Exploring 31 Trendy Messy Haircut Men Styles for Short Medium and Long Hair


In today’s fashion landscape, the polished, slicked-back look has given way to something more relaxed and effortless: the messy haircut. This style is not just about looking unkempt but about embracing a more natural and spontaneous hair aesthetic that suits a variety of occasions and face shapes. From casual days at the coffee shop to formal events, a well-styled messy haircut can truly make a statement. This article explores ten diverse messy hairstyles that cater to different hair types and lengths, demonstrating the versatility and appeal of this laid-back trend.

Windswept Waves for Medium Length Hair

Medium lengths of hair offer the perfect canvas for the wavy, windswept look, ideal for creating an aesthetic appeal that feels both spontaneous and controlled. This style works best for oval and heart-shaped faces, complementing soft features with its dynamic motion. Eye colors like hazel or green are particularly accentuated by the golden or ash-blonde hues often associated with this style.

In terms of styling, achieving this look involves a light touch with a sea salt spray and a diffuser to enhance the natural waves. Maintenance is straightforward with a moisturizing conditioner to prevent frizz and maintain the hair’s health and texture.

The Textured Top with Mid Fade

Perfect for short to medium hair, the textured top combined with a mid fade makes a sharp statement. This cut is best suited for square and angular faces as it softens the jawline while adding height on top. The style is versatile, fitting both professional environments and casual outings.

To get this style, ask your barber for a textured cut on top with graded scissors work. Style it with a matte pomade to give hold and volume without the shine. Regular trims every few weeks will keep the fade sharp and the texture pronounced. Using a daily volumizing shampoo can help maintain the volume and texture needed for this style.

Korean Tousled Bob

The Korean tousled bob is a testament to how asian hairstyles have permeated western fashion, offering a chic and effortless look ideal for straight hair. This style is particularly flattering for round and diamond face shapes, enhancing the facial structure with its voluminous layers.

Styling involves blow-drying with a round brush to add volume and a bit of curling at the ends for that perfect tousle. To maintain the look, a light hold hairspray and regular trims are essential to keep the bob in shape. For hair care, opt for a smoothing shampoo to keep the hair silky and manageable.

Effortless Long Curls

Long, curly hair can beautifully pull off a messy look that exudes elegance and personality. Ideal for oblong and oval faces, this style highlights the natural volume and texture of curly hair.

Achieve this by using a curl-enhancing cream and drying with a diffuser to avoid frizz. For maintenance, a curl-specific conditioner and occasional deep conditioning treatments will keep the curls bouncy and healthy.

Short and Choppy Layered Crop

A short, choppy layered crop is an excellent option for adding texture and edge to shorter hair. Suitable for all face shapes, this versatile cut can adapt to both subtle and bold personal styles.

Styling this cut requires minimal effort with a texturizing paste to mold the layers and add separation. Maintain the sharpness of the cut with regular monthly trims and wash with a volumizing shampoo to keep the hair full and lively.

Classic Bedhead

The classic bedhead look is perennially popular, bringing a rugged but appealing aesthetic to medium-length hair. This style suits almost every face shape and gives a youthful, carefree vibe that’s hard to beat.

Style it by working some texturizing mousse through damp hair and then air-drying. To maintain, use a light shampoo and occasionally treat your hair to a hydrating mask to keep it looking healthy and styled without effort.

Surf’s Up Wavy Shag

The surf-inspired wavy shag is perfect for those who prefer a longer, low fade cut that meshes well with a laid-back lifestyle. This look is ideal for round and heart-shaped faces, enhancing facial features with its layered texture.

A salt spray and light scrunching are key to enhancing the natural wave, while a weekly use of a nourishing conditioner will help maintain hair health and texture.

Disheveled Pixie Cut

A disheveled pixie cut offers a bold and stylish look that works wonderfully on short hair. This cut is particularly flattering for triangular and heart-shaped faces, focusing attention upward and balancing facial proportions.

Styling is simple with a dab of styling cream for texture and hold. Keeping this style pristine involves regular trims and using a strengthening shampoo to keep the hair healthy.

Rugged Taper with Defined Waves

A rugged taper cut combined with defined waves offers a structured yet casual look. Ideal for medium to long hair, this style works best for oval and square faces, providing balance and texture.

Use a lightweight mousse to define the waves and a medium hold gel to maintain the shape throughout the day. Regular conditioning and the occasional use of a deep conditioning mask will keep the waves smooth and defined.

Bohemian Long Locks

Bohemian long locks are perfect for those who wish to sport long, flowing hair with a touch of wildness. This style is ideal for all face shapes and is especially appealing with lighter eye colors like blue or green.

Style with a minimal touch, using a curl enhancer for natural waves and a leave-in conditioner to maintain softness and manageability. Regular trims and avoiding overwashing will help maintain the natural oils that enhance this style’s appeal.

Wind-Tossed Fringe

The Wind-Tossed Fringe is a dynamic choice for those with short to medium hair lengths. This cut works particularly well for those with a square face, as it softens the facial angles while the movement in the fringe draws attention to the eyes, particularly enhancing lighter eye colors.

The style is achieved by cutting a textured fringe and using a lightweight gel to toss the hair casually forward. This look requires minimal upkeep, just a regular trim to maintain the length of the fringe and a daily touch-up with gel to keep it looking fresh and lively.

Urban Messy Quiff

The Urban Messy Quiff modernizes a classic look, suitable for medium hair and adaptable across various occasions. It fits round and oval face shapes, offering height and volume that elongate the face subtly.

To style, use a volumizing mousse and blow-dry the hair upwards and back for that quintessential lift at the front. Maintain the volume and health of your quiff with a volumizing shampoo and perhaps a light spray of sea salt for added texture.

Spiky Disarray

Ideal for those who prefer a bold look, the Spiky Disarray suits short hair and creates a standout, edgy aesthetic. This style works best with angular or oval faces, emphasizing strong facial features.

Achieve this look with a high-hold gel, working the product into damp hair and pulling sections up and out for a spiked effect. Keep your spikes sharp with frequent trims and use a clarifying shampoo to remove product build-up.

Casual Tousled Top

A Casual Tousled Top is perfect for medium lengths of hair, giving a relaxed yet stylish vibe suitable for both casual and formal settings. It’s particularly flattering for heart and round face shapes, balancing the face with its voluminous top.

Styling involves a light pomade or wax to add texture and volume by hand-tousling. A daily lightweight conditioner will help maintain the natural look and feel of the hair without weighing it down.

Slicked-Back Waves

Slicked-Back Waves bring a sophisticated edge to wavy, medium to long hair. This look is ideal for oval and rectangle face shapes, as it draws the hair away from the face, highlighting strong jawlines.

This style can be achieved with a strong-hold gel or pomade to keep the waves slicked back. To maintain the health of wavy hair, use a hydrating conditioner and occasional deep conditioning treatments to keep waves smooth and manageable.

Choppy Sea Salt Curls

For those with naturally curly or wavy hair, Choppy Sea Salt Curls offer a beach-inspired, carefree look. It’s great for all face shapes and gives a youthful, energetic appearance.

Apply sea salt spray to damp hair and let it air-dry, or use a diffuser to enhance the natural curls. Maintain the definition and health of curls with a curl-enhancing shampoo and conditioner, ensuring they stay bouncy and voluminous.

Refined Bedhead Pomp

The Refined Bedhead Pomp is a classy version of the messy style, fitting for straight or wavy medium hair. Suitable for round and square faces, it adds height and structure, enhancing the facial features.

Style with a lightweight wax, pushing the hair back and up while allowing some strands to fall naturally for that refined, yet slightly disheveled look. Use a nourishing shampoo to keep hair healthy and a touch of hairspray to hold the style in place throughout the day.

Layered Shag with Curtain Bangs

The Layered Shag with Curtain Bangs is an excellent choice for medium to long hair, giving a rockstar vibe that suits oval and heart-shaped faces. This cut is perfect for those looking to add volume and texture.

Styling involves blow-drying with a round brush and applying a texturizing spray for that perfect tousled finish. To maintain the look, opt for a volumizing shampoo and regular trims to keep the layers defined.

Angular Fringe and Low Fade

The Angular Fringe and Low Fade combination offers a contemporary take on messy styles for straight and short hair. This hairstyle accentuates angular and oval face shapes, with the fringe creating a striking diagonal line across the face.

Style the fringe with a light pomade for hold and texture. Maintenance involves regular trims to keep the fade neat and the fringe sharp, along with a balancing shampoo to keep the scalp healthy.

Wild Tousled Locks

Wild Tousled Locks are all about embracing the natural texture of long hair. This style is particularly flattering for square and oval faces, as it softens and adds movement to the hair’s natural flow.

To achieve this, use a curl enhancer or mousse and scrunch the hair while air-drying. For maintenance, regular hydration with deep conditioners and a gentle shampoo will keep the locks healthy and vibrant.

Effortless Side-Swept Layers

The Effortless Side-Swept Layers hairstyle is perfect for men with medium to long hair, providing a graceful flow that suits particularly well with oval and oblong face shapes. This look softens the facial features and adds a romantic flair, especially when paired with light eye colors.

To style, use a lightweight styling cream to create definition and sweep the hair gently to one side. Maintain the hairstyle with regular trims every six to eight weeks and use a moisturizing shampoo to keep hair smooth and manageable.

Vintage Tousled Pompadour

The Vintage Tousled Pompadour revives classic style with a modern twist, ideal for short to medium hair. It works best on round and square faces by elongating the appearance and adding a touch of class.

Achieve this look with a volumizing mousse before blow-drying the hair upwards and back, then finish with a matte pomade to hold the volume while keeping the texture soft and touchable. To keep the pomp in prime condition, use a strengthening shampoo and don’t forget to condition regularly.

Textured Waves with Mid-Part

Textured Waves with Mid-Part cater to those with medium or long wavy hair, offering a relaxed yet stylish look that’s particularly flattering for heart and diamond-shaped faces. This style enhances the natural wave pattern while the mid-part frames the face symmetrically.

For styling, apply a sea salt spray to damp hair, part it down the middle, and let it air dry or use a diffuser. Maintain the hairstyle’s effortless vibe with a light-touch conditioner that won’t weigh down the waves, ensuring they stay defined and lively.

Disconnected Undercut with Rough Top

The Disconnected Undercut with Rough Top is an edgy option suitable for men with short to medium straight or wavy hair. The sharp contrast between the very short undercut and the textured top is ideal for highlighting angular features, suitable for triangular and rectangular face shapes.

Style this bold look by using a strong-hold wax to add texture to the top section, creating a rugged, tousled effect that stands out against the clean-cut sides. Maintenance requires frequent trims to keep the undercut sharp and a hydrating shampoo to keep the longer sections healthy and styled.


Messy hairstyles for men are all about embracing imperfection and personal style. Whether you’re looking for a low-maintenance daily look or something to make a statement at a special event, these ten hairstyles offer something for every man. Experiment with these styles and share your experiences or your own messy hair ideas in the comments below. Let’s keep the discussion flowing and help each other find the perfect messy look!

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