Messy Haircuts for Men

Messy Haircuts for Men

There are few things sexier than the effortless, tousled look. Delightfully unkempt yet controlled, messy hair has made a huge comeback in the last few years. Some men have rocked the “I just rolled out of bed” look for years; the key is maintaining control of the mussed locks and keeping things devilishly wild without going full “I have not brushed my hair in three days and there may be a small bird’s nest hiding somewhere near my scalp”. Here are some of the best cuts, colors, and styles for achieving the effortless yet clean messy look at home. 

1The Hipster

The natural looking locs of this look is controlled with a pomade or wax to give them texture and shape. The wild loose hair on top is somewhat tamed by the neatly trimmed, slightly shorter sides and sides and back of this cut, creating a perfectly harmonious relationship between “clean-cut” and “bedhead”.

2The Rockstar

Something a little more bold, this cut features an undercut side and back with a grown out top that is slightly backcombed. Perfect for someone looking for a low effort look, this cut is easy to maintain and gives the option for a man bun or a daring side shaved, modern twist on the classic pompadour.

3Romantic Layers

This swoon worthy look is giving us romance novella love interest vibes. The long locks are layered to give texture and shape to the hair and held in place with a wax or pomade. Another easy to maintain cut, this option is perfect for the guy on the go. You can literally just run a bit of pomade through it, tousle with your fingers, and be out the door!

4Natural Curls

Perfect for those with naturally curly hair who want to control their rings without chopping them off, this look pairs a shortened side with tons of volume and layering towards the top of the head. This gives a bouncy look that is totally drool worthy and practically begs to be played with. 

5The Weekender

With a gentle fade that meets a harsh, short layer before gradienting into a voluminous, choppy cut top, this cut is a fun, slightly grown up play on a classic mohawk look. You get all of the punky, confidence exuding spark of a mohawk while maintaining the ability to pull everything together for a meeting friendly style. 

6The Long Caesar

A lengthened twist on the oh so 90s caesar hairstyle, this look makes quite the bold statement. Typically, a caesar cut, named after the great ruler Julius Caesar, showcases blunt, horizontal bangs cut directly across the forehead in a stark contrast to the rest of the controlled fade used on the rest of the head. Instead, this variation leaves the hair long and messy, creating a sort of “relaxed emperor” look. 

7Two in One

The simple yet drastic fade and long top of this cut creates the perfect canvas for a bit of experimentation. You can go from straight and slicked back to curly and wild with minimal effort, making it perfect for those who work in a formal setting but still like to be able to control their look outside of the office. 

8On the Go

Quite possibly the easiest messy look to maintain, this short cropped, layered look is perfect if you want something low maintenance but still shaped. The choppy layering gives texture and interest to the hair, avoiding the flat look that can often come with buzzed down locks. Amplify these layers with a bit of pomade to give a little hold to the chopped bits.

9The Viking

Want to look like a warrior? Look no further than this viking-esque, super messy look. The grown out, shaggy, and lightly layered cut is complimented by a single, thick braid to add a bit of interest to the front of the cut. Pair this look with a beard and you have a truly sexy, daring look that can go from messy to man bun in thirty seconds flat. 

10Go For Height

If you have a lot of curls, rock a voluminous look by asking for a cropped side and layered top like Andrew Garfield’s in the photo above. The look is eye catching yet wearable and slightly understated, matching well with current trends and giving wiggle room for experimentation. 

11Lots of Layers

There is a sort of trend with a lot of messy hair styles: layers. If you want to achieve the volume and bounce of the picture above, ask for lots of long layers with most of the volume focused towards the longer half of your part. Simply style with pomade for a little grip and you are all set. 

12Color Contrast

To give your messy locks an otherworldly appeal, try playing with bold colors. White strands are super trendy right now, especially with choppy layers and a long fade like pictured above. 

13A Feminine Twist

A classic look for women is making its way into the realm of men’s hair as of late. Featuring long, face framing layers and sideswept, grown out bangs, this look is dreamy yet still distressed enough to maintain a sort of soft masculinity. 

14A Stark Contrast

If you want something a little younger, stark shaves are really in right now. Try something like the photo above if you are hoping for a dramatic, eye catching look that is still relatively easy to maintain. 

15The Side Caesar

No, we do not mean the salad. This take on the Caesar hairstyle is a bit longer and is also softened a bit by the bangs being swept to one side. Great for those with face shapes that do not suit angular cuts, this is an easy cut that is simple to style and great for office settings!

16Pushed Back

If you want a sort of effortless look like Bradley Cooper’s in the photo above, ask for lots of soft layers. Simply brush the hair back and hold it in place with some pomade for a bit of grip and texture. The controlled chaos of Bradley’s hair makes this look suitable for office or high end settings without sacrificing length. 

17Side Swept

Another professional yet messy look, this one opts for a more side swept styling. Ask for layering and lots of volume on top to help achieve this look! 

18Swept Back Waves

Nothing says “I do not care” quite like having your hair haphazardly pushed back from your forehead. The messy waves and singular length used in this cut compliment the look well and gave a sort of low effort bad boy vibe that is super in right now.

19The Boy Band

A complete 180 from the swept back, carefree look, this cut carries quite a bit of boyish charm and is ideal for those with curly hair types. Ask for long layers to help create volume to get the full effect of this fun, youthful look.

20The Graphic Side Shave

A sort of “bad boy” look, this is a classic side shave with a long top plus an added twist. Pictured above is a simplistic, stark line shaved into the cut but you could also opt for designs or even colors to create your perfect, super bold look. Keep the top messy for a sort of punk rock vibe. 

21The “Samurai Bun” 

A variation on the ever trendy man bun, this half up, half down hairdo works best with a sort of one length or perhaps very lightly layered cut. Pull half of your hair up around the crown of your head and pin or tie it with a hairband to create a timeless, heroic sort of look.

22Viking Volume 2

Go long and natural this year and opt for a viking cut that is as easy as it comes. Long layers or a one length cut that comes down to the mid-chest area and can easily be swept into a bun, braid, or ponytail as needed through the day. This one is especially great for those who want the stunning, novel worth length without sacrificing their ability to go about their day as usual.

23Controlled Side Sweep

A choppy version of the classic side swept bangs has been making a shocking reappearance on social media as of late. Parted to the side, this cut can be worn long or cropped to fit any work environment without sacrificing ts boyish charm.  

24The Swoop

With heavy layering up top and a semi-cropped cut on the sides, this cut offers a lot of variety in terms of styling. For a messy yet controlled look, use a texturizer to help swoop the long bangs to one side, creating an arc over your eye by combing the hair up and slightly back. 


If you are hoping for that windswept, “I have been skating and surfing all day and could not be bothered to comb my hair” look, try showing your stylist something like the photo above. Long layers and curls give texture and interest while pomade is used to sweep the hair slightly forward to give it a wind blown appearance.

26Something Edgy

This look is not for everyone but certainly makes a statement. The mash up of styles draws from fauxhawks, fade cuts, and side shaves for a truly modern and interesting look.

27The Modern Bowl Cut

This one is a bit of a simple cut that looks great on those with naturally curly hair. Just ask for the hair to be thinned a bit (or undercut) and trimmed to roughly all one length. Part to one side and style with texturizer for a voluminous, fun take on a classic hairdo. 

28Blunt Bangs

If you are hoping for something intense and creative, give blunt bangs a try. A fan favorite among hipster girls and effortless chic women alike, these statement bangs look great when paired with a short mop of controlled waves.

29The Low Man Bun

While many men go for man buns on the top of their heads, this look is a bit more low maintenance. Just tie up the hair at the nape of your neck, leaving some strands hanging for a sort of careless, “I did not have time but somehow still look amazing” look. 

30The Widow’s Peak 

This angular look is great for those with a naturally forward hairline or those looking to mimic the dynamic, daring look. Similar to side swept bangs, ask for the hair at the front of your head to be left longer and the sides cut shorter to give an intensely voluminous look that is easy to style on the go.