Let's be honest - there's something incredibly appealing about that perfectly imperfect look, right? Messy hairstyles for men have completely taken over the style scene, and for good reason.
They're effortlessly cool, surprisingly versatile, and (best part) they actually look BETTER when you don't try too hard.
As someone who's experimented with everything from the slicked-back corporate look to the "I just rolled out of bed but somehow look amazing" vibe, I can tell you that embracing the mess might be the best hair decision you'll ever make.
Ready to ditch the perfectly combed look and embrace some stylish chaos? I've put together 20 of the absolute best messy hairstyles that'll work for different hair types, face shapes, and personal styles. Whether you're looking for something subtle for the office or want to go full rock star on the weekends, I've got you covered!
1. The Textured Crop
Ever noticed how some guys seem to have that perfect "messy on purpose" look that somehow still looks professional? That's the textured crop working its magic. This style keeps things short on the sides while leaving enough length on top to create texture and movement.
The beauty of this cut is in its versatility. You can wear it slightly neater for work and then mess it up with your fingers for after-hours. All you need is a small amount of matte paste or clay worked through dry hair, focusing on creating piece-y definition rather than uniform structure.
Pro tip: Ask your barber for a disconnected cut with texture on top. The contrast between the shorter sides and the textured top creates that perfect "I tried, but not too hard" aesthetic.
2. Messy Quiff
The quiff has been around forever, but the messy version takes this classic to new heights (literally). Unlike its more structured cousin, the messy quiff embraces natural movement and doesn't require military-grade precision to look good.
To nail this look, you'll need some length on top - around 3-4 inches is ideal. The sides can be anything from a subtle taper to a skin fade, depending on how dramatic you want the contrast to be. The key is creating height at the front while allowing the rest to fall naturally.
Styling secret: Blow dry your hair forward first, then backward to create volume, and finish with a texturizing product. Remember - the less perfect it looks, the better!
3. Bedhead Brilliance
Ever woken up, looked in the mirror, and thought "damn, my hair actually looks good right now"? That's the exact vibe we're going for with the bedhead style. It's probably the most effortless look on this list, but paradoxically, it might take a bit of work to perfect (isn't that always the way? :))
This style works best with medium-length hair that has some natural texture. The cut should have layers to enhance movement and prevent the hair from looking too heavy or flat.
How to achieve it: Apply a sea salt spray to damp hair, scrunch it up with your hands, and either air dry or use a diffuser on low heat. The less you touch it while drying, the better the natural texture will develop.
4. The Messy Man Bun
The man bun got a bad rap for a while (thanks, hipster overkill), but the messy version has breathed new life into this longer style. Unlike the sleek, tight man bun, the messy version embraces loose strands and imperfection.
This style obviously requires longer hair - you'll need at least enough length to pull back into a small bun or ponytail. The key difference is that you're not trying to capture every strand - some pieces should fall around your face or at the nape of your neck.
Style it right: Gather your hair loosely at the crown or back of your head, twist it once, and secure with a hair tie. Then gently pull out a few strands around your face and ears. The less perfect, the more stylish it looks.
5. Tousled Medium Length
This is my personal go-to when I'm growing out a shorter cut. The tousled medium length is that sweet spot between short and long hair where you've got enough to play with but not so much that it becomes high maintenance.
For this style, you want hair that hits somewhere between your ears and the base of your neck, with layers throughout to create movement. The cut should have texture built in, so ask your barber to point-cut or razor the ends rather than creating blunt lines.
Daily styling: Work a small amount of lightweight styling cream through damp hair, then either air dry or rough-dry with a blow dryer. Once dry, use your fingers to piece it out and create definition. No brush needed - ever!
6. Messy Pompadour
Think of this as the rebellious younger brother of the classic pompadour. While the traditional style is all about smooth, sleek perfection, the messy pompadour keeps the height and drama but adds texture and movement that feels modern and effortless.
You'll need significant length on top - at least 3-5 inches - with shorter sides for contrast. The key difference from a regular pomp is that you're not trying to create a uniform shape; instead, you want pieces going in slightly different directions.
Get it right: Use a blow dryer and round brush to create height at the roots, then mess up the smooth finish with your fingers and a texturizing product. The front should have the most height, gradually becoming less structured toward the back.
7. Curly Mess
Guys with natural curls or waves - this one's for you! For too long, men with textured hair were told to fight their natural pattern. Now? Those curls are your secret weapon for achieving the perfect messy look with minimal effort.
The key to this style is getting a cut that works with your natural texture rather than against it. You want enough length to allow the curls to form (usually at least 1-2 inches), with layers that enhance rather than weigh down your natural pattern.
Curl care: Invest in products specifically formulated for curly hair - a good curl cream or light gel will define your texture without the crunch. Apply to damp hair, scrunch gently, and either air dry or use a diffuser attachment on low heat.
8. Disheveled Side Part
The side part is traditionally one of the most "proper" men's hairstyles, but mess it up a bit and you've got something that works for both the boardroom and the bar. This style maintains the sophistication of a side part but adds texture and movement that feels contemporary.
Ask for a cut that's longer on top (around 2-3 inches) with a gradual fade on the sides. The key difference from a classic side part is that you don't want the part to be too precise or the hair too flat.
Daily styling: Create a rough part with your fingers rather than a comb, then use a matte product to add texture and separation. The goal is structure with movement - not slick perfection.
9. Messy Faux Hawk
Remember the super-gelled, perfectly pointed faux hawks of the early 2000s? Yeah, we're not doing that. The modern messy faux hawk keeps the general shape (longer in the center, shorter on the sides) but ditches the stiff, spiky finish for something much more touchable.
For this style, you want the hair on top to be around 2-3 inches long, with gradually shorter sides. Unlike the traditional faux hawk, the transition should be less dramatic and more blended.
Style it: Work a texturizing product through dry hair, using your fingers to push the center section up and back. The key is creating height without stiffness - you should be able to run your hands through it without destroying the style.
10. Shaggy Layers
Channel your inner 70s rock star with this longer, layered look that's making a major comeback. The modern shag is all about embracing natural texture and movement with layers that create volume and dimension.
This style works with medium to longer hair (usually past the ears) and looks best when cut with lots of layers throughout. The layers should be shorter around the crown and gradually longer toward the ends.
Make it work: Enhance your natural texture with a salt spray or light mousse, then either air dry or rough-dry with a blow dryer. The beauty of this cut is that it actually looks better slightly "lived in" - so the second or third day after washing might be when it looks its best!
11. Textured French Crop
Think of this as the cooler, messier version of the Caesar cut. The French crop keeps things short and manageable but adds texture on top for interest and movement.
This style features a short fringe (bangs) that sits just above the eyebrows, with the rest of the hair on top kept at a similar length. The sides are typically faded or tapered shorter. What makes it "messy" is the textured finish on top rather than a smooth, flat look.
Perfect for: Guys who want a low-maintenance style that still has personality. It's also great if you're starting to thin on top, as the textured finish creates the illusion of fuller hair.
12. Messy Undercut
The undercut has been dominating men's style for years now, but the messy version feels fresh and modern. Instead of slicking the top straight back, this style embraces natural movement and texture.
You'll need a significant contrast between the top and sides - typically the sides are buzzed very short (a #1 or #2 guard) while the top is left at least 3-4 inches long. The disconnection between the two should be dramatic and visible.
Daily wear: Apply product to damp hair and rough-dry for maximum volume. Once dry, use your fingers to create piece-y texture rather than a uniform direction. The contrast between the neat sides and the messy top is what makes this style work.
13. Wavy Mid-Length
Guys with natural waves, you've hit the genetic jackpot when it comes to messy styles! This mid-length cut embraces natural wave patterns for a look that's effortlessly cool.
For this style, you want hair that hits around the nape of the neck or collar, with layers throughout to enhance your natural wave pattern. The cut should work with your hair's natural tendency rather than fighting against it.
Wave enhancer: Apply a curl-enhancing cream to damp hair, scrunch gently, and let air dry whenever possible. Avoid touching your hair too much while it's drying to prevent frizz.
14. Messy Spikes
No, we're not talking about the rock-solid, gel-heavy spikes of the 90s. Modern messy spikes are softer, more natural, and definitely touchable. Think texture and dimension rather than sharp points.
This style works best with shorter to medium-length hair on top (1-3 inches) and shorter sides. The key is creating separation between pieces without making them look too uniform or deliberate.
Get the look: Work a small amount of matte paste or clay between your palms, then use your fingertips to create separation and lift at the roots. The spikes should go in slightly different directions for that perfectly imperfect finish.
15. Disheveled Ivy League
The Ivy League (or Harvard Clip) is traditionally a very neat, conservative cut. But mess it up a bit, and you've got something that maintains that classic appeal while feeling much more modern and relaxed.
This style keeps the general shape of the Ivy League - short on the sides and back, slightly longer on top with enough length to part - but adds texture and movement to the traditionally flat top section.
Modern twist: Instead of using a comb and pomade for a sleek finish, use your fingers and a matte product to create a more natural, textured look. The part should be visible but not razor-sharp.
16. Messy Fringe
Fringes (or bangs) aren't just for emo kids anymore. A textured, piece-y fringe that falls just above or slightly over the eyebrows can add instant style to almost any face shape.
For this look, you want the front section to be long enough to reach your eyebrows, with the rest of the top slightly shorter. The sides can be anything from a subtle taper to a dramatic undercut, depending on your preference.
Styling tip: Apply product to damp hair, then blow dry the fringe using your fingers to direct it. The key is creating separation between pieces rather than a solid curtain of hair across your forehead.
17. Tousled Surfer
Channel those laid-back beach vibes with this longer style that looks like you just stepped off your surfboard (even if the closest you get to surfing is watching Point Break). This cut embraces natural texture and movement for an effortlessly cool vibe.
You'll need medium to longer hair for this one - typically past the ears and possibly touching the shoulders. Layers throughout are essential to prevent the hair from looking too heavy or flat.
Beach vibes: Sea salt spray is your best friend for this style. Spray generously on damp hair, scrunch with your hands, and let air dry whenever possible. The less you fuss with it, the more authentic the beach-inspired texture will be.
18. Artfully Disheveled
This is for the guy who wants to look like he just walked off a high-fashion photoshoot. The artfully disheveled look is slightly more deliberate than some of the other styles on this list - it's messy, but with purpose.
This style typically features medium-length hair with lots of layers and texture cut into it. The key is creating a shape that looks intentional while still maintaining that coveted "I woke up like this" vibe.
Fashion-forward: This style often works best with a combination of products - perhaps a mousse for volume at the roots, followed by a texturizing spray and finished with a light-hold wax for definition. It might take a bit more effort, but the results are worth it.
19. Messy Slick Back
The traditional slick back is all about smooth, uniform direction. The messy version keeps the general backward movement but adds volume and texture for a more modern, wearable finish.
You'll need medium-length hair on top - at least 3-4 inches - with shorter sides. Unlike a traditional slick back, you want some volume at the roots rather than hair that sits flat against the scalp.
Updated classic: Apply a medium-hold product to damp hair, then blow dry backward using your fingers or a brush to create direction without flattening the hair completely. Once dry, use your fingers to create some separation and texture.
20. The "I Don't Care" (But Actually Do)
Last but definitely not least is the style that looks like you made zero effort but somehow still looks amazing. This is perhaps the hardest to define because it varies based on your hair type and length, but the common denominator is that it embraces your hair's natural tendencies while adding just enough product to enhance rather than fight them.
This style works with almost any length or texture and is more about the approach than a specific cut. The key is finding a cut that works with your natural hair pattern and requires minimal styling to look good.
The secret: A great haircut is essential here - you need something that works with your hair type and face shape even when you do nothing to it. Product-wise, less is more - maybe just a small amount of lightweight cream or texture spray scrunched into dry hair.</p