41 Messy Medium-Length Hairstyles for Men

Just a few minutes will earn you major style street cred.

Medium messy hairstyles are a go-to for guys for a reason: They’re easy to create and have that effortless ‘I woke up like this’ vibe that’s so sought after. That said, we’ve created a collection of messy hairstyles men can create in five minutes or less.

We’ve included many different variations of messy hairstyles men can quickly and easily make their own, so there’s no question about whether or not you’ll find something that suits you. Read on:

41 Messy Hairstyles for Men Trending in 2023

When picking out messy hairstyles, it can be a challenge to know where to start, so we’re here to help. Check out 41 looks that are perfect when achieving messy medium-length hairstyles for men.

1. The Thick Hair Solution

Short Curly thick hair
Learn how to make this look work for thick hair

The only thing better than a classic messy style is the same look created on thicker hair. The more messy hair you have, the better, right?

2. Messy White Hair

messy hairstyles for men white hair
How to make this look work for white hair.

There’s no age limit when it comes to this style. Pair your messy white strands with a trimmed beard to give the look a more youthful spin.

3. Windblown Messy Hair for Men

messy hairstyles men windblown
How to nail an effortless windblown style.

This messy style gives the impression that you just climbed off your motorcycle and ran your fingers through your hair. Irresistible, right?

4. Spiky Messy Hair

messy hairstyles for men styled blonde
Make it a styled mess.

Rocking a messy look doesn’t mean you can’t style your strands. Run AXE Clean Cut Look: Classic Pomade through your hair to give it a little shape. Using a pomade is a great way to achieve the messy hair look while still having control and shape to the style.

5. Spiked Up Front

messy hairstyles for men spiked front
Keep the mess to a minimum.

Use a little bit of hair gel to spike up the front of your hair and keep the messy look to a minimum. This adds some texture to your strands, making it the perfect mix of not too messy, but not too perfect.

6. Messy Fade

messy hairstyles for men messy fade
Pair it with a trendy fade.

Pair a messy style with a fade haircut to nail two trends at once. This look is sure to be a go-to for a long time.

7. Woke Up Like This Messy Hair for Men

messy hairstyles for men medium brown
This is by far the easiest variation of this style.

In the ultimate ‘I woke up like this’ style, all you have to do is sleep on damp hair and run your fingers through your strands when you wake up. Easy enough, right?

8. The Messy Man Bun

guy with effortless long messy bun
You don’t need a pristine look each time.

The women in your life are no doubt big fans of the messy bun. Get in on the love and create one of your own. This trend is great because it’s also practical for guys with longer strands. Need to keep your hair out of your face? Try a man bun!

9. Loose Curls

messy hairstyles for men long curls
Brush your curls out.

Looking for messy hairstyles men can wear without too much effort? Simply grow out your hair. The longer length will create the perfect messy style.

10. Messy Hair Boy Looks: Wet Hair

messy hairstyles for men gelled wet hair look
Load up on the hair gel.

Hopping on to the messy hair boy trend is so easy to do! To achieve a wet hairstyle like this, brush your hair forward and spritz it with a flexible hold hairspray like Dove Style+Care Flexible Hold Hairspray to keep it in place without making your hair hard and crunchy.

11. Sweep it to the Side

messy hairstyles for men fade messy top
Streamline your messy look by sweeping it to the side.

Streamline your messy look just a bit by sweeping it over to the side. This is a great way to still achieve the messy hair for men look, without having to deal with your hair in your face all day.

12. Effortless Short Messy Hair for Men

messy hairstyles for men effortlessly styled
Learn how to effortlessly style your strands.

This style allows you to work with your natural texture rather than against it. Skip the hair products and let your hair do its thing.

13. Messy Style for Thinning Hair

messy hairstyles for men curly dark brown
A messy style can help conceal thinning hair.

Consider this style if you’re dealing with hair loss or thinning hair. A messy style can give the illusion of thicker strands.

14. Embrace Your Cowlick

messy hairstyles for men cowlick brunette
Work with your cowlick rather than against it.

Use your cowlick to add a touch of easy volume to the front of your messy style. This can help create a natural swooping effect, adding to the overall messy texture of the look.

15. Combed Over (In a Good Way)

messy hairstyles for men combed over
A new definition for the combover.

Want to achieve that teen heartthrob messy hair boy look? Comb all your strands over into one direction for the ultimate messy style. Bonus points if your hair is long enough to flip out at the ends! If you need extra styling help, a dollop of AXE Messy Look: Matte Gel will do the trick.

16. All Combed Back Medium-Length Hair for Men

messy hairstyles for men combed back volume
Pair volume with a combed-back style.

Amp up the volume by teasing your hair at the roots and combing it back. This adds messiness to the style while still being controlled.

17. A Grungy Messy Style

messy hairstyles for men combed back
Incorporate the grunge factor.

Messy meets grunge in this trendy and edgy style. We love this look because it’s appropriate for such a wide variety of occasions.

18. Classic Bowl Cut

messy hairstyles for men classic bowl cut
Give a classic bowl cut a new spin.

Revive a classic bowl cut by embracing a messy texture and make the look more current by incorporating this messy trend.

19. Business Casual

messy hairstyles for men businessman brunette
A business-appropriate take on a casual style.

Concerned that you won’t be able to find a messy style that’s appropriate for work? Use this clean-cut look for inspiration.

20. Modern Messy Hairstyles for Men with Bangs

messy hairstyles men bangs
You can make bangs work – here’s how.

Opt for a messier style and let your bangs air dry for a super laidback look. This shows off the natural texture of your strands, which can lead to a messier style.

21. Centered Afro

messy hairstyles for men natural hair
Let your afro free with this style!

Keep the sides of your hair short, and let your afro go all natural in the center. This will create a truly effortless look.

22. Pushed Back Front Medium-Length Hair for Men

messy hairstyles for men pushed back style
Who said styled hair can’t still be messy?

Use wax or lightweight gel to push up the front section of your hair. This will give you a messy but still styled look.

23. Swept to the Side

messy hairstyles for men swoop to the side
Push hair to the side for a messy style that’s out of your face.

No messy short hair for men’s list could be complete without a stylish side-swept look. Not only will this give you a messier style, but it will also keep your hair out of your face.

24. Tousled Front

messy hairstyles for men Tousled Front
Mess up the front of your hair for a stylish, yet tousled look.

If your hair is slightly shorter on the sides, mess up the front section of your hair for a stylish yet tousled style.

25. Front Standing Up

messy hairstyles for men Pushed Back Front
Push back the front of your hair for a messy style that stays out of your face.

Style the front section of your hair so it stands up in various directions. This will give you the ultimate messy hair for men look.

26. Free-Flowing Curls

messy hairstyles for men Free Your Curls
Nothing says messy like free-flowing curls!

Let your natural curly hair shine. To achieve this messy look, all you have to do is air dry your curls and you’re all set! We love Suave Men 2-in-1 Shampoo + Conditioner with Shea Butter & Coconut Oil, with coconut oil, shea butter, and hemp seed oil to keep your locks soft and moisturized.

27. Lived-In Messy Style

Messy Hairstyles for Men Center Style
Mess up the center section of hair for a lived-in look.

Create that lived-in messy medium-length hair for men by pushing the center section of your hair to one side.

28. Stick Straight

Messy Hairstyles for Men Stick Straight
For a messy, yet styled look, stick the front section of hair up!

Use a gel to stick the front center section of your hair straight up. This adds texture and volume to your style while still having control and light hold.

29. One-Sided Messy Style

messy hairstyles for men one side
Add a little finesse to your messy style.

Use a gel to create a voluminous one-sided messy style. Whether you’re going out or going to a fancier event, this style works for both!

30. Messy Hair Men Woke Up Like This Style

Messy Hairstyles for MenJust Woke Up Look
Hey, maybe you did wake up like this? If so, leave it for a messy style!

So, you woke up and your hair is sticking out in practically every direction? That’s perfect for this style! If you want to neaten up any pieces, use wax to help hold the hair in place.

31. Short and Sweet Messy Hairstyles for Men

Short messy look
A short and sweet style can do the trick!

Who says short hair can’t participate in the messy styles too? Use a lightweight gel to help hair stick out in different directions.

32. Messy Hairstyles for Men: Stylish Waves

Messy Hairstyles for Men Stylish Waves
No need to have picture-perfect styled waves.

No messy look list would be complete without some wavy medium-length hairstyles for men inspo. If you’re blessed with wavy hair, let them air dry and then this style is all set! There’s no need for picture-perfect waves for this messy look.

33. Messy Hair Boy Parted Curls

Messy Hairstyles for Men Parted Curls
Add a side part to your curls and you’re good to go!

Change up your typical style by adding a side part. Switching up your part can make a huge difference even if it is a messy look!

34. Messy Hairstyles for Men Man Bun Style

messy hairstyles for men messy man bun
If your hair is long enough, you can never go wrong with a man bun.

Don’t want to deal with messy hair at all? If you’re stuck in a rut, go for that laid-back look and create a messy man bun – you can’t go wrong here!

35. Dreadlocks Style

messy hairstyles for men dreadlock hairstyle
If you’ve ever wanted to try dreadlocks now is the time to!

Ever wanted to try dreadlocks? Now it’s your chance to try this ‘do out! If you already have dreadlocks, try wearing them in a ponytail or bun.

36. Voluminous Quiff

Messy Hairstyles for Men Voluminous Quiff
You can never have too much volume!

When your hair is still wet, use a hairdryer to brush the center section in an upward motion to create a voluminous quiff style.

37. Messy Volume

Messy Hairstyles for Men Messy Volume
Still want more volume? Opt for this look!

So, maybe you want all-over volume? Dry your hair in the same upward motion as mentioned above, and you’ll be on your way to sky-high hair!

38. All-over Messy Hairstyles for Men

Messy Hairstyles for Men Mess and Go
This look will have you out the door in no time!

All you have to do is warm up a dime-sized amount of hair wax in your hands, run it through your hair for a lightweight messy hold, and then you’re all set! It really is that easy!

39. Messed Up Center Style

Messy Hairstyles for Men Messed Up Center Style
Mess up the center of your hair for an effortless style.

If your hair is shorter on the sides and longer in the center, opt for a messy center style. Just use a lightweight gel to push the center section of hair back and to one side then you’re all set! Don’t worry, you don’t have to be too neat with this style.

40. Messy Hair Boy Disheveled Style

Messy Hairstyles for Men Disheveled Style
The ultimate messy, but still styled look!

This disheveled look can quickly be achieved with a small amount of gel. All you need to do is run a dime-sized amount of Dove Men + Care Well Defined Taming Gel through your hair to achieve the ultimate messy, but still styled look!

41. Medium Messy Hair

guy with messy medium length blonde
Go for a medium messy fade hairstyle.

Experimenting with a medium-length fade haircut is the perfect way to try out a messy hairstyle. The longer length at the center of your hair is perfect for creating a messy look.

How to Achieve Messy Hairstyles for Men

Achieving a messy hair look isn’t complicated at all. You can easily do this in no time with just a few products.

messy hairstyles for men messy hair brunette scruff
Pair your messy hair with a closely shaven-beard. Photo credit: Indigitalimages.com

How to Style Your Messy Look Men’s Hair

Creating messy hairstyles for men is incredibly easy. If you’re familiar with any of the aforementioned rules, you know that a great style starts in the shower. Suave Men Thick + Full 2-in-1 Shampoo + Conditioner is the efficient thickening wash and care system of your dreams. Give your hair a boost and prepare for strands that feel and look thicker after just one shower. Simply massage the product into wet hair, let it foam up into a lather, and rinse thoroughly.

After your shower, you’ll want to towel dry your strands before raking Bed Head for Men Pure Texture Molding Paste through your hair. Whether you’re working with hair that’s on the shorter side or you’ve grown your strands out into longer locks, this styling paste will add loads of texture and movement to your hair.

messy hairstyles for men messy hair blonde long skater
This style works on hair of any length. Photo credit: Indigitalimages.com

Lastly, mist your hair with Suave Extreme Hold Unscented Aerosol Hairspray. This unassuming hairspray will lock your texture in place and give your hair an intentional finish. The results? Easy, messy hair that will give you that bad boy meets fashion week vibe.

Now that you’ve gotten a true taste of messy hairstyles for men, you have plenty of inspo to choose from! Be sure to take a picture of your style and tag us @AllThingsHairUS! Happy styling!

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