Messy hairstyles are a great way to look stylish without putting in too much effort.
They give off a relaxed, natural vibe that works for any occasion.
Whether you have short, medium, or long hair, there’s a messy style that suits your personality.
From tousled crops to textured waves, these looks make you stand out without looking overdone.
In this article, I’ll show you 24 messy hairstyles for men to look effortlessly cool and confident.
1. Textured Messy Crop with Tapered Sides
This textured crop with messy layers gives a relaxed yet stylish appeal. The tapered sides keep the look fresh, while the tousled top adds a modern edge. Paired with a leather jacket, it exudes effortless confidence, making it perfect for casual outings or nightlife. The slightly disheveled style is easy to maintain, requiring just a touch of matte styling product.
2. Messy Wavy Fringe with Natural Volume
Wavy fringes are ideal for a carefree yet fashionable look. The natural waves add dimension, creating a soft, unstructured style that works for any occasion. A bit of lightweight mousse enhances the movement, making it appear windswept and effortless. The urban background further enhances the relaxed, stylish appeal, making this a great choice for men who love a casual yet put-together appearance.
3. Tousled Quiff with a Laid-Back Appeal
A tousled quiff blends structure with spontaneity, offering a perfect mix of refinement and ease. The natural texture gives the quiff a casual, lived-in feel, while the slight lift at the front enhances volume. This look is perfect for men who want a stylish but low-maintenance hairstyle that transitions smoothly from day to night. A touch of sea salt spray helps achieve the airy texture effortlessly.
4. Messy Shag with Loose Layers
This modern shag is the perfect embodiment of effortless cool. The natural waves and layered texture make it a versatile choice for men who love a free-spirited look. Whether left to air dry or slightly tousled with a styling cream, this hairstyle radiates laid-back confidence. The longer layers provide a stylish, bohemian feel, making it ideal for those who prefer a relaxed, artsy appearance.
5. Messy Side-Swept Undercut
The contrast between a sharp undercut and a messy top creates a bold yet relaxed appearance. Sweeping the hair to one side adds dimension, while the textured finish keeps it modern and stylish. A matte pomade enhances the tousled effect, making this an excellent option for those who love structured chaos. Whether for a casual day out or an evening ride, this look turns heads effortlessly.
6. Disheveled Medium-Length Waves
Medium-length messy waves offer a naturally stylish look with minimal effort. The movement and texture create an effortlessly cool vibe, ideal for men who prefer a rugged, free-spirited style. Whether styled with sea salt spray for added definition or left to air dry, this look is perfect for casual and adventurous settings alike. It’s an excellent choice for guys who embrace natural charm.
7. Messy Faux Hawk with Taper Fade
A messy faux hawk combines structure with an untamed aesthetic, making it a go-to for men who want an edgy yet stylish look. The height and texture add boldness, while the tapered sides keep it clean and modern. A bit of styling clay enhances the disheveled effect, giving it a natural hold. It’s a perfect hairstyle for a night out or an effortlessly cool streetwear vibe.
8. Wild Curls with a Natural Flow
Embracing natural curls in a messy style creates an easygoing yet fashionable aesthetic. The unstructured nature of the curls adds personality and movement, making it ideal for men who prefer a low-maintenance but stylish look. A lightweight curl-enhancing cream helps define the shape while keeping the bounce intact. This hairstyle is perfect for those who want to highlight their natural texture without over-styling.
9. Messy Spiky Hair with a Rugged Edge
Spiky hair with a messy finish is a great choice for those who want an edgy, rebellious style. The disheveled spikes create a sense of movement, while a matte styling product helps maintain volume without stiffness. This rugged, effortless hairstyle pairs well with a casual, laid-back outfit, making it ideal for men who want a bold, adventurous look that’s easy to maintain.
10. Messy Bedhead Look with a Carefree Vibe
The messy bedhead look is perfect for men who prefer a stylishly unkempt appearance. With soft waves and natural volume, this hairstyle exudes effortless charm. A bit of texturizing spray can enhance the look while keeping it touchable and flexible. It’s an excellent choice for those who want a casual, easygoing hairstyle that still looks put together without requiring much effort.
11. Layered Messy Mop Top
The layered mop-top is a trendy and easy-to-style option for men who want a relaxed yet fashionable look. The choppy layers add texture and depth, making it ideal for a carefree, tousled appearance. A light styling cream can help maintain the messy effect without making it look too structured. This hairstyle works well for casual days out and gives off a cool, effortless vibe.
12. Messy Side Part with Soft Volume
A messy side part strikes the perfect balance between sophistication and relaxed charm. The natural volume and slightly tousled strands make it versatile for both casual and formal settings. A light pomade can enhance texture while keeping it flexible. This look is ideal for men who want a refined hairstyle that still maintains a laid-back, approachable feel.
13. Windswept Messy Hair with a Beachy Vibe
The windswept, beachy look is a perfect choice for men who love an effortless, sun-kissed style. The tousled waves create a relaxed, adventurous appearance, ideal for both city life and vacations. A bit of sea salt spray enhances texture and gives a naturally voluminous finish. This hairstyle embodies a free-spirited, confident energy that suits any casual setting.
14. Messy Textured Pompadour
A messy pompadour blends vintage style with modern texture, creating a bold yet relaxed aesthetic. The voluminous top adds height, while the tousled waves keep it casual and easygoing. A lightweight wax or mousse can help maintain the shape while keeping the look natural. This hairstyle is perfect for men who want to channel a cool, effortless charm with a hint of retro flair.
15. Messy Slicked-Back Hair with a Modern Edge
The messy slicked-back look is a modern take on a classic hairstyle, offering a perfect blend of sophistication and effortless charm. The slight tousle adds personality, making it less rigid and more relaxed. A light hold styling cream enhances the natural texture while keeping it in place. This hairstyle is perfect for men who want a polished yet carefree appearance that works for both casual and formal settings.
16. Curly Messy Undercut
A curly messy undercut is a great way to embrace natural curls while keeping the sides sharp and clean. The contrast between the voluminous top and faded sides makes this look stylish and easy to maintain. A curl-enhancing cream or light mousse adds definition without weighing the curls down. This hairstyle is perfect for men who want a trendy, effortless look with a touch of uniqueness.
17. Messy French Crop with Choppy Layers
The messy French crop is a low-maintenance yet stylish option that suits a variety of face shapes. The choppy layers add dimension and movement, making it appear effortlessly cool. A small amount of matte pomade or wax helps maintain the texture while keeping the look relaxed. This hairstyle is ideal for those who want a short, fashionable cut without too much styling effort.
18. Disheveled Ivy League Cut
The disheveled Ivy League cut takes a traditionally polished hairstyle and gives it a casual, modern twist. The slightly messy top adds volume and movement, making it versatile for both professional and relaxed settings. A light touch of styling mousse or wax keeps it flexible without looking overly styled. This look is perfect for men who want a refined yet approachable hairstyle.
19. Messy Tapered Waves with a Soft Flow
Messy tapered waves offer a relaxed yet sophisticated look that works well for various occasions. The contrast between the short sides and the voluminous top creates a modern silhouette, while the soft waves add movement. A lightweight styling cream helps enhance the natural texture without making it stiff. This hairstyle is perfect for men who want a stylish but laid-back appearance.
20. Choppy Messy Fringe with a Playful Edge
A choppy, messy fringe is perfect for men who want a fun, youthful hairstyle with an effortless touch. The irregular layers add dimension, making it appear more natural and relaxed. A small amount of styling paste can enhance the tousled effect without making it too structured. This look is great for those who want a casual, slightly edgy style that requires minimal maintenance.
21. Messy Faux Undercut with Natural Flow
A faux undercut offers the stylish appeal of an undercut without the commitment of shaving the sides. The messy, voluminous top adds movement and character, while the slicked-back sides provide a sharp contrast. A lightweight styling cream or mousse helps maintain the shape while keeping it flexible. This look is great for men who want an edgy, fashionable style with a relaxed feel.
22. Messy Shaggy Layers with a Retro Vibe
A shaggy, messy layered cut offers a retro-inspired look with modern appeal. The natural waves and unstructured layers create a dynamic, effortless style that suits different hair textures. A bit of texturizing spray helps enhance the movement while keeping the style manageable. This is the perfect hairstyle for men who love a relaxed, rockstar-inspired aesthetic.
23. Undone Messy Bun with Loose Strands
A messy bun is a simple yet stylish way to keep long hair out of the face while maintaining a laid-back look. The loose strands add a touch of effortless charm, making it ideal for both casual and semi-formal settings. A bit of lightweight styling cream helps tame flyaways without losing the natural flow. This hairstyle is perfect for men who embrace a relaxed, bohemian-inspired style.
24. Casual Messy Side-Swept Hair
Side-swept messy hair is a timeless choice that exudes effortless cool. The slightly tousled finish adds personality, making it look stylish without trying too hard. A light styling wax helps keep the shape intact while maintaining a natural, touchable feel. This look works well for any occasion, making it a go-to option for men who want a low-maintenance yet fashionable hairstyle.
Conclusion
Messy hairstyles are perfect for guys who want a laid-back yet stylish look. Whether you prefer short, medium, or long hair, there’s a messy style that suits you. These hairstyles add character and an easygoing charm to your overall appearance. With the right styling products and minimal effort, you can achieve a fashionable, effortless look.
