20 Medium-Length Teen Boy Haircuts

Medium-length haircuts for teen boys are a great way to combine style and convenience. These cuts offer versatility, allowing for various looks ranging from edgy to classic. Whether you’re aiming for a trendy style or something low-maintenance, there’s a medium-length haircut that will fit your personality and lifestyle. Let’s explore 20 fantastic medium-length haircuts that will elevate your teenage style.

1. The Textured Crop

The textured crop is a contemporary and edgy haircut that’s perfect for teens. The hair is kept slightly longer on top while the sides are tapered or faded. Texturing the top adds a modern, messy look.

With this cut, you can style it in various ways. For a relaxed vibe, you can add some hair product for texture. For a sharper look, use a comb to style the hair more neatly. This versatile cut works well for both casual and semi-formal occasions.

2. The Quiff

The quiff is a timeless classic that’s seen a resurgence in recent years. For a teen boy, the quiff involves longer hair on top styled backward and upwards, while the sides are usually kept short. It’s a stylish way to elevate any look.

A quiff can be combined with a fade or undercut to add even more flair. This haircut requires a bit of maintenance with regular styling using pomade or gel. It’s great for those who want a bold yet refined appearance.

3. The Pompadour

The pompadour is another timeless cut for teen boys. The hairstyle features voluminous hair on top that’s styled backward while keeping the sides short and neat. It’s an elegant choice for teens who enjoy a more polished look.

With this style, volume is key. Teens should use a blow dryer to lift the hair and a light-hold product to maintain the shape. This look is perfect for formal events or when a teen wants to stand out from the crowd.

4. The Bro Flow

The bro flow hairstyle is ideal for a laid-back, relaxed look. The hair is left longer on top and gradually flows into medium-length layers around the sides. It’s great for teens who prefer an effortless, natural style.

The flowy texture gives a youthful and carefree vibe. Styling this cut usually requires minimal effort. It can be worn messy or neatly styled, depending on the occasion. This haircut suits active teens who want something low-maintenance.

5. The Messy Fringe

The messy fringe is a fun and easy-going hairstyle perfect for teen boys with thick hair. The front part of the hair is cut into a fringe, and the overall style is kept tousled and textured for a natural, messy effect.

It’s a great option for teens who don’t want to spend much time styling their hair. A simple pomade or wax can help enhance the texture. The messy fringe works well for casual days and is very low-maintenance.

6. The Undercut with Pompadour

This version of the pompadour combines the classic volume with a sharp undercut on the sides. The top remains long enough to be styled back, while the sides are faded or shaved for a clean, edgy look.

The contrast between the long top and short sides creates a bold, modern style. Teens can use a blow dryer for volume and a strong-hold product to keep the pompadour intact. This haircut works well for those who want to make a fashion statement.

7. The Side Part

The side part is a classic medium-length haircut that’s both clean and sophisticated. The hair is parted to one side, with the rest of the hair styled neatly and uniformly. This look is versatile and can be customized to suit various hair textures.

For teens with straight hair, the side part works perfectly for a sharp, polished look. It can be worn with a slight wave or kept straight. It’s an easy-to-maintain haircut that suits both casual and formal settings.

8. The Wavy Shag

The wavy shag is ideal for teens with naturally wavy hair. The hair is cut into layers, with the longest strands at the top and shorter layers around the sides. This creates a carefree, voluminous look full of texture.

This hairstyle works great for a relaxed, beachy vibe. A little product can help enhance the waves and add definition to the layers. Teens with wavy hair will appreciate this low-maintenance cut that’s easy to manage and style.

9. The Buzz Cut Fade

The buzz cut fade is a bold, stylish haircut where the hair is kept short all around, with the sides gradually fading into the longer top. This clean-cut style offers a fresh, modern look with minimal upkeep.

For teens who prefer a hassle-free haircut, the buzz cut fade is ideal. The fade on the sides gives it a contemporary twist while maintaining a sharp and neat appearance. It’s the perfect blend of style and convenience.

10. The Classic Caesar Cut

The Caesar cut features short, evenly cut hair on top with a blunt fringe across the forehead. The sides are typically short, and the cut offers a neat, structured look. This is a classic and easy-to-maintain style.

The Caesar cut is great for teens who want a timeless, neat style that doesn’t require much effort. It can be styled with a bit of product to keep the fringe in place. This look works well for both school and casual outings.

11. The Curly Top

For teen boys with curly hair, the curly top is an excellent medium-length haircut. It allows curls to grow freely on top while keeping the sides trimmed short for a balanced appearance. This look celebrates the natural texture of the hair.

With this cut, curls are the star of the show. Teens with curly hair can use a curl-enhancing product to maintain definition. This style works well for those who want to embrace their natural texture while keeping things tidy on the sides.

12. The Ivy League

The Ivy League is a clean, polished haircut that combines a short back and sides with slightly longer hair on top. It’s a timeless, preppy style that works well for teens who prefer a smart, sophisticated appearance.

This cut can be styled neatly with a side part for a classic look or left with a little more texture for a more relaxed vibe. The Ivy League works well for various occasions, from school to formal events.

13. The Tapered Cut

The tapered cut features short sides that gradually lengthen toward the top of the head. It’s a versatile, low-maintenance haircut that gives a clean yet stylish appearance, perfect for teens who want something sleek and modern.

The tapered cut can be paired with different lengths on top, from short to medium. It requires minimal styling, but some light product can add texture. It’s a great choice for teens who want a tidy yet fashionable look.

14. The Faux Hawk

The faux hawk offers an edgy and daring look for teen boys. The hair on the top is styled upright and spiked, while the sides are either shaved or faded for a stark contrast. It’s a bold and attention-grabbing style.

For styling, teens can use hair gel or pomade to create volume and spikes. This cut works best for those with straight or slightly wavy hair. The faux hawk is ideal for teens who want to stand out and express their unique style.

15. The Slicked-Back Style

The slicked-back style is perfect for teen boys who want a more refined, sleek look. The hair is styled backward using a comb and some product to create a smooth, controlled appearance. This look works well for formal occasions.

To achieve the slicked-back style, teens should use a pomade or gel for a shiny finish. This classic style is timeless and offers an elegant look. It’s great for any teen looking for sophistication with minimal effort.

16. The Fringe with Undercut

The fringe with undercut combines the edgy appeal of an undercut with the softness of a front fringe. The top part of the hair is left longer and styled forward to form the fringe, while the sides are shaved or faded.

This style works well for teens who want a bold, unique look. The combination of a short undercut with the long fringe creates a striking contrast. It’s perfect for teens who want something modern and easy to maintain.

17. The Layered Cut

A layered cut is a versatile and timeless hairstyle for teens. The hair is cut in layers to add volume and texture. The length can vary depending on the desired style, but medium-length layers work best for most teens.

Layering adds dimension to the hair, making it easier to style. Teens can use a bit of product to emphasize the layers or wear it natural. This cut is perfect for those who want flexibility in their hairstyle.

18. The Bro Flow with Undercut

This variation of the bro flow adds an undercut to the look. While the top is kept long and flowing, the sides are shaved or faded for a more dramatic contrast. It’s an ideal cut for teens who want a laid-back yet trendy appearance.

The undercut adds an edge to the typically relaxed bro flow, making it suitable for those who want something more modern. Styling is easy, and teens can choose to wear it messy or more polished. It’s great for active, trendy teens.

19. The Long Shag

The long shag is a great option for teens who prefer longer hair with some texture. The hair is cut into layers that vary in length, creating a voluminous, shaggy appearance. It’s perfect for teens who love a relaxed, grungy look.

This style works particularly well with wavy or curly hair. Some texturizing spray can help enhance the shaggy look and make it easier to style. It’s a low-maintenance, cool hairstyle for teens who want to embrace a carefree vibe.

20. The Broccoli Cut

The broccoli cut is a fun, modern haircut where the hair is cut into a rounded shape on top, resembling a head of broccoli. The sides are usually short, with the top left fuller for a quirky, youthful style.

This playful cut is perfect for teen boys who enjoy standing out. It’s easy to maintain with some regular trims to keep the shape intact. With the right styling products, this unique haircut can be transformed into a signature look.


These 20 medium-length teen boy haircuts cover a wide range of styles, from edgy to sophisticated. Whether you’re looking for something easy to manage or ready to try a bold look, these cuts offer versatility for any teen. Experimenting with different styles is a great way to express individuality and personality!

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