Top Messy Hairstyles for Guys

The disheveled and disconnected effect is one of the “trendiest” trends nowadays, that’s why it has penetrated into every hairstyle both for men and for women. Long and short, straight and curly – each type of hair is being messed up and styled naturally. Modern guys absolutely love adding some carelessness to their images as it allows to look fashionable, cool, and sexy, of course!

Diversity of Fashionable Messy Male Hairstyles

Every modern guy, who follows the trends, knows that the messy effect is one of those easy and quick ways to make a modern hipster look. Keep creative and get some unusual and stylish ideas for your next image from this list.

Long Asymmetric Disconnected Hair

1 Classic Undercut

This hairstyle is all about rebellion and freedom. The hair is cut shorter on the sides and longer at the top, disconnected with hands adding some hair product, and swept to one side.

Clean Back Messy Front Style

2 Traditional Side Part

Viewed from the back, this hairstyle looks like a typical tapered cut, clean and slick. But the front part of it is messy, with single strands falling on the face and sharp hairline, which gradually comes into the natural beard. This haircut is perfect for men with an oval face, who like classic styles with a modern twist.

Upswept Disconnected Undercut

3 Pompadour with Figured Hairline

The undercut is a very popular basis of all up-to-date hairstyles, as you can style it so different: buns, ponytails, side parts, slicked back styles, and, of course, messy hair-dos. This one has such fabulous texture of free light upswept strands.

Long and Crazy Flattop

4 Textured Swept Back Cut

Everyone is used to imagine the flat top hairstyle as some short, neat and traditional style, but it has been updated so much these days that it can totally rock! Messy structured flattop is a fresh idea for modern hipsters and fashion-mongers to stand out of the crowd for sure.

Fresh Natural Movement

5 Undercut with Massive Beard

This upswept hairstyle with curly natural texture looks pretty cool as a part of the smart everyday image. It’s very easy in styling, so it takes just a couple of minutes in the morning to get ready and look irresistible.

Curly Disorder with Sharp Hairline

6 Smooth And Flawless Hairstyle

This curly messiness is fulfilled with sharp and edgy lines on the forehead and at the beard zone, while the sides and back part of the head are blending softly. The framed beard complete the look, making it more expressive and manly.

Taper Fade Side Part

7 Slick Style for Long Top Hair

Tapered high skin fade comes into a volume blonde side part hairstyle with sharp shaved parting. The longer hair on the crown is up-styled in a bit careless way, so that the hairstyle looks messy enough, though it’s longeval at the same time.

Crazy White Caesar Style

8 Freestyle Upswept Mix

Very sloppy and disheveled, this hair seems to be unwashed for some weeks. This freaky effect does its best on medium-length dyed hair, especially white. All you need is to style your hair forward (like in classic Caesar cut), spread some hair product all over your head and disconnect it with hands.

Layered Undercut with Light Beard

9 Short Receding Hairline Cut

It’s a very interesting and unusual hairstyle that is able to express all your creativity and originality. Light, almost invisible beard flows into a great high fade, which blends into a double crown. The bottom part of it is cut straight and clean, while the messy dyed top locks stratify on it.

Blonde Hair Don’t Care

10 Rockabilly Pompadour Hair-Do

And double texture again! Like in the previous hairstyle, the bottom layer is styled into classic Caesar, while the top hair is done into a soft wavy texture.

Long Careless Style with Natural Beard

11 Simple And Sexy Thin Hair

The absolute mess in the hair is combined with a total disorder on the face. Meet a classic example of how hair can be worn longer yet still masculine without weighing a man down.

Geometry in Your Messy Undercut

12 Spiky Quiff for Fine Hair

Some angle and weight line flex, adding some sharp geometry to your haircut. Complete the crown style with structure and finesse and play a fade game for the absolutely stunning image.

Messy Curly Undercut

13 Rain Or Shine Classic’s Fine

Curly hair is perfect for various messy hairstyles. It’s disconnected by its nature, so we can style it into such fresh composition even without any extra hair products and devices. Low descending graduated skin fade and square masculine shape of the hair-do can become your perfect twists for the ideal look.

Effortlessly Cool Lion’s Mane

14 Option for Salt And Pepper Hair

This hairstyle is dangerously extreme and playfully soft at the same time. It’s a good idea for men with naturally wavy hair of medium length. Hair roots are styled back, while the hair tips are curled up – cool solution for stylish guy.

Fluffy Afro Hairstyle with Natural Beard

15 Mid-Length Hair Scissor Taper

This look is full of bold combinations and unpredictable resolutions that work wonderfully together. Let’s go top-down: first, we can see absolutely messy, the fluffy crown of African locks, disheveled with a special curl sponge for more amazing texture. Next, there are very sharp hairlines in the front and in the back and a super clean blend coming into the undone natural beard.

Nice Short Taper with a Classic Graduation

16 Free Long Hawk

Fantastic scissor game was played in order to get this soft and clean taper with a flow full square layer (which makes it kind of “flattoppy”, by the way). The texture is multidirectional and so crispy, with some single careless strands falling down the face. Bonus detail is that this hairstyle is also good for men with a receding hairline, that makes it universal for all ages.

High Curly Undercut with Freestyle Design

17 Side Part with Beard Fade

The crown of this hairstyle has a rather unusual texture as the hair is fluffy with single sloppy curls, separated with hair gel. But the salt of the image is a nice shaved pattern on the faded side that definitely makes the whole image unique.

Contrast Messy Top with Sharp Design

18 Diffused And Faded Curls

Here we go with undercut again, but much more extreme and stunning than the previous one. The first thing that makes it incredibly bright is the contrast color at the top, of course, but that’s not all. Besides it has a very sharp hard part that goes through the side to back, and a very soft blend, which emphasizes that crazy design.

Volume, Disorder, and Control for Long Hair

19 Blunt And Bold Fringe

This aggressive and defiant hairstyle will turn a lot of heads, no matter if you’re on a party or official meeting. The front part of hair should be up-styled with a blow-dryer and disheveled with fingers adding some hair product. It’s OK to look a bit crazy and bold on any occasion when you’re young and hot.

Curly Texture Flowing Forwards up Top

20 Layered Hairstyle for Mid Length

As curly hair is disheveled by its nature, it’s very convenient to create various messy hair-dos for it. If you’re bored with popular up-styles and volume bouffants, maybe it’s time to come back to something old and eternal? The well-known Caesar will come in handy in this case. Look, how fabulous it looks in combination with careless soft curls and faded beard.

“Add Some Color to Your Mess” Hairstyle

21 Modern Classics with Slick Pomp

Switch to the bright side of lifestyle with extreme colors and catchy combinations – rock a crazy dyed mess atop, add some sharp and straight hairlines in front, and a clean skin fade on the sides. Don’t forget about the beard design! For example, a long goatee with a narrow mustache will be a good idea for this style.

Textured Natural Movement

22 Slick Textured Tunnel

To achieve a square, masculine shape doesn’t mean you need to skin the sides or even trim them at all. Try this cut a little longer on the sides, especially for winter, and you’re gonna love it. Don’t forget about the texture!

Long Top Skin Fade with Design

23 Creative Curly Cut And Style

And curls again. If it’s your natural hair texture, you can hardly make it sleek, or style it in some other way, so satisfy with your perfect curly disorder and switch your creativity to the sides design. Here’s one more idea how to style them like a real piece of art. Get inspired and act.

Hard Part Messy Undercut

24 Bright Bleached Caesar Undercut

High clean fade is partially separated from the crown with a sharp shaved line, which is a hard part. The top is disconnected and a bit spiky, like the sea waves. This universal hairstyle is appropriate for any occasion and place.

Dandelion Hairstyle for Curly Men

25 Skin Fade Pomp with Razor Side Part

This round positive and messy cut is for men with naturally curly and thin hair. It’s easy to cut and extremely easy to style so that you don’t need to spend a half an hour in front of the mirror in the morning. Be creative and add your own ideas to this style, for example, play with beard and mustache.

Hipster Disorder for True Dandy

26 Hipster Disorder for True Dandy

This messy volume hairstyle is somewhere between the pompadour and taper, which is a cool combination for trendy guys. Fulfill your hipster look with an original mustache and natural beard and get ready to attract women’s eyes by means of your irresistible careless image.

Skin Fade with Man Bun

27 Skin Fade with Man Bun

If your hair is long and wavy or curly, you can leave it free or tie it into a careless bun. Complete the cut with a fantastic clean fade and sharp hairline in order to get fresh and comfortable style for everyday wear.

Sloppy Slicked Back Bright Undercut

28 Sloppy Slicked Back Bright Undercut

Make the sides and back of your head absolutely bald and try such fiery color in order to update your pestered undercut. After that add some sloppy texture to your long crown and enjoy your fresh and fashionable hairstyle.

Hipster Messy Hair with Handlebar Mustache

29 Hipster Messy Hair with Handlebar Mustache

This tapered cut is swept to one side so that the single strands fall naturally at its ease. But if you want to get the look of true hipster, the hairstyle is not all you need. Don’t forget about massive beard and long handlebar mustache as the main details of hipster’s image.

Afro Hair Don’t Care

30 Afro Hair Don’t Care

Actually, why should you care, if you have such gift as curly African hair?! It’s so easy in styling; all you need to look impressive every day is to get a perfect cut once a month. You can also experiment playing with the shape of your crown, with its color, and with the design of your blending sides as well.

Streaked Flowing Hair for Men

31 Streaked Flowing Hair for Men

This careless loose hairstyle requires naturally wavy texture of your hair for longer effect. It’s so simple and easy, but very attractive and masculine at the same time.

Messy Male Bun Option for Wavy Hair

32 Messy Male Bun Option for Wavy Hair

Long and even medium hair length has a great advantage: there are so many variants how to style it without changing the cut. Man-bun is one of them, here we have a very careless and messy top bun that looks stylish and is very comfortable to wear at the same time.

Side-Swept Long Hawk

33 Side-Swept Long Hawk

Long messy Hawk, full beard with a mustache and the undercut look delicious. All you have to do in order to achieve it is just to allow your top hair grow long and keep an eye on your fade (you can make taper like on this photo if you want to). The concept is simple.

Curly Undercut with Prolonged Hard Part

34 Curly Undercut with Prolonged Hard Part

The salt of this ordinary messy hair-do is a sharp hard line, which is shaved on the side of the head and continues on the eyebrow. Catchy idea! The best thing about it is that you can add this smart detail to any hairstyle, so keep it in mind for your next visit to your barber.

Careless Top Knot Undercut

35 Careless Top Knot Undercut

Low drop skin fade with double tap looks careful and neat, while the top is absolutely disconnected and done into a careless stop knot, which is still very popular among men.

Messy 60’s Pompadour Hairstyle

36 Messy 60’s Pompadour Hairstyle

Don’t write off the good old pompadour when it comes to messy styles. Despite the hair should be swept back for this hair-do, it’s easy to add some modern twist and make it textured and disheveled a bit.

Messy Idea for Thick Hair

37 Messy Idea for Thick Hair

The more hair you have the better style you get, so this textured oversized hairstyle is definitely an option for thick full hair. It’s a perfect option for a job interview, business lunch or another routine. So ideal, disconnected and volume at the same time cut can’t fail to play into your hands under any circumstances.

Silver Fox in Natural Disorder

38 Silver Fox in Natural Disorder

When you feel bored of changing your cuts, it’s time to change the color! Seriously, it works even more! This messy tapered undercut definitely looks much brighter in this stunning color, than if it was naturally dark, right?

“Ready to Play” Messy Top Knot

39 Ready to Play” Messy Top Knot

This top knot mess is forgivable, as the “Pokemon GO” logo design on the nape tells that you’re a rapid fan of this game and have no time for doing your hair neatly. Besides, it can inspire you to create some other “picture” on your bald sides or back part of the head, depending on your interests.

Breezy & Light Streaked Hair

40 Breezy & Light Streaked Hair

If you feel extremely comfortable, when there are no any hair products or bulky constructions on your head, this weightless natural hairstyle for medium length is for you. The breezy effect is increased by means of streaked strands all over this side part free hair-do.

Mr. Irresistibility Hairstyle with Stubble

41 Mr. Irresistibility Hairstyle with Stubble

Long top hair is styled here in a rather unusual manner. One part of it is swept back like a pomp while the rest of it is falling naturally to the sides with single strands on the face. It’s obvious that manly stubble and ‘stache perfectly suit this hot and sexy look.

“Just from Bed” Style

42 Just from Bed” Style

Why not? It’s your life and you can create everything you want. When you stop worrying about what others say, they’ll stop talking. Let this messy hairstyle become your inspiration for the new crazy image of your own.

Masculine Bun with Full Beard

43 Masculine Bun with Full Beard

In spite of the bun initially was a women’s hairstyle, nowadays it can be very manly as well. Especially, if your careless bun with loose strands near the face is combined with a full brutal beard and mustache…wow, it’s a perfect style, for sure!

Handsome Spiky Hairstyle for Guys

44 Handsome Spiky Hairstyle for Guys

Meet another shaggy but handsome image for fashion-hunters. This rather simple spiky cut for mid-length dyed hair is very smart and sweet. Besides, it’s very easy in maintenance: you should only take care of fixing your crown up. The tapered sides are your barber’s responsibility and the beard…just let it grow, dude.

Magnificent Dyed Pomp

45 Magnificent Dyed Pomp

This fantastic volume is definitely not for everyday wear, but it should be definitely born in mind for some special occasions and events. Tapered sides and long dyed crown can be easily turned into a top knot, ponytail or side part for casual lifestyle and become such magnificent pomp for the important day of your life.

Hair-Do of Freedom for Mid-Length Hair

46 Hair-Do of Freedom for Mid-Length Hair

This hairstyle is one of the best options for men with naturally wavy hair, who don’t like spending too much time styling their manes. Undone beard and streaked locks will add even more lightness and carelessness to this image.

A Vintage Style Is a Gentleman Style

47 A Vintage Style Is a Gentleman Style

Yes! It’s unbelievable, but messy hairstyle can be classic and elegant as well! Just look at this photo and verify this. Side-swept “arranged disorder” is an ideal variant for business lunch, important event, promising date, and informal party as well.

Brunette Spikes in Disorder

48 Brunette Spikes in Disorder

This completely disheveled upstyle is something between the 220 volts impact and effect of upside down photo, but anyway, it’s something fresh and catchy for your hair. Break the rules and rock this fantastic spiky hairstyle.

Full Bun for Long Unruly Hair

49 Full Bun for Long Unruly Hair

The man bun is alive; it’s extremely popular among men of all ages. Besides its fashionable look, it’s incredibly comfortable for guys with long hair. Full beard? – Nice choice! Rock it and enjoy hipster casual style.

Careless Perfection Is Not a Crime

50 Careless Perfection Is Not a Crime

This sloppy hairstyle looks like it has not been cleaned for ages, but still, it has lots of ardent fans and admirers throughout the world. If you’re ready to keep dirty for months – this baby is for you! Huh, just kidding. All you need to reach this messy effect is to spread some styling product over your washed head with fingers, without combing it.

Bunch of Blonde Curls Taper

51 Bunch of Blonde Curls Taper

Spirit of rebellion and freedom permeates through this disheveled curly crown, which is swept forward and softly dyed. Such brutal style will become the icing on the cake of your bold and confident image.

“Rules are Made to be Broken” Hairstyle

52 Rules are Made to be Broken” Hairstyle

This look definitely proves the saying above – creativity has nothing to do with rules. Don’t worry about experimenting with the shape of your crown, grow a full beard or long mustache, create fantastic texture, whatever. When it comes to your individuality, nothing is banned.

Eternal Leo’s Style

53 Eternal Leo’s Style

Remember the Titanic movie, huh? Don’t you want to try that legendary Jack’s hairstyle that swept women off their feet? The secret is in naturalness: make sure your hair is messy, but not too much, clean, but still a bit sloppy, and falls naturally and free.

Long Curly Hair with Fantastic Texture

54 Long Curly Hair with Fantastic Texture

As is known, lucky guys with curly hair texture have much more chances to get the ideal careless look without extra efforts, but for some reasons, the majority of them prefer hiding their fabulous hair behind various shortcuts. And in vain! Such gorgeous hair is an envy both for men and for women, take advantage of your gift and shine with your magnificent locks.

Keep Calm and Have Fun Hair-Do

55 Keep Calm and Have Fun Hair-Do

Paint your black-and-white weekdays with bright and rich colors by means of new stunning haircut with dyed freestyle design. Such hairstyle is very convenient, as you can dissolve the bun anytime and none’s gonna see that crazy piece of art on your nape.

Merman Texture for Fashion-Hunters

56 Merman Texture for Fashion-Hunters

The wet effect is another way to make your hairstyle messy and sloppy. The hair gel is usually used for this purpose. You need to wash your head, dry it with a towel and spread some gel all over your hair, disconnecting it with hands at the same time.

Dyed Messy Style for Straight Hair

57 Dyed Messy Style for Straight Hair

This hairstyle is an absolute champion among lazy guys with straight long hair who like stylish images. Nobody  will distinguish whether it has been styled with special hair products or you’ve just overslept and run out without looking in the mirror – that’s how perfect you’re gonna look!

Dreaded Afro Mess with Full Beard

58 Dreaded Afro Mess with Full Beard

If you have already seen dreaded mullets or hawks, this dreaded undercut won’t surprise you. Let your dreadlocks live their own life, falling messy to all directions, and rock such hairstyle just to change something in your life.

Shabby Tapered Undercut
59 Shabby Tapered Undercut

Do you want some crazy messiness on your head? Don’t go to your barber in time. Seriously, just let your taper grow longer than it should be and voila – effortlessly disheveled hairstyle is done.

Male Half-Bun Undercut

60 Male Half-Bun Undercut

This hairstyle is something between an undercut with a top knot and a male half-bun. This confusion arises because the sides and nape are not trimmed, but also not long enough for half-bun. But, anyway, this baby is very catchy, appropriate both for a smart and casual look.

Fluffy Beard and Full Bun

61 Fluffy Beard and Full Bun

Here’s one more idea to inspire you for fashionable manly beard style. Messy full bun and shaggy beard – what can be more brutal, than this?

Clean and Messy – All in One

62 Clean and Messy – All in One

Modern tendencies claim absurd mixes of absolutely different styles, shapes, colors in order to get something new and unique. Here we have a blend of clean beard and ‘stache, fantastic skin fade and absolutely undone disconnected crown, which surprisingly works perfectly for this contemporary image.

Organized Chaos Hairstyle

63 Organized Chaos Hairstyle

Crazy, but sexy, this hairstyle will become a wonderful modern twist for your classic look. With such up-style, your business is gonna take off with lightning speed.

Braided Pompadour with Absolute Mess

64 Braided Pompadour with Absolute Mess

It’s not a secret that braided hairstyle has become incredibly popular among men, so here’s an idea how to perform some mess with volume in front and well-known French braids.

Rad Pink Mohawk Style

65 Rad Pink Mohawk Style

Wow! That’s definitely not your average bear! If you’re one of those lunatics who are able to play so large, don’t lose time – go and rock such striking messy Mohawk with wavy texture and add your favorite color.

Long & Wavy Streaked Hawk

66 Long & Wavy Streaked Hawk

Messy long Hawk, swept to one side, full beard and fancy glasses are super cool. All you need to get this hairstyle is to grow your wavy crown long enough, streak it and then add an undercut.

Half-Bun for Brutal Men

67 Half-Bun for Brutal Men

Half-bun, like a traditional full man bun, comes from women’s hairstyles but has been adjusted for manly images nowadays. Such hairdo means that the top part of the hair is done into a loose bun, while the rest of it is flowing down the shoulders naturally.

Smart Messy Style on Straight Hair

68 Smart Messy Style on Straight Hair

How about straight blonde carelessness for today? All you need is to dishevel your hair with hair pomade with fingers, without combing it and let it fall naturally.

Nape Knot with Cute Curls

69 Nape Knot with Cute Curls

Nothing special – it’s just an ordinary careless knot on the nape with some free strands near the face. But how comfortable this hairstyle is for any activity you do and appropriate for any circumstances you appear in.

Flawless Swept-Forward Mess

70 Flawless Swept-Forward Mess

To get this hairstyle, you should grow your top hair so that the front part is longer than the back part. In order to achieve such messy texture put some pomade on your fingers and chaotically spread it over the crown. But if you want something more than a textured wavy hairstyle, play with fade or complete it with beard design.

Undercut Ponytail with Long Beard

71 Undercut Ponytail with Long Beard

They say that the opposites attract, and this look is a perfect proof. At first sight, a messy disheveled natural beard and no less disheveled pony are absolutely incompatible with clean faded sides and sleek top, but they work incredibly together.

Stunning Braided Blonde Mohawk

72 Stunning Braided Blonde Mohawk

72 Stunning Braided Blonde Mohawk 1

As you can see, this braided Mohawk with an organized mess is very flexible. With this haircut, you’ll have millions of options how to style it according to your mood and each of them is gonna be super catchy, unique and crazy. Don’t afraid of experimenting with your hair – it’s fun!

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