10 Cooler Than Ever Teen Boy Haircuts

by Updated on April 24, 2018

In the 90s, life was all about experimenting with hair. Within a short space of time, I myself went from dreamboat flat top to chin-length – and even kriss-kross cornrows (don’t judge me here, please!). But today’s teen boy haircuts seem to have entered a new era of sophisticated.

Shorter sides, longer tops are taking the world by storm as we speak. It’s about the fade and the undercut. The contrast between different lengths – and the carefree ‘I’m kind of a bad boy’ vibe.

The good news is that, the ‘short sides long top’ hairstyles are extremely versatile and will work on pretty much any imaginable hair type. Curly, wavy, straight, thick, thin – whatever type of hair you’ve been given, you will pull it off!

The only problem is that, there are tons of teen boy haircuts to choose from. But don’t fret – you won’t have to spend hours scrolling through Instagram photos desperate to get inspired, because we have some ultimate favorites we’re going to share. Let’s check out these 10 coolest teen boy haircuts that are thriving right now. And – let me tell you this…these are definitely too cool for school.

#1: Cool Mid-Fade + Sharp Design

If you’ve got medium length hair and are looking for a trendy and sleek hairstyle to experiment with, this is a look to seriously consider. The sharp design on the sides makes the look stand out, while mid-fade works to create a contrast between the long hair on the top and the short, tapered sides. To achieve the look, you’ll want to make sure you have some strong-hold pomade at hand.

Cool Mid-Fade
Cool Mid-Fade + Sharp Design

#2: Undercut With Colour + Tapered Sides

Now, we don’t think we’ve seen anything cooler than this for a while – have you? We absolutely dig this quirky, sharp and trendy hairstyle – especially the coloured ends! Whichever colour you go for, it’s going to be a definite head-turner. To achieve the textured look, go for a dash of medium-hold pomade.

Undercut With Colour
Undercut With Colour + Tapered Sides

#3: Medium Length Undercut + Mid-Fade

Now, if you’re lucky and have lots of hair, then you may want to try this awesome, big hairstyle for medium-length locks. The best news is that the hairstyle won’t require much styling. You can just chuck a bit of medium-hold pomade on before running out the door – and you’re good to go!

Medium Length Undercut + Mid-Fade
Medium Length Undercut + Mid-Fade

#4: Mid-Fade + Side Combover

Check out this sleek hairstyle – and tell me it’s not perfect for mid-length hair! How does one style a combover, you wonder? Start with fresh, clean hair and use a blow dryer to create more volume. Take a dime-sized amount of styling cream (casual, relaxed look) or pomade (for more shine and stronger hold), working it into the hair from the roots. If you’re after a clean part, then you’ll want to comb lengthwise starting from the back of your head to your forehead. And – you’re good to go!

Mid-Fade + Side Combover
Mid-Fade + Side Combover

#5: Voluminous Quiff + Tapered Sides

“Wow – check out that quiff!” That’s exactly the reaction you’ll achieve with this stand-out hairstyle. We’re definitely fans of the smooth effect – for that you’ll want to use a smoothing cream or anti-frizz serum (unless you were born under a lucky star and frizz isn’t part of your daily battles). Plus, the sides have been tapered rather than faded, which works perfectly since the hair colour on top already contrasts with the sides.

Voluminous Quiff + Tapered Sides
Voluminous Quiff + Tapered Sides

#6: High Fade Undercut + Zig Zag Detail

If a standard fade doesn’t float your boat, you may want to try something a little more daring. How about a unique fade design, such as this zig zag detail? The good thing is that you and your barber can get as creative with these as you like, making it a haircut no-one else will have!

High Fade Undercut + Zig Zag Detail
High Fade Undercut + Zig Zag Detail

#7: Mid-Fade Undercut + Pompadour

You know why we’re into a good pompadour so much? Because it is one of those hairstyles that’s simply timeless. Boys were crazy about it in the 60s – boys are crazy about it now. Of course, the pompadour has gone through the process of modernisation, but in essence, it remains the same. Big, voluminous hair that turns heads!

Mid-Fade Undercut + Pompadour
Mid-Fade Undercut + Pompadour

#8:Messy Undercut + Skin Fade

If you’re not that into neat and tidy, then this awesome spiky undercut with skin fade will be the right choice for you. It’s a statement hairstyle, that’s a lot edgier than the classy combover or a quiff. Plus, styling it won’t be a mission – some strong pomade will achieve the spiky textured look you’re after, without having to spend hours in front of the mirror blow drying and combing.

Messy Undercut + Skin Fade
Messy Undercut + Skin Fade

#9: Mid-Fade Undercut for Curly Hair

Now – what did we say about the undercut being the most versatile hairstyle there is? If you didn’t believe us, here’s your proof! We’re used to seeing an undercut on straight hair most often, but even if you have afro hair or curls, you can still achieve an uber cool undercut hairstyle. Maybe one that’s even more unique… Especially if you add a design detail like this one!

Mid-Fade Undercut for Curly Hair
Mid-Fade Undercut for Curly Hair

#10: Volume and Texture + Fade and Design

And now *drumroll*… We’ve saved the best for last! Here’s a hairstyle that says ‘Don’t mess with me. My hairdo is flippin’ awesome!’. There’s a ton of things we’re fans of here – from the volume to the dyed ends. Oh – and the texture deserves a round of applause. Sure, there’s a lot going on here – but if you’re someone who likes standing out a little more, this hairstyle may be just the right thing for you.

Volume and Texture + Fade and Design
Volume and Texture + Fade and Design

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