style. Whether you’re going for a laid-back vibe or something a little more polished, there’s sure to be a look here for you.

1. The Thick Hair Solution

Thick hair can be your secret weapon when it comes to messy hairstyles. The natural volume and density of thicker hair create a more defined and dynamic look, making your style appear effortlessly cool without much effort. A little tousle can go a long way when you have more hair, allowing you to achieve that perfect blend of messy yet intentional.

For thick-haired guys, this style is ideal because it embraces the texture instead of fighting it. You can easily add a bit of lightweight styling product, like a texturizing spray or matte pomade, to enhance the natural body and maintain some control. The result? A voluminous, carefree look that feels fresh yet low-maintenance. Whether you prefer a loose fringe, a messy quiff, or simply letting your hair do its thing, thick hair makes messy styles feel naturally fuller and bolder.

The best part? It’s versatile enough for any occasion, whether you’re heading to work or out with friends.

2. Messy Style for Thinning Hair

If you’re experiencing hair loss or thinning, a messy hairstyle can be a fantastic solution. This style looks effortlessly cool and creates the illusion of thicker, fuller strands, helping to boost your confidence.

The key to achieving this look is to embrace texture and volume. Start by using a volumizing shampoo and conditioner to add somebody to your hair during your washing routine. After towel-drying your hair, apply a lightweight styling product, such as a mousse or a texturizing spray, which will help lift your roots and create that messy effect without weighing your hair down.

When styling, use your fingers to tousle your hair, focusing on the roots to create height. A “dry shampoo” can also work wonders by adding texture and absorbing excess oil, making it an excellent option for adding that much-needed lift. For an even more casual look, consider using a salt spray to enhance the natural waves and create a beachy vibe.

One significant advantage of a messy style is that it can be customized to suit your personal taste. Whether you prefer a slightly more polished finish or a full-on tousled look, this hairstyle can be easily adjusted. Additionally, you can incorporate a side part or a textured fringe to help frame your face, diverting attention away from thinning areas.

Remember, a messy hairstyle not only gives you a fresh and modern appearance but also serves as a clever way to manage thinning hair. Embrace the messy look and enjoy the benefits of a style that combines confidence with effortless flair!

3. Spiked Up Front

Try spiking up the front of your hair for a more controlled take on the messy look. All it takes is a small amount of hair gel or styling paste to lift the front and give your style some texture without going overboard. It’s the ideal balance between neat and laid-back, allowing you to keep the messiness subtle while still adding a bit of edge.

This style works particularly well for guys who want a clean yet casual vibe. By keeping the rest of the hair relaxed and focusing on the front, you create a cool, structured look that isn’t too polished. Plus, it’s a simple way to add volume and dimension to your strands, making it a great go-to for days when you want to keep things effortless but stylish.

4. The Messy Man Bun

The messy man bun is a fantastic hairstyle that has gained popularity among men, and for a good reason. Just like the classic messy bun that many women adore, the messy man bun combines style and practicality, making it a must-try for guys with longer hair. This trend allows you to embrace your longer strands while keeping them out of your face, making them both fashionable and functional.

To create the perfect messy man bun, start by gathering your hair at the crown of your head or slightly lower, depending on your preference. Use a hair tie to secure it in place, but don’t worry about making it too tight or perfect. The charm of the messy man bun lies in its carefree aesthetic, so let a few strands fall loose around your face to add to that effortless vibe.

You can even pull some hair out at the sides for a softer look or leave the bun a bit loose for a more relaxed appearance. For added texture and grip, consider using a bit of styling cream or sea salt spray before tying it up. This will give your bun a bit of hold while maintaining that laid-back feel.

Whether you’re heading to the gym, out for a casual date, or just lounging at home, the messy man bun is the perfect way to express your style while keeping things practical and comfortable. Plus, it’s a great way to channel that rugged, effortlessly cool look that so many strive for!

5. Effortless Short Messy Hair

Effortless short messy hair is the epitome of laid-back style, allowing you to embrace your hair’s natural texture without the fuss of heavy styling products. This look celebrates simplicity and authenticity, making it a go-to choice for guys who want to look sharp while keeping things easy.

To achieve this effortless style, start with clean, dry hair. Instead of reaching for gels or pomades, simply allow your hair to air dry after washing. If you prefer a bit of texture, you can lightly towel dry your hair and let it dry naturally. As it dries, it will fall into its natural shape and texture, giving you that carefree appearance.

Once your hair is dry, use your fingers to tousle it gently. Focus on the crown and tips, lifting sections to create volume and a bit of movement. The beauty of this style is that it’s completely customizable; whether you have straight, wavy, or curly hair, this look works with what you have.

If you find your hair needs a little boost or you want to enhance its natural texture, consider spritzing on a bit of sea salt spray or a lightweight texturizing mist. This will add definition without making your hair feel heavy or sticky.

Effortless short messy hair is perfect for any occasion—from casual outings to work environments—because it strikes a perfect balance between relaxed and polished.

6. Messy White Hair

Messy white hair is a style that transcends age, proving that looking effortlessly cool is not confined to the young. This look embraces the natural beauty of white or gray hair while adding a touch of playfulness and individuality. The key to pulling off this hairstyle is to celebrate your hair’s unique texture and color, allowing it to shine in its own right.

To achieve this style, simply use a lightweight styling cream or texturizing spray to tousle your hair, creating the desired messy effect. Focus on adding volume and movement, allowing your strands to fall naturally. The beauty of messy white hair is that it often appears more dynamic and interesting than a perfectly styled look, making it a great choice for those who want to showcase their personality.

Pairing your messy white hair with a well-groomed beard can also enhance the overall appearance, giving the look a more youthful spin. A trimmed beard adds structure and balance, framing your face beautifully while accentuating your hair’s unique texture.

This hairstyle is versatile enough for both casual outings and more formal events. Whether you’re enjoying a weekend brunch with friends or attending a family gathering, messy white hair allows you to express your style confidently. Embrace this trend and show the world that age is just a number; style is timeless!

7. Spiky Messy Hair

If you want to embrace a messy hairstyle while still maintaining some structure, spiky messy hair is an excellent option. This look allows you to express individuality while keeping your strands intentional and stylish. With the right product, you can create a spiky texture that captures that laid-back vibe without sacrificing style.

To achieve this look, start by applying a small amount of AXE Clean Cut Look: Classic Pomade to your fingertips. This product is perfect for adding texture and definition without making your hair feel stiff or weighed down. Run your fingers through your damp or dry hair, focusing on the areas you want to spike up. Use your fingers to twist and shape the strands, creating that coveted, messy appearance.

One of the great things about using pomade is that it gives you the flexibility to mold your hair while still allowing for movement. You can create spikes that look effortlessly tousled, giving you a carefree yet polished finish. Whether you prefer a more dramatic look with pronounced spikes or a subtle, messy style, pomade allows you to customize your hairstyle to suit your mood.

8. Messy Hair Boy Looks: Wet Hair

Embracing the messy hair boy trend has never been easier, and one of the most popular variations is the wet hairstyle. This look exudes a relaxed yet stylish vibe, perfect for achieving that effortless, just-out-of-the-shower aesthetic. Here’s how to nail this trendy style with minimal effort.

To create a wet hair look, start by brushing your hair forward. This helps lay the foundation for the style while adding a touch of dimension. Next, reach for a flexible hold hairspray like Dove Style+Care Flexible Hold Hairspray. This product is perfect for maintaining your hairstyle without the stiffness or crunchiness of more potent sprays.

Lightly spritz the hairspray throughout your damp hair. The flexible formula allows your hair to retain its natural movement while holding everything in place. Depending on your preference, you can run your fingers through your hair to create a more tousled effect or use a comb for a sleeker finish.

This versatile wet hairstyle works well for various occasions, whether heading to school, hanging out with friends, or going out for a casual date. It’s a great way to showcase your laid-back style while keeping your look polished and put together.

9. Windblown Messy Hair

The windblown messy hair look is a timeless, effortlessly cool style that captures that carefree spirit as if you’ve just hopped off your motorcycle and run your fingers through your hair. This look not only exudes rugged charm but also embodies a sense of adventure and spontaneity.

To achieve this irresistible hairstyle, start with dry, clean hair. A little bit of natural texture works wonders, so if your hair is a bit flat, consider using a volumizing spray or dry shampoo to add some lift. Once your hair is prepped, the key to creating the windblown effect is to use a texturizing spray or sea salt spray.

Spritz the product evenly throughout your hair, then use your fingers to tousle and scrunch your strands. This will create that tousled, just-got-out-of-the-wind look. Focus on the mid-lengths and ends of your hair, allowing the roots to stay slightly less defined for a more natural appearance.

For added dimension, run a few strands through a curling wand on a low heat setting to create loose waves that mimic the windswept effect. Finish off with a light-hold hairspray to keep everything in place while still allowing for movement.

This windblown messy hairstyle is incredibly versatile and perfect for any casual occasion, whether you’re hitting the road or grabbing coffee with friends. It’s an effortlessly stylish choice that brings an element of adventure to your look, making you feel as daring as you look!

10. A Grungy Messy Style

The grungy messy style is the perfect fusion of laid-back messiness and edgy attitude, making it a standout choice for those who want to make a statement. This look combines the carefree essence of messy hair with the rebellious flair of grunge, resulting in a hairstyle that exudes effortless cool.

To achieve this trendy style, start with slightly dirty or second-day hair, which naturally holds texture better than freshly washed locks. Use a texturizing spray or dry shampoo to create the lived-in, gritty look characteristic of grunge aesthetics. These products add volume and separation, helping you achieve the perfect balance of tousled and untamed.

Next, focus on adding some definition to your strands. Use your fingers to create loose waves or curls, allowing your hair to fall naturally into place. You can also rough up the ends for a more disheveled effect. If you have longer hair, consider incorporating choppy layers or an asymmetrical cut to enhance the grunge vibe further.

For a finishing touch, don’t shy away from a little messiness. Let some pieces hang loose around your face, and avoid over-styling or smoothing the look. The essence of this hairstyle lies in its imperfect charm, so embrace those flyaways and textured bits.

One of the best aspects of the grungy messy style is its versatility. Whether you’re heading to a casual hangout, a concert, or even a laid-back workplace, this hairstyle fits a wide range of occasions. Pair it with a leather jacket or a band tee for a complete grunge look, or keep it simple with jeans and a casual shirt.

11. Business Casual

If you’re worried that a messy hairstyle won’t work in a professional environment, fear not! The business casual messy style proves you can achieve a polished look while embracing a touch of laid-back charm. This clean-cut approach allows you to maintain a professional appearance without sacrificing your personal style.

To create a business casual messy hairstyle, start with well-groomed hair that’s clean and free from excessive oil or product buildup. The key here is to incorporate a subtle messiness that looks intentional rather than unkempt. Begin by applying a lightweight styling cream or pomade to add a bit of texture and control.

Style your hair by brushing it back or to the side, depending on your preference and face shape. Allow some strands to fall naturally for a relaxed vibe, but keep it neat enough to look professional. A slight side part can add an air of sophistication while still allowing for that messy aesthetic.

For added texture, you can use a texturizing spray to create gentle waves or volume. Just a few spritzes can help your hair look fuller and more dynamic without feeling heavy or over-styled. The goal is to strike a balance between polished and carefree.

Finish the look with a light-hold hairspray to ensure your style stays in place throughout the day. This allows for some movement while keeping everything neatly in check.

The business casual messy style is versatile and appropriate for a range of work environments. Whether you’re heading to a meeting, engaging in team collaborations, or meeting with clients, this hairstyle helps you present yourself confidently and stylishly.

12. Stick Straight

The stick straight hairstyle is a bold and edgy look that adds height and definition to your overall appearance. By using gel to elevate the front center section of your hair, you create a striking silhouette that not only stands out but also exudes confidence and style. This look is perfect for anyone wanting to make a statement while maintaining control and light hold.

To achieve the stick straight style, start with clean, damp hair. Apply a small amount of styling gel to your fingertips, focusing on the front section of your hair. It’s important to choose a gel that offers a light hold; you want to create volume and texture without making your hair feel stiff or crunchy.

Begin by working the gel through your hair, concentrating on the roots of the front section. Use your fingers to lift the hair straight from the scalp, creating height. As you style, you can use a comb or your fingers to shape the hair into a more defined point at the top for added drama.

Once you’ve achieved your desired height, you can leave the rest of your hair down or slick it back for a more polished appearance. If you choose to keep the remaining hair down, consider adding a bit of texturizing spray to enhance the overall look, giving it a fresh and dynamic feel.

13. Loose Curls

If you’re looking for a messy hairstyle that embodies effortless style, loose curls are a fantastic option. This look is all about embracing natural texture and adding a bit of bounce to your hair, creating a laid-back vibe that is both stylish and easy to maintain. The longer your hair grows, the more room you have to play with curls, making it the perfect messy style for men.

To achieve loose curls, start by allowing your hair to grow out to a medium or longer length. Once you have the length, you can use a few simple techniques to create those sought-after curls without spending hours styling.

Prep Your Hair: Start with clean, damp hair. Apply a curl-enhancing cream or lightweight mousse to add some texture and help define the curls. This will not only enhance your natural waves but also provide some hold.

Create Curls: You can either use a curling wand for a more defined look or let your hair air-dry naturally to embrace its natural wave. If using a curling wand, wrap sections of hair around the barrel, holding for a few seconds before releasing. For a more relaxed curl, use a larger barrel size.

Tousle for Texture: Once your curls are set, use your fingers to tousle and separate them gently. This will create that messy, carefree appearance. Avoid using a comb or brush, which can make your curls frizzy.

Finish with Product: Lightly spray with a flexible hold hairspray or a texturizing spray to help maintain the shape without making your hair feel crunchy or stiff. This will allow your curls to move while keeping the messy style intact.

14. One-Sided Messy Style

The one-sided messy style is a trendy, sophisticated look that effortlessly blends casual flair with polished elegance. By utilizing gel to create volume on one side of your hair, you can achieve a unique and eye-catching hairstyle that works perfectly for various occasions, from casual outings to fancier events.

Begin with freshly washed and completely dry hair. This style looks best with a bit of natural texture. If your hair is flat, consider using volumizing shampoo and conditioner beforehand.

Take a small amount of styling gel and rub it between your palms. Focus on a lightweight gel that provides a good hold without making your hair feel stiff. Apply the gel mainly to the side you want to enhance, working it through the hair from roots to tips.

Use your fingers to lift the hair at the roots on the chosen side, creating a voluminous look. To add an extra lift, you can also use a hair dryer with a diffuser attachment on a low heat setting. For more texture, consider scrunching the hair as you dry.

Once you’ve achieved the desired volume, use a comb or your fingers to sweep the hair over to one side. Because of that messy aesthetic, you can either keep it sleek and controlled or let it fall more casually.

If you want a more tousled effect, lightly pull apart some strands to create texture. For added definition, consider using a texturizing spray to enhance the overall look without adding weight.

Finish with a light-hold hairspray to keep everything in place while still allowing for movement. This ensures your style remains intact throughout the day or night.

One of the best aspects of the one-sided messy style is its versatility. This look can seamlessly transition from a casual day out with friends to a more upscale event or dinner. Pair it with a smart casual outfit for a date night, or keep it laid-back with a graphic tee and jeans.

15. Dreadlocks Style

Dreadlocks are a bold and expressive hairstyle that can reflect your individuality and creativity. Whether you’re considering starting your dreadlock journey or looking for new ways to style your existing locks, this versatile look offers endless possibilities. From classic, free-flowing dreadlocks to stylish updos, a dreadlock style suits every occasion.

If you’re new to dreadlocks and eager to try them out, it’s essential to understand the process involved. Creating dreadlocks typically requires patience and commitment as they develop over time. Choose a method that suits your hair type and personal preference, such as the twist and rip method, backcombing, or free-forming. Start by dividing your hair into even sections to ensure uniformity in size. The size of each section will determine the thickness of your dreads.

Once you’ve sectioned your hair, create the dreads according to your chosen method, either by twisting and securing the sections, backcombing them, or allowing your hair to naturally form locks over time. Regular maintenance is crucial for keeping your dreadlocks looking fresh. This includes palm-rolling your locks, retwisting new growth, and using products designed explicitly for dreadlocks to avoid buildup.

If you already have dreadlocks, you can play with different styles to keep your look fresh and exciting. For a clean and stylish look, gather your dreadlocks into a high or low ponytail. This is an excellent option for keeping hair off your face while showcasing your locks. Alternatively, you can twist your dreadlocks into a bun at the back of your head for a more relaxed vibe. This style is perfect for warm weather or when you want a laid-back appearance, and you can let a few loose strands frame your face for a softer look. Another option is the half-up, half-down style, which enables you to keep some locks out of your face while letting the rest flow freely. Simply gather the top half of your dreadlocks and secure them with a hair tie or clip.

Dreadlocks are incredibly versatile and can be styled to suit any occasion, from casual outings to formal events. They can make a bold statement or provide a relaxed, bohemian vibe, depending on how you choose to wear them.