20 Effortlessly Cool Messy Hairstyles for Men

Messy hairstyles for men have become increasingly popular in recent years, offering a perfect blend of casual charm and stylish sophistication. These looks are all about embracing natural texture and creating an intentionally disheveled appearance that exudes confidence and effortless cool.

Whether you’re looking for a low-maintenance everyday style or a trendy look for special occasions, these 20 messy hairstyles for men are sure to inspire your next trip to the barber.

1. Tousled Quiff

The tousled quiff is a classic messy hairstyle that combines volume at the front with a textured, undone finish. To achieve this look, start with a short back and sides, leaving more length on top. Use a volumizing mousse or sea salt spray on damp hair, then blow-dry while lifting the hair at the roots with your fingers or a round brush. Once dry, use a small amount of matte pomade or clay to create piece-y texture and height at the front. Finish by tousling the hair with your fingers for that perfectly imperfect look.

2. Messy Undercut

The messy undercut features short, buzzed sides and back with longer, textured hair on top. This versatile style can be worn sleek and neat or deliberately disheveled for a more casual vibe. To style, apply a texturizing product to damp hair and blow-dry while tousling with your fingers. Once dry, use a small amount of matte paste or clay to enhance texture and separation. For added volume, try backcombing the top section gently before smoothing it over with your fingers.

3. Bedhead Crop

The bedhead crop is all about embracing your natural hair texture and creating a “just woke up like this” look. This style works best on shorter to medium-length hair with some natural wave or texture. To achieve this effortless look, apply a small amount of sea salt spray or texturizing cream to damp hair and allow it to air dry. Once dry, use your fingers to tousle and separate the hair, focusing on creating piece-y texture throughout. The key is to avoid over-styling – let your natural hair texture shine through.

4. Messy Fringe

A messy fringe adds a youthful, edgy touch to any hairstyle. This look works well with medium to long hair on top and can be combined with various lengths on the sides. To style, apply a volumizing mousse to damp hair and blow-dry while directing the fringe forward and to one side. Once dry, use a small amount of texturizing paste or clay to create separation and piece-y texture in the fringe. Finish by tousling the rest of the hair for a cohesive, messy look.

5. Textured Pompadour

The textured pompadour puts a modern, messy spin on a classic style. This look features shorter sides with longer hair on top, styled upward and back for height and volume. To achieve this style, apply a volumizing product to damp hair and blow-dry while lifting the hair at the roots. Once dry, use a matte pomade or clay to create texture and hold. Instead of smoothing the top section back neatly, use your fingers to tousle and separate the hair for a more undone finish.

6. Messy Man Bun

The messy man bun is a relaxed, effortless take on the popular long hairstyle. This look works best with hair that’s at least shoulder-length. To style, apply a small amount of texturizing cream or sea salt spray to damp hair and allow it to air dry for natural texture. Once dry, gather your hair at the crown of your head and secure it with an elastic band, leaving some strands loose around your face for a softer look. Don’t worry about making it too neat – the messier, the better.

7. Shaggy Layers

Shaggy layers offer a versatile, low-maintenance messy style that works well for various hair types and face shapes. This cut features multiple layers throughout the hair, creating natural movement and texture. To style, apply a volumizing mousse or sea salt spray to damp hair and either air dry or blow-dry with a diffuser attachment. Once dry, use a small amount of texturizing paste to enhance separation and piece-y texture throughout the layers.

8. Messy Faux Hawk

The messy faux hawk combines the edgy appeal of a mohawk with a more wearable, textured finish. This style features shorter sides with longer hair on top, styled upward and toward the center. To achieve this look, apply a strong-hold mousse or gel to damp hair and blow-dry while lifting the hair at the roots. Once dry, use a matte paste or clay to create texture and separation, focusing on styling the hair upward and toward the center. The key is to maintain some height while keeping the overall look tousled and undone.

9. Textured Slick Back

The textured slick back offers a modern, messy take on the classic slicked-back style. This look works well with medium to long hair on top and can be paired with various side lengths. To style, apply a sea salt spray or texturizing cream to damp hair and blow-dry while directing the hair backward. Once dry, use a matte pomade or clay to slick the hair back, but instead of smoothing it down completely, use your fingers to create texture and separation throughout.

10. Messy Curls

Embracing natural curls is a great way to achieve an effortlessly messy look. This style works best for men with naturally curly or wavy hair. To enhance your curls, apply a curl-defining cream or leave-in conditioner to damp hair and allow it to air dry or diffuse on low heat. Once dry, use your fingers to gently separate and fluff the curls for added volume and texture. Avoid using a brush or comb, as this can create frizz and disrupt the natural curl pattern.

11. Textured Caesar Cut

The textured Caesar cut is a modern, messy interpretation of the classic Roman-inspired style. This look features short, textured hair all over with a slightly longer fringe. To style, apply a small amount of texturizing paste or clay to damp hair and use your fingers to tousle and piece out the hair as it air dries. Once dry, add more product if needed to enhance texture and separation, focusing on creating a slightly messy fringe.

12. Messy Side Part

The messy side part combines the sophistication of a traditional side part with a more relaxed, textured finish. This versatile style works well with various hair lengths and types. To achieve this look, apply a volumizing mousse to damp hair and blow-dry while creating a deep side part. Once dry, use a matte pomade or clay to enhance texture and separation, focusing on tousling the hair on top and smoothing the sides slightly. The key is to maintain the side part while keeping the overall look deliberately disheveled.

13. Textured Crop

The textured crop is a low-maintenance, messy style that works well for men with straight or slightly wavy hair. This cut features short to medium length hair all over with textured ends for added movement. To style, apply a small amount of texturizing cream or paste to damp hair and either air dry or blow-dry with your fingers. Once dry, use a matte product to enhance texture and separation, focusing on creating piece-y definition throughout the hair.

14. Messy Spikes

Messy spikes offer a more relaxed, textured take on the classic spiky hairstyle. This look works best with short to medium length hair and can be adapted for various hair types. To style, apply a strong-hold mousse or gel to damp hair and blow-dry while lifting sections of hair with your fingers. Once dry, use a matte paste or clay to create defined, piece-y spikes throughout the hair. The key is to keep the spikes soft and tousled rather than stiff and uniform.

15. Tousled Mid-Length

The tousled mid-length style is perfect for men who want to grow out their hair while maintaining a stylish, messy look. This cut features hair that falls between the ears and shoulders with layers for added texture and movement. To style, apply a sea salt spray or texturizing cream to damp hair and allow it to air dry or diffuse on low heat. Once dry, use a small amount of matte pomade or clay to enhance texture and separation, focusing on creating a piece-y, windswept effect.

16. Messy Ivy League

The messy Ivy League puts a tousled spin on the classic preppy cut. This style features short sides with slightly longer hair on top, styled with a side part and textured finish. To achieve this look, apply a volumizing product to damp hair and blow-dry while creating a side part. Once dry, use a matte pomade or clay to tousle the hair on top, creating texture and separation while maintaining some semblance of the original Ivy League shape.

17. Textured French Crop

The textured French crop is a stylish, low-maintenance messy hairstyle that works well for various face shapes and hair types. This cut features short sides and back with a slightly longer fringe that’s texturized for a piece-y finish. To style, apply a small amount of texturizing paste or clay to damp hair and use your fingers to tousle and piece out the fringe as it air dries. Once dry, add more product if needed to enhance texture and separation throughout the top and fringe.

18. Messy Surfer Hair

Messy surfer hair embodies the laid-back, beachy vibe of sun-kissed locks. This style works best with medium to long hair and natural waves or texture. To achieve this look, apply a sea salt spray to damp hair and allow it to air dry or scrunch-dry with a diffuser. Once dry, use your fingers to tousle and separate the hair, focusing on creating a piece-y, windswept effect. The key is to embrace your hair’s natural texture and movement for that effortless, just-off-the-beach look.

19. Textured Buzz Cut

The textured buzz cut proves that even the shortest hairstyles can embrace a messy, textured finish. This style features a classic buzz cut with slightly more length on top for added texture. To style, apply a small amount of texturizing paste or clay to dry hair and use your fingers to create subtle texture and separation on top. The result is a low-maintenance yet stylish look that adds interest to the traditional buzz cut.

20. Messy Mohawk

The messy mohawk offers a more wearable, textured take on the punk-inspired style. This cut features shaved or very short sides with a longer strip of hair down the center of the head. To style, apply a strong-hold mousse or gel to damp hair and blow-dry while lifting the center section with your fingers or a round brush. Once dry, use a matte paste or clay to create texture and separation in the mohawk, focusing on a tousled, piece-y finish rather than a smooth, uniform shape.

In conclusion, these 20 effortlessly cool messy hairstyles for men offer a range of options for guys looking to embrace a more relaxed, textured look. From short and low-maintenance styles to longer, more dramatic cuts, there’s a messy hairstyle to suit every preference and hair type. The key to pulling off these looks is to embrace your natural hair texture, use the right products, and remember that imperfection is part of the charm. With a little practice and the right styling techniques, you’ll be rocking your chosen messy hairstyle with confidence in no time.

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