Carefree Hairstyles
cookiestudio / Shutterstock.com

Running Wild: 10+ Tousled and Stylishly Disheveled Hairstyles You Should Try

After all, you’re not just all work and no play

written by The Editors

The short, clean-cut look can send the message that you are a professional person and likewise a very serious man., On the other hand, loose hair can convey that you’re more fun, but more importantly that you don’t take yourself too seriously. These next 10+ styles are great examples of how you can blend these two seemingly contradictory ideas to get the best of both worlds.

1 / 16
Disheveled Care Free Medium Hairstyle

Disheveled Care Free Medium Hairstyle

Nowadays, bedhead hairstyles require a tad bit of maintenance. Be ready to grow your hair to medium length and get it layered (and make sure to have it trimmed every two months or less if your hair grows faster). Your number one companion is a hair product that specifically states that it’s for creating the bedhead look, and all you have to do is slather this product on your hair, and voila! You have achieved a disheveled look without greasy hair. Don’t sport it with a beard to achieve a more clean look.

2 / 16
Tousled Side Part

Tousled Side Part

Half angel or part devil? This haircut creates a clear distinction between two joined hairstyles – a tousled part and a clean side part. The tousled part gets 2/3 of the hair while the other gets 1/3. Because of this fraction, make sure that you choose the side where the tousled part goes, as it can’t be interchanged. The haircut is flexible enough that if you don’t want the tousled part to be messy, you can also put it down. Best worn without a beard and minimal accessories for full effect.

3 / 16
Carefree Short Tapered Hairstyle

Carefree Short Tapered Hairstyle

This short tapered hair style is cleaned up around the sides of the hair while being textured at the top. The textured top gives it a more tousled and stylishly disheveled look, but the hairline is kept clean and sharp to add shape to the style.

4 / 16
Undercut with Layered Spikes

Undercut with Layered Spikes

An excellent, less radical alternative to a mohawk hairstyle – a short undercut with spiky hair on top. Not only does such a haircut look fabulous with darker hair colours but also with bleached highlights or a fully dyed top in neon green, purple or any other popping shade of pallet.

5 / 16
Care Free Scissor Cut with Shaved Sides

Care Free Scissor Cut with Shaved Sides

Feathered, roughly cut hair strands, freshly trimmed beard and low temple fade on the sides – that is the secret of a highly attractive-looking face! This isn’t a style that suits everyone, but if you’ve got that intricate taste in fashion you would definitely want to try out this haircut. A tiny crystal in the nose can also split the difference in your overall style.

6 / 16
Wavy Medium Length Mess
@thecommodoreatl/ Instagram

Wavy Medium Length Mess

Bless this mess, if you’ve got long to medium length hair, this modern look is a great way to show it off. Pairs well with a clean-shaven face, or a neatly trimmed mustache, it’s great for the modern artist who frequents coffee shops and skateparks. Orderly, yet chaotic and visually balanced while the length declares to world the exuberance of your youth.

7 / 16
Medium Carefree Scissor Crop
4774344sean / Shutterstock.com

Medium Carefree Scissor Crop

With cropped hairstyles being all the rage nowadays, this scissor-cut style is a great way to add flair and uniqueness to an already tried and true hairstyle. The hair on top is left intentionally longer than in your standard crop, while still being cut in the same fashion. The main deviation in this style is that clippers aren’t at all used for the sides or top.

8 / 16
Wake Up Texture
@mattjbarbers/ Instagram

Wake Up Texture

A slightly more carefree version of the popular Caesar cut. This style adds a bit of a wild side to a standard clean-cut style. Great for those who want to breathe new life into their look, while all the while not veering too far off the beaten path. Much like poetry, the sides are governed by strict form; a clean fade that gradually ascends into a plateau of hair, surging forward towards the front like the mighty Mississippi river.

9 / 16
Messy Curls Lying Around
@kevinluchmun/ Instagram

Messy Curls Lying Around

With the recent popularity of HBO’s Game of Thrones, the character John Snow has made curls this year’s hottest trend. And if you are one of the few lucky chosen ones to have been graced with naturally curly hair, this next medium-short length style is just for you. From top to bottom, this style allows your curls to freely emanate from the top; in much the same way as a Tuscan grapevine.

10 / 16
Pushed Side Strands
@jelle.vissers/ Instagram

Pushed Side Strands

If you liked Charlie Sheen’s hair in the classic teen comedy Ferris Buller’s Day Off, but are worried that it hasn’t aged well, then this next hairstyle is just for you. It’s a similar style but utilizes shorter hair on the top. The fade is tighter and gives the impression of hair fading directly into the skin while blending the tone of the skin with the hair. The hair on top hangs slightly over the sides giving a nice callback to that classic 80’s look.

11 / 16
Around The World Fringes
@joshlamonaca/ Instagram

Around The World Fringes

To really give off that messy-hair-don’t-care attitude, get a choppy layered cut and wear it in a disheveled style like this. And make sure you get deliberately lopsided and choppy bangs as well to complete the rockstar look.

12 / 16
Reflected Neckline with Casual Strands
@beholdthybarber / Instagram

Reflected Neckline with Casual Strands

Adding an extra cool element to your messy hairstyle results in an even bolder look. Here, the neckline features a line design that provides a sleek contrast to all that mess at the top.

13 / 16
Side-Swept Messy Long Waves
@nigel_vanderhorst / Instagram

Side-Swept Messy Long Waves

It’s easy to channel your inner rockstar with the right hairstyle. Just wear your hair long and wavy and give it a deliberately unkempt appearance and voila! The signature ‘do of all famous rockstars!

14 / 16
Tousled Top with Angular Fringe

Tousled Top with Angular Fringe

If your hair is at least two inches long, and you want to experiment with fringes, then this tousled top with angular fringe is for you. All you have to do is choose which side you want your fringe to come from, angle it to the side (not just comb it down) and create more texture on the top part of your hair by tousling it with products. The result is a mix of texture, depth, and just the right amount of edge. If you want to commit to the angle by which your fringe ends, draw a straight line from that to your eyebrow and create shaven lines.

15 / 16
Messy Top with Shorter Sides
@jodytaylorhair/ Instagram

Messy Top with Shorter Sides

A style closely resembling the wake-up texture, the main difference here is that this style doesn’t use a fade. The hair lightly guided forward while the sides remain short and sweet. We recommend asking your barber to use a 6 or a 7 on the sides.

16 / 16
Wavy Textured Messy Top
@joshconnollybarber/ Instagram

Wavy Textured Messy Top

Ever wanted to feel like a gladiator in Roman times? This style is short enough to get the work done while maintaining a degree of freedom that shows to the world that you’re not afraid to get your hands dirty. The sides are razor thin while the rest of the hair is completely scissor trimmed. Great for putting your hands up and asking that iconic question to your friends, “Are you not entertained?”

Related topics Medium