22 Medium Messy Curly Hairstyles for Men, Undone and Cool

Messy hair is a bit of a trick: the good kind looks undone but is actually deliberate. Curls give you a head start, since they are already textured, so a messy curly look on men comes together with barely any effort, but only if two things are right. The cut has to have enough layers and shape that the hair falls into place on its own, and you need the right product, a sea-salt spray or a matte paste, not a fistful of gel that turns messy-cool into crunchy. At medium length, curls have room to move without the commitment of long hair. Here are ways to wear that undone, textured look.

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Messy Curly Fringe

Pushed forward into a loose tousled fringe, a messy curly fringe keeps medium curls falling across the forehead with shorter sides. It has a relaxed, streetwear feeling and shows off your curl texture up front. Ask for choppy layers so it falls forward on its own, and use a sea-salt spray for that natural finish. Do not overthink it, since the mess is the point. Cool, casual, and youthful. The easygoing medium curly look for men.

Tousled Curls Worn Down

Tousled medium curls worn down and loose are about as easy as men's hair gets. Let the curls fall naturally to your ears or jaw with a rough part, and scrunch a little curl cream through so they stay defined rather than frizzy. Rough-dry with your fingers instead of a brush. The undone, lived-in finish is the whole appeal. Keep the ends moisturized so they do not dry out. Relaxed, textured, and low-effort. Medium curls at their most natural.

Messy Curly Quiff

Lifted up and back without being slicked, a messy curly quiff gives medium curls shape and attitude while staying undone. The height adds structure while the loose finish keeps it from looking stiff. Push the front up with a matte paste and leave it textured rather than perfect. Keep the sides tapered. It has energy and personality with minimal fuss. Bold, tousled, and cool. A messy take on a classic men's shape.

Messy Curly Flow

The messy bro flow lets medium curls sweep back off the face and fall where they will, undone and easygoing. It has a laid-back, surfer-meets-rockstar charm and works beautifully on curls, which give it built-in texture. Push the hair back while it dries, following the curl pattern, and finish with a light product. Pair it with stubble or a beard. Cool, relaxed, and low-maintenance. The classic undone medium curly look for men.

Medium Curly Shag

Bringing choppy feathered layers to your curls, a medium curly shag is full, messy, and rock-and-roll. The layers add movement and keep the curls from sitting as one heavy mass, and the shaggy shape thrives on undone texture. Rough-dry with a curl cream and let it fall naturally, since fussing over it defeats the point. Ask for plenty of layers. Textured, voluminous, and cool. A '70s-leaning messy cut that suits medium curls.

Messy Curly Mullet

Shorter on top and sides with a longer back, a messy curly mullet is worn undone and textured. The messy finish softens the mullet's bold shape and leans into its rebellious edge. A rough, choppy cut and a sea-salt spray give it that lived-in feel. It suits men who want real personality. Do not neaten it too much, since the mess is what makes it work. Edgy, current, and full of attitude.

Messy Side-Swept Curls

Messy side-swept curls push medium curls loosely to one side for a relaxed, off-center look. A deep, rough part sends the curls sweeping across, undone rather than combed. Work a little curl cream or paste through with your fingers and leave it textured. It frames the face while keeping that easy, thrown-together feel. Great for casual days and a laid-back vibe. Soft, cool, and low-effort. A simple way to wear medium curls with a bit of shape.

Curly Undercut With a Messy Top

Pairing short sides with a longer messy curly top, an undercut gives bold contrast. All the tousled curl stays up top while the sides are clipped short, keeping the width down. Wear the top loose, swept back, or falling forward, kept undone with a matte product. It needs regular cleanups on the sides. A strong, modern look for messy curls up top and sharpness at the sides. High-contrast and edgy.

Messy Curly Mop-Top

Full and round all over, a messy curly mop-top is a shaggy, retro, mop-like shape. It is unapologetically voluminous and undone, with the curls falling in every direction. Ask for a rounded, layered cut and style it with just a scrunch of cream, letting it do its own thing. Keep it moisturized so the volume stays soft. Fun, youthful, and full of texture. A carefree, big-curl look with personality.

Messy Curly Curtains

Messy curly curtains split medium curls down a rough middle part so they frame the face on each side, undone and textured. It is a soft, '90s-leaning look that works when your curls have enough length to sweep out. Part it loosely and let the curls fall where they will, scrunching in a little cream. Do not neaten it too much. Relaxed, retro, and cool. A messy way to wear the curtain look on curls.

Messy Curls With a Taper Fade

Cleaning up the sides while a messy top does its own thing, a taper fade with textured curls keeps things sharp at the edges. The fade makes the undone curls up top look intentional rather than unkempt, blending into the curl for a natural flow. Keep the top moisturized and defined with a curl cream, worn loose and messy. Refresh with water between washes. Clean at the sides, wild up top. A sharp, low-fuss medium curly look.

Textured Curls Swept Back

Textured medium curls swept back give a lived-in, athletic finish without slicking them flat. Push the curls back from your face with your fingers and a little light product, keeping the texture and movement visible rather than gelled down. It reads relaxed and masculine, especially with stubble or a short beard. Do not use a heavy gel, since the point is the texture. Cool, easy, and undone. A pushed-back medium curly look with plenty of movement.

Messy Curly Half-Up Bun

Tying the top back into a small loose bun, a messy half-up keeps the front of your medium curls out of your face while the rest hangs undone. It shows off the length and texture below. Leave it a little messy and pull a few curls loose. It suits medium curls with enough length to gather. Quick, casual, and cool. A practical, undone way to wear medium curls half up.

Messy Curls With a Headband

Holding messy medium curls back with almost no effort, a thin headband sits an inch back from your hairline while the curls fall loose behind it. It handles a workout or a hot day and adds a bit of cool without any styling. Refresh the curls with water first. Sporty, relaxed, and functional. A simple fix for messy medium curls on the go.

Messy Curls With a Bandana

Tied around the head, a rolled bandana gives messy medium curls a rugged, streetwise edge. Fold it into a band across your forehead, letting the textured curls fall loose behind. It holds the hair back, soaks up sweat, and adds attitude, pairing well with a beard. A classic black or paisley one suits it best. Casual, cool, and full of character. A functional accessory for undone medium curls.

Bed-Head Curls

Bed-head curls lean all the way into the just-woke-up look, medium curls left tousled and undone on purpose. Rough-dry your hair, scrunch in a little sea-salt spray or texture paste, and mess it up with your fingers, aiming for cool rather than neat. The trick is a bit of product so it looks deliberate, not flat and frizzy. Relaxed, careless, and youthful. The most undone medium curly look there is, done right.

Messy Curly Wolf Cut

Part shag and part mullet, a curly wolf cut gives medium curls heavy layers and disconnected, textured ends for a wild, messy shape. The built-in volume and rough layering make it look undone with almost no styling. It suits thick curls that need the bulk broken up. Diffuse or air-dry and leave it messy. Cool, edgy, and full of personality. A bold, textured cut for loud medium curls.

Messy Medium Afro

Worn full and undone, a messy medium afro keeps natural coils picked out into a loose, rounded shape rather than a neat, sculpted one. It celebrates the texture with a lived-in feel. Keep it moisturized with a leave-in daily, since dry coils lose their softness, and pick it out gently without over-neatening. An edge-up keeps the hairline clean. Bold, natural, and easygoing. A relaxed take on a medium afro.

Messy Twist-Out

Defined but undone, a messy twist-out gives you curls by twisting your natural hair, letting it set, and fluffing it out loosely. At medium length, the stretched curls look full and textured rather than perfectly uniform. Two-strand twist damp, moisturized hair, let it dry, then unravel and rough it up with your fingers. Keep it hydrated so the curls stay soft. Defined, voluminous, and undone. A relaxed medium twist-out.

Messy Medium Twists

Protective and relaxed, medium twists worn a little undone sit naturally rather than perfectly neat. Two-strand twist your coils to medium length for a lived-in feel. Moisturize with a leave-in before twisting, and keep the scalp cared for. Do not install them too tight at the roots. Best on 4A to 4C coils. Protective, defined, and easygoing. An undone take on medium twists.

Messy Curls With a Beard

Pairing messy medium curls with a beard is a rugged, balanced look. The beard grounds the tousled curls up top and adds structure to the face, so the mess reads intentional rather than unkempt. Keep both moisturized and roughly shaped, since curls and beards both frizz. Sweep the curls loosely to balance the beard. Masculine, rugged, and cohesive. The classic messy-curls-and-beard combination for medium length.

Colored Messy Curls

Color adds dimension to messy medium curls, since the texture and movement catch highlights beautifully. Subtle highlights or a lived-in balayage make the undone curls look richer and more dynamic. The honest caveat is that lightening curly hair can loosen the pattern and dry it out, so keep the lift gentle and deep-condition often. Deposit-only or darker shades are kinder to your curls. Rich, dimensional, and cool. Color that plays up messy curly texture.

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