25 Messy Medium Hairstyles That Look Undone but Not Unkempt

There is a real difference between hair that looks relaxed and hair that looks like you gave up. The gap between them is usually texture and where the loose pieces fall. Hair that has been styled and then loosened reads as deliberate. Hair that was never styled at all mostly reads as flat. Shoulder length is the ideal canvas for this, since there is enough to twist and pin but not so much that a bun becomes heavy. Almost everything below works better on second-day hair, which is the one piece of advice worth taking seriously.

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Undone Collarbone Waves

Loose waves falling to the collarbone with slightly uneven ends and no obvious pattern.

The unevenness is what sells it. Waves that fall in matching rows look set rather than natural.

Great for anyone who wants something that looks like it happened on its own. Break up the waves with your fingers once they cool, and skip the brush entirely.

Off-Centre Part With Uneven Waves

Shifting the part slightly off the middle so one side carries more hair than the other.

The asymmetry creates volume on the heavier side and lets the two sides fall differently, which reads as relaxed rather than arranged.

Perfect for a fast change with no tools. Set the part while the hair is damp so it holds, and let the lighter side tuck behind your ear if it wants to.

Bedhead Texture Spray Finish

Texture spray misted through dry hair from the mid-lengths down, then scrunched upward with your hands.

The spray roughs up the surface slightly, which is what gives the hair grip and stops it hanging smooth.

Works especially well on straight hair that has no natural movement. See our straight medium hairstyles post for the smooth versions if you want a contrast.

Second-Day Refresh With Dry Shampoo

Dry shampoo worked into the roots on unwashed hair, then the lengths reshaped by hand.

Clean hair is slippery and holds nothing. Day two hair has the grip that every style below depends on.

Great for stretching your wash schedule. Apply at the roots only, leave it a minute, then rub it in properly rather than brushing it through.

Rough Air Dry

Hair left to dry with no dryer and no product, ruffled occasionally with your fingers while it goes.

The disturbance while drying is what creates the irregular texture. Hair left completely still dries flat.

Suits anyone with some natural bend. Our wavy medium hairstyles post covers how to get more from natural texture if this is your starting point.

Finger-Dried Tousled Blowout

A dryer used with no brush at all, hair lifted and scrunched with your fingers as it dries.

Skipping the brush means nothing gets smoothed into place, so the volume stays irregular.

Perfect for building body without the neatness of a proper blowout. Keep the dryer moving and aim it at the roots, tipping your head from side to side as you go.

Grown-Out Bangs Pushed Aside

Bangs at that awkward length, pushed to one side and left to fall where they land.

Rather than fighting the growing-out stage, this leans into it, and the pieces falling across the forehead add to the relaxed effect.

Great for anyone stuck between a fringe and no fringe. A little cream on your fingertips keeps them separated instead of sitting as one flat block.

Messy High Bun

Everything gathered high on the crown, twisted loosely and pinned without smoothing anything down.

Height at the crown is doing a lot of the work here, and the loose pieces around the hairline stop it looking severe.

Suits almost every occasion. Spray dry hair with hairspray before you gather, which is the step most people skip and the reason their bun collapses.

Textured Low Bun

A bun sitting at the nape, teased slightly at the crown first, with sections wrapped loosely rather than pulled tight.

Teasing before you gather gives the finished bun volume that a tight low bun never has.

Works especially well on round and heart-shaped faces, since the crown lift adds a bit of height. Dry shampoo or salt spray beforehand makes it far easier to hold.

Twisted Low Bun

The whole length twisted from root to ends, then coiled at the nape and pinned without tightening.

The twist creates visible texture through the bun itself, so it catches light instead of sitting as a smooth ball.

Perfect for medium length specifically. There is enough hair to form a proper coil without the weight pulling it loose by lunchtime.

Claw Clip French Twist

Hair rolled upward against the back of the head and secured with a claw clip instead of pins.

It takes about fifteen seconds, which is the entire appeal, and the clip holds better than pins on medium length.

Great for straight to softly wavy hair. Pull a few pieces loose at the crown and around the ears afterward, since the roll itself comes out quite neat.

Half-Up Messy Bun

The top section gathered into a small loose bun with the rest of the length left down.

You get your hair off your face without committing to a full updo, and the length still shows.

Suits anyone whose hair is not quite long enough for a full bun. Our easy medium hairstyles post has more quick options along these lines.

Curly Chignon

Curls or waves gathered low at the nape and pinned into a soft shape, with the curl pattern left visible throughout.

Curly hair does most of the work here, since the texture creates the volume and irregularity you would otherwise have to build.

Great for anyone with natural curl. See our curly medium hairstyles post for cuts that make this easier to pull off.

Looped Bun

The ponytail folded back through the elastic in a loop, leaving the ends sticking out rather than tucked away.

Loose ends are what make the shape look relaxed. Tucking them creates something much more formal.

Perfect for medium length, which is often too short to tuck neatly anyway. Two or three loops give you more fullness than one.

Teased Crown Bouffant Updo

Serious volume built at the crown by teasing, with the rest gathered up and pinned behind it.

Big volume on top with loose texture through the back is a specific look, and it needs the teasing to hold.

Works especially well for evening events. Backcomb in small sections at the crown, then smooth just the surface over so the teasing does not show through.

Pinned Curls Updo

All the hair curled first, then pinned up in no particular arrangement.

Because the curls create their own structure, the pinning does not need to be neat or planned.

Great for weddings and formal evenings. Our medium hairstyles for weddings post covers more variations. Curl everything, tease the crown lightly, then pin without overthinking the placement.

Messy High Ponytail

A high ponytail with the front sections left slightly loose and pieces pulled out around the face.

Clipping the front pieces away before you gather, then releasing them afterward, gives you a much better result than trying to pull them out at the end.

Suits busy mornings. Tug gently on the crown after tying to lift it, which stops the ponytail looking pulled flat against the head.

Low Undone Ponytail With Twists

Hair gathered low at the nape with the side sections twisted loosely before joining the tie.

The twists give the sides some shape, so the style has detail without needing pins or braiding.

Perfect for work days when you want something more than a plain ponytail. Loosen the twists slightly after securing so they sit soft rather than tight.

Pulled-Apart Dutch Braid

A Dutch braid worked with relaxed tension, then each section tugged outward once it is finished.

Pulling the sections apart afterward is the technique. Braiding loosely from the start just makes the braid fall out.

Great for medium length, where a braid stays manageable. Flyaways along the parting are part of the look, so leave them alone.

Boho Braid With Flyaways

A loose braid with face-framing pieces deliberately left out at the front.

Leaving the front sections free keeps the style soft around the face, which is what separates a relaxed braid from a schoolgirl one.

Suits anyone who wants something quick but detailed. Our medium hairstyles for school post has more braided options if you need everyday variations.

Fishtail Chignon

A fishtail braid formed first, then coiled at the nape and pinned into a bun shape.

The woven pattern creates the impression of far more hair than there is, which suits medium length well.

Works especially well for formal events. Pull the braid apart gently before you coil it, since a tight fishtail looks stiff once it is pinned.

Half-Up Braid

A single braid taken from the top section and secured at the back, with the rest of the length loose.

The braid handles the front while the length stays visible, and it holds better than a plain half-up on fine hair.

Great for anyone who wants detail without an updo. Our medium hairstyles for thin hair post covers making half-up styles look fuller.

Loosened Crown Braid

A braid running around the head like a band, pinned in place and then pulled looser once it is secured.

Loosening afterward gives it width and softness. Left tight it looks like something set for a costume.

Perfect for keeping everything off your face on hot days. Medium length usually needs two braids meeting at the back rather than one going all the way around.

Half-Up Twist With Tendrils

Two sections from the sides twisted back and pinned together, with short pieces left loose around the face.

The tendrils are the whole point. Pulled fully back it becomes a different, much neater style.

Suits anyone who wants their hair handled at the front only. Twist rather than simply sweeping back, since the twist holds far better through the day.

Clipped-Back Sides With Volume on Top

Both sides pinned or clipped back behind the ears while the crown stays lifted and full.

Keeping height on top while clearing the sides gives you shape without needing an updo.

Great for a quick reset when your hair is not cooperating. Tease the crown lightly first, then clip the sides back, and our short hair updos post covers the same idea on shorter lengths.