15 Stylish Medium-Length Messy Hairstyles for Men

Medium messy hair is a guy’s favorite for a reason – it’s easy to style and gives off that “just rolled out of bed” look everyone loves. So, we’ve assembled a collection of messy hairstyles that can be done in 5 minutes or less.

We’ve got a range of messy hairstyles, so every guy can find something that fits his style. Whether you’re going for laid-back or edgy and trendy, we’ve got you covered.

What is a Messy Hairstyle?

A messy hairstyle is a relaxed, undone look that’s both casual and stylish. It can be done with any hair length and texture, so whether you have straight hair, wavy hair, or curly hair, a messy hairstyle can be tailored to your style. It’s often associated with laid-back, casual occasions but can be dressed up for more formal occasions. It’s versatile and timeless.

1. The Thick Hair Solution

Thick, medium-length hair is your best friend when it comes to messy hair. The natural volume and density of thicker hair give you a more defined and dynamic look. You can look cool without trying. A little tousle can go a long way when you have more hair. You can get that messy and intentional look.

Fringe haircuts, such as textured, side-swept, and blunt fringes, can enhance facial features and follow current grooming trends. These styles are versatile and sophisticated, so they’re a popular choice for modern men.

For thick-haired guys, this style is perfect because it works with the texture, not against it. You can add a lightweight styling product like a texturizing spray or matte pomade to enhance the natural body and some control. The result? A voluminous, carefree look that feels fresh and low-maintenance. Whether you like a loose fringe, a messy quiff, or just letting your hair do its thing, thick hair makes messy styles look fuller and bolder.

The best part? It’s suitable for any occasion, whether you’re going 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 great solution. It looks cool and creates the illusion of thicker, fuller hair, which will boost your confidence.

The key to this look is to work with texture and volume. Start by using a volumizing shampoo and conditioner to add somebody to your hair during your washing routine. After towel drying, apply a lightweight styling product like a mousse or texturizing spray to your hair, which will lift your roots and give you that messy look without weighing your hair down.

When styling, use your fingers to tousle your hair, focusing on the roots to add height. A “dry shampoo” can also work wonders by adding texture and absorbing excess oil; it’s a great option to add that extra lift. For a more relaxed look, use a salt spray to enhance the natural waves and get that beachy vibe.

One of the best things about a messy style is that you can customize it to your taste. Whether you like a slightly more polished finish or a full-on tousled look, this style can be adjusted. You can also use a side part or a textured fringe to frame your face and draw attention away from thinning areas.

Remember, a messy style looks fresh and modern and is also a clever way to manage thinning hair. Go messy and enjoy the benefits of a confident and effortless style!

3. Spiked Up Front

Try spicing up the front of your hair for a more polished, messy look. Just a small amount of hair gel or styling paste will lift the front and give you texture without going overboard. It’s the perfect balance between neat and laid-back, so you can keep the messiness subtle and add a bit of edge.

This works well for guys who want a clean but casual look. By keeping the rest of the hair relaxed and focusing on the front, you get a cool, structured look that’s not too polished. Plus, it’s an easy way to add volume and texture to your hair, so it’s an excellent option for days when you want to look effortless but stylish.

4. The Messy Man Bun

The messy man bun is a great hairstyle that’s become popular among men, and for good reason. Just like the classic messy bun that many women love, the messy man bun is stylish and practical, so it’s a must-try for guys with long hair. This trend lets you wear your longer hair and keep it out of your face so it’s both fashionable and functional.

To do the 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 is in its carefree look, so let a few strands fall out around your face to add to that effortless vibe.

You can pull some hair out at the sides for a softer look or leave the bun loose for a more relaxed look. For added texture and grip, use a bit of styling cream or sea salt spray before tying it up. This will give your bun some hold, but still keep it laid back.

Whether you’re going to the gym, on a casual date, or just lounging at home, the messy man bun is the perfect way to express yourself while keeping it practical and comfortable. Plus, it’s a great way to channel that rugged, effortless cool that we all strive for!

5. Effortless Short Messy Hair

Effortless, short, messy hair is the ultimate laid-back style. You can just let your hair be and not worry about using heavy products. This style is all about simplicity and authenticity, so it’s a go-to for guys who want to look sharp but easy.

To do this style, start with clean, dry hair. Instead of reaching for gels or pomades, just let your hair air dry after washing. If you want 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 effortless look.

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

If you need a bit of extra oomph or want to enhance your natural texture, use a bit of sea salt spray or a light texturizing mist. This will add definition without making your hair feel heavy or sticky.

Effortless, short, messy hair is suitable for any occasion – from casual to work environments – because it’s perfectly balanced between relaxed and polished.

6. Messy White Hair

Messy white hair is an ageless style, proving that you don’t have to be young to look effortlessly cool. This style celebrates the natural beauty of white or gray hair and adds a bit of fun and individuality. The key to pulling this off is to let your hair be and let it shine in its own right.

To do this style, use a light styling cream or texturizing spray to rough up your hair and create a messy effect. Focus on adding volume and movement, and let your strands fall naturally. The beauty of messy white hair is that it’s often more dynamic and interesting than a perfectly styled look, so it’s a great choice for those who want to show off their personality.

Pairing your messy white hair with a well-groomed beard will also enhance the overall look and give it a more youthful spin. A trimmed beard adds structure and balance, frames your face beautifully, and highlights your hair’s texture.

This style is good for both casual and formal occasions. Whether you’re having a weekend brunch with friends or a family gathering, messy white hair allows you to express yourself. Embrace this trend and show the world age is just a number; style is timeless!

7. Spiky Messy Hair

If you want to go messy but still have some structure, spiky, messy hair is the way to go. This style allows you to express yourself while keeping your strands intentional and stylish. With the right product, you can create a spiky texture that’s laid-back without sacrificing style.

To do this style, apply a small amount of AXE Clean Cut Look: Classic Pomade to your fingers. This product is perfect for adding texture and definition without making your hair feel stiff or heavy. 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 to create a messy effect.

One of the best things about using pomade is it gives you the flexibility to mould your hair while allowing movement. You can create spikes that look like you just rolled out of bed and still look polished. Whether you want a more dramatic look with big spikes or a subtle, messy look, pomade lets you customize your style to 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 look. This style is relaxed and stylish, perfect for that effortless, just-out-of-the-shower look. Here’s how to do this style with minimal effort.

To give your hair a wet look, brush it forward. This sets the foundation for the style and adds some dimension. Next, grab a flexible hold hairspray like Dove Style+Care Flexible Hold Hairspray. This product is perfect for holding your style without the stiffness or crunchiness of a stronger spray.

Spray the hairspray all over your damp hair. The flexible formula allows your hair to move while holding everything in place. You can run your fingers through your hair to create a more messy effect or use a comb for a sleeker look.

This wet style is good for any occasion, whether you’re going to school, hanging out with friends, or on a casual date. It’s a great way to show off your relaxed style while still looking polished.

9. Windblown Messy Hair

The windblown messy hair look is a classic, cool style that looks like you just hopped off your motorcycle and ran your fingers through your hair. This style is rugged and adventurous, and a trendy variation of this is the messy fade, which is a messy top with a faded haircut. It is modern and low-maintenance.

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

Spray the product all over your hair, then use your fingers to scrunch and tousle your strands. This will create the tousled, just-got-out-of-the-wind look. Focus on the mid-lengths and ends of your hair, and leave the roots a bit less defined for a more natural look.

For extra dimension, run a few strands through a curling wand on a low heat setting to create loose waves that look like the windblown effect. Finish with a light-hold hairspray to hold everything in place while allowing movement.

This windblown messy style is good for any casual occasion, whether hitting the road or grabbing coffee with friends. It’s a stylish choice that adds an element of adventure to your look and makes you feel as bold as you look!

10. Grungy Messy

The grungy, messy style is laid-back, messy, and edgy, perfect for those who want to make a statement. It combines the carefreeness of messy hair with the rebelliousness of grunge—it’s a style that looks effortlessly cool.

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

Next, add some definitions to your strands. Use your fingers to create loose waves or curls and let your hair fall naturally into place. You can also rough up the ends for a more messy look. If you have longer hair, consider choppy layers or an asymmetrical cut to add to the grunge vibe.

Finish off with a bit of mess. Let some strands hang around your face, and don’t overstyle or smooth the look. The beauty of this style is in its imperfection, so let those flyaways and textured bits be.

One of the best things about the grungy, messy style is its versatility. Whether you’re going to a casual hangout, a concert, or even a laid-back workplace, this style fits any occasion. Pair it with a leather jacket or a band tee for a full-on grunge look, or keep it simple with jeans and a casual shirt.

11. Business Casual

If you think messy hair won’t work in a professional environment, fear not! The business casual messy style proves you can look polished while still being laid-back. This clean-cut approach allows you to look professional without sacrificing your personal style.

To do a business casual messy style, start with clean hair that’s not too oily or product-built up. The key here is to add a subtle messiness that looks intentional, not unkempt. Begin by applying a light-hold styling cream or pomade to add texture and control.

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

For extra texture, use a texturizing spray to create gentle waves or volume. A few spritzes can make your hair look fuller and more dynamic without feeling heavy or overstyled. The goal is to look polished and carefree.

Finish off with a light-hold hairspray to keep your style in place all day. This allows for some movement while keeping everything in check.

The business casual messy style is versatile and works in any work environment. Whether you’re going to a meeting, team collaboration, or a client meeting, this style helps you look confident and stylish.

12. Stick Straight

The stick-straight style is bold and edgy, adding height and definition to your overall look. By using gel to lift the front center section of your hair, you create a strong silhouette that stands out and looks confident and stylish. It is perfect for anyone who wants to make a statement and has control and light hold.

To do the stick-straight style, start with clean, damp hair. Apply a small amount of styling gel to your fingers and focus on the front section of your hair. Make sure to use a light hold gel if you want to add volume and texture without making your hair feel stiff or crunchy.

Begin by working the gel through your hair, focusing 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 point at the top for extra drama.

Once you have your desired height, you can leave the rest of your hair down or slick it back for a more polished look. If you leave the rest of your hair down, you can add a bit of texturizing spray to enhance the look and give it a fresh and dynamic feel.

13. Loose Curls

If you want a messy style that looks effortless, loose curls are the way to go. This look is all about embracing your natural texture and adding a bit of bounce to your hair to create a laid-back look that’s stylish and low-maintenance. The longer your hair, the more you can play with curls, so it’s the perfect messy style for men.

To do loose curls, start by growing your hair out to a medium or longer length. Once you have the length, you can use a few simple techniques to create those curls without spending hours styling.

Prep Your Hair: Start with clean, damp hair. Apply a curl-enhancing cream or lightweight mousse to add texture and help define the curls. This will enhance your natural waves and give you some hold.

Create Curls: You can use a curling wand for a more defined look or let your hair air dry to let your natural wave do the work. If using a curling wand, wrap sections of hair around the barrel and hold 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 them and separate them gently. This will give you that messy look. Don’t use a comb or brush, as this will frizz your curls.

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

14. One-Sided Messy Style

The one-sided, messy style is a trendy, stylish look that combines casual with polished. By using gel to add volume to one side of your hair, you can create a one-of-a-kind look that’s perfect for any occasion, from casual to fancy.

Start with freshly washed and dry hair. This look is best with a bit of natural texture. If your hair is flat, use volumizing shampoo and conditioner beforehand.

Take a small amount of styling gel and rub it between your palms. Go for a lightweight gel that has a good hold without making your hair feel stiff. Apply the gel to the side you want to enhance and work it through the hair from roots to ends.

Use your fingers to lift the hair at the roots on the chosen side to create volume. To add extra volume, you can also use a hair dryer with a diffuser attachment on a low heat setting. For more texture, scrunch the hair as you dry.

Once you have the volume, use a comb or your fingers to sweep the hair to one side. Because of the messy look, you can either keep it sleek and tidy or let it feel more relaxed.

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

Finish with a light-hold hairspray to keep everything in place while allowing movement. This will keep your style all day or night.

One of the best things about the one-sided, messy style is its versatility. This look can go from a casual day out with friends to a fancy event or dinner. Wear a smart casual outfit for a date night, or keep it laid-back with a graphic tee and jeans.

15. Dreadlocks

Dreadlocks are a bold and expressive hairstyle that reflects your individuality and creativity. Whether you’re starting your dreadlock journey or looking for new ways to style your existing locks, this style has endless options. From classic free-flowing dreadlocks to updos, a dreadlock style is for every occasion.

If you’re new to dreadlocks and want to try them out, it’s important to understand the process. Creating dreadlocks takes time and commitment as they develop over time. Choose a method that suits your hair type and personal preference: twist and rip, backcombing, or free-forming. Divide your hair into even sections to ensure uniformity in size. The size of each section will determine the thickness of your dreads.

Once you have sectioned your hair, create the dreads according to your chosen method, either by twisting and securing the sections, backcombing them, or letting your hair form locks over time. Regular maintenance is key to keeping your dreadlocks looking fresh. This includes palm rolling your locks, retwisting new growth, and using products specifically for dreadlocks to avoid buildup.

If you already have dreadlocks, you can play with different styles to keep your look fresh and interesting. For a clean and stylish look, gather your dreadlocks into a high or low ponytail. This is a great way to get your hair out of your face and show off your locks. Or 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 to look laid back, and you can let a few loose strands frame your face for a softer look. Another option is the half-up, half-down style, where you can keep some locks out of your face and let the rest flow. Simply gather the top half of your dreadlocks and secure them with a hair tie or clip.

Dreadlocks are versatile and can be styled for any occasion, from casual to formal. Depending on how you wear them, they can make a statement or be bohemian.