Messy Hair Boy’s Styles | 15 Easy & Trending Looks

Messy hairstyles for boys are always popular, but recently, the tousled, carefree styles have really stolen the stage. The key to messy hair, boys, is using a little of the right types of products and letting your hair do the rest. We’ll show you how along with photo examples in our style guide! 

Looking for Messy Hairstyles for Boys?

What is it about messy hair that we love so much? It lends a soft, kind of mischievous look to your style and adds a nice levity and carefree vibe.

Messy hair doesn’t make it look like you don’t care – unless you’re choosing the wrong style entirely. A good messy hairstyle will give you a cool and confident vibe that says “I woke up like this” in the most flattering way. 

The art of rocking a messy hairstyle is just that – an art. It’s not a science. You can’t make a messy style look good by carefully preening and combing each section perfectly.

It has to happen somewhat naturally by letting the bends, curls, cowlicks, and chaotic pieces in your mane finally have their moment.  But make no mistake – pulling off a cool and trendy messy hairstyle for boys doesn’t mean letting your hair do what it wants while you helplessly watch.

It’s forming a loose framework for your hair using the right types of hair products and letting the little quirks and characteristics that make your hair unique shine through in a flattering way. 

It’s really easy to style your hair in the trendy messy/tousled way.

And there are tons of options to choose from if you’re a fan of this look! Let’s look at some messy hair boys styles that will open up your options and help you find new ways to wear a mane that has a mind of its own. 

15 Messy Hair Boys’ Styles You Can Do in 5 Minutes or Less

Got 5 minutes to spare in the mornings? Make sure you do, because these trendy and messy hairstyles for boys take 5 minutes or less to pull off. Forget polished, prim, and proper looks.

Today, we’re focusing on the fun styles – the ones that are tousled, piece-y, and perfectly imperfect. Take a look at the most popular messy hair boys styles we’re seeing this year! 

Bendy Tousled Quiff

Messy styles for boys are a whole lot easier when you’ve got a little natural texture to work with. This boy has a very slight wave in his hair, which makes it the perfect candidate for a quiff hairstyle (much longer in the front).

Spray the hair with a little mousse for a lightweight texture boost and scrunch it up with your hands while it’s damp. 

Messy Two-Toned Two Block Cut

The two block haircut has two sections (blocks): Long on top and short around the bottom. Add to the drama by bleaching the top and mussing it up with plenty of texture. Try wax or pomade worked into the ends to get this messy, piece-y texture. 

Shaggy Pushed-Back Top

For a kid who likes to keep things shaggy, messy, and carefree, what better style than this pushed-back textured look? Even pin-straight hair can rock messy styles when you add the right kind of product.

Work a soft-hold gel or lightweight mousse through the hair and use your fingers to direct it toward the back. Pull up on the ends a little to get that boost in volume like you see here! 

Medium Messy Taper With Bangs

Tapered haircuts are great for kids, and this medium-length version is the perfect framework for a messy-on-purpose style. Starting off with wavy texture will create all the volume and texture this look needs.

Add a small amount of gel or mousse to your hands and work it through the hair on top, pulling the hair from the crown diagonally forward. Split the bangs and twist some of the ends with a little more mousse to define them. Done! 

Styled-Up Taper With Long Bangs

With a face this cute, who wouldn’t want to show it off? Lifting the bangs and styling them upward with gel keeps the hair out of his eyes and just so happens to be a trendy style for boys.

The haircut is a short taper that gradually shortens toward the neckline so the “mess” is contained to the top and front. This is a great option for younger boys! 

Jagged Layered Crop

You don’t have to create a messy look with only the texture in your hair. You can start the process by having your barber cut your bangs in a jagged, uneven line along with lots of short layers!

With the messiness built right into the cut, all you need to do it add a dollop of gel to your mane while it’s damp and “shake” your fingers through it to help it group up into thick, chunky pieces. Keep the sides and back neatly brushed for contrast. 

South of France Taper

The South of France haircut features some type of fade or taper around the ears so all the length is focused on the top and slightly down the sides. This high-volume look takes on a delightfully messy appearance with big, natural curls.

You don’t want them too perfect, so work a little curl cream through with your fingers and concentrate on defining and separating just a few pieces to keep the look casual. 

Side-Styled Pompadour Taper

The top of this style reminds us of a barrel wave crashing down as the hair gets lifted at the side part. The long top can be styled into a slicked-back pompadour haircut, but that’s not what we’re here for – it’s this awesome, mussed-up texture!

A slight wave in the hair allows it to flip out at the ends. Paired with the high-volume boost, this messy look is almost effortless but looks really nice for young boys and teens alike. 

Wayward Curly Quiff

If you have curly hair, you know that it tends to have a mind of its own. If your curls want to go wayward, let ‘em! This short haircut is longest in the front to create a quiff.

You don’t need to do anything but add a little gel or curl cream to the front, scrunch it up, and let it air dry or use a diffuser to blow dry. Bonus points for curls that do their own thing and point off in different directions!

Read Next: Curly Hair Men

Messy Textured Top

Texture is one of the easiest ways to pull off a messy hair boys style. If your hair has a little natural wave, a long-on-top style like this is perfect.

But even pin-straight hair can pull it off with the help of a little medium-hold gel! Work a nickel-sized amount of gel into damp hair and blow dry (use your fingers, not a comb) or air dry to nail this look. 

Mid Taper Fade With Pushed-Back Top

The key to pulling off this messy-inspired look is not using too much product. You want your hair’s natural texture to shine through so it creates gaps, bends, and imperfect lines.

Work a dime-sized amount of gel (better yet, mousse) through the hair on top and use your fingers to push it backward and slightly over to the side. If it looks too perfect, muss it up and spritz with water. 

Curly Crop With Split Bangs

Tousled curls pointing in different directions, tons of volume and body, and a face-framing split bang that opens up to show off the face all make for a cute messy style that any curly-haired boy will appreciate.

Soft layers in the cut and a lightweight curl cream will make it easier for curl groups to flip out at different levels to create this lovably messy look.

Fade With Disheveled Top

For a clean-cut yet messy style, opt for clean lines and a gradual length transition on the bottom. Leave the top long so it can be styled with a disheveled, tousled look. If you don’t like the wet look, try mousse instead of gel and diffuse the hair upside down for more volume.

Read Next: Fade Haircuts

High Undercut With Tousled Curls

A high undercut will give any boy a more grown-up look instantly, but it’s all balanced out with the long, curly top that is full of messy, tousled texture.

Big, loose curls work best for a style like this, but tighter curls can adopt the messy look with random definition achieved by applying curl cream to every other curl or random pieces that stick out. 

Spiked-Up Texture

Spiked-up texture is perfect for little wild ones – and older wild ones, too. With a firm-hold gel, it’s easy to mold the type of spikes you want into the hair.

Create skinny, uniform spikes for a more polished look or take the chaotic route and group the hair into random spikes of different sizes. Make sure everything is being directed upward and hit it with a little hairspray to prolong the hold! 

Things to Consider

Styling boys’ hair with a messy or tousled look takes a little practice to make perfect. After all, if you wanted a purely messy look, there’d be no styling required! What you need is a solid framework and foundation finished off with a fun, messy texture. 

Here’s what you need to know to make your messy hair boys styles turn out with just the right balance between disheveled and polished. 

• Get the right products for your hair. Mousse, gel, and hairspray are the most common products you’ll need to do a messy hairstyle for boys. Mousse is best for straight or fine hair that is easily weighed down. Gel works best for coarser hair or very curly strands. Choose the level of hold you need – for casual, messy styles, light to medium hold will work. For structured messy looks, firm-hold gel and hairspray are a must. Learn more here: Best Products for Curly Hair. 
• Creating a messy look is all about creating texture. If you have super straight hair, that means giving your locks a random pattern by pushing, brushing, or directing sections of your hair in different directions. For wavy or curly hair, allowing your hair to air dry with mousse or gel worked in should create a great textured base for any messy style. 
• Have “messy” built right into the cut. If you’re open to getting a new haircut, a barber can create the perfect framework for messy styles by cutting layers (short or long), leaving strategic length for tousled texture, and creating jagged, uneven lines that give even clean-cut styles a mussed-up look. Show your barber pictures of the types of styles you want to be able to create and they’ll be able to work a little messiness into the cut to make styling even easier. 
• A little product goes a long way. If you haven’t been using hair products regularly, there’s a good chance you’re going to use too much the first few times. Always err on the side of caution and use less than you think you need when it comes to gel, mousse, curl cream, etc. You don’t want to shellac your hair – just give it more shape, texture, and hold. If your hair feels crunchy or rock hard, you probably used too much. 
• Get a trim for a messy-on-purpose look. There’s a fine line between casual, carefree messy and actual messy. If you’re finding that your hair tends to look like you just woke up when you try to style it messy, you probably just need a trim. Too much grown-out length will add excess weight and volume where you don’t want it. A quick trim will revitalize your hair and make every messy-on-purpose style look better. 

Which Messy Hair Boy’s Style Will You Pick?

Messy hair boys’ styles are a long-lasting trend for a reason. They’re easy to style, flatter every face shape and hair type, and enable you to show off your natural texture without spending too much time styling. What’s not to love?

If you’re ready to loosen up and start sporting messy-on-purpose hairstyles, try any of the options on our list.

You’ll look more confident and develop a better relationship with your hair when you love the way it looks! Especially when you can make these styles happen in 5 minutes or less.   

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