25 Cool Medium Long Hairstyles for Teenage Guys

When it comes to hairstyles, teenage guys often find themselves searching for that perfect balance between trendy and low-maintenance. One of the best options out there? Medium long hairstyles. These styles offer the versatility of longer hair without the overwhelming upkeep, and they allow for endless customization depending on your vibe. Whether you’re rocking wavy locks, straight hair, or thick curls, there’s a medium long hairstyle to match your look and personality.

In this guide, we’ll dive into 25 incredible medium long hairstyles for teenage guys. From effortlessly cool shaggy layers to edgy mullets and sleek side parts, these styles will help you stand out while keeping things easy and fresh.

A collage of six teenage boys with different medium to long hairstyles. — Explore 25 cool medium long hairstyles for teenage guys at stylenessentials.com.

Why Medium Long Hairstyles Are Perfect for Teenage Guys?

Medium long hairstyles hit that sweet spot between short and long, giving you the best of both worlds. They’re versatile, stylish, and work well with virtually any hair texture. Plus, this length gives teenage guys the chance to experiment with different styles—whether you want to slick it back for a formal occasion, tousle it for a laid-back look, or try out bold layers for added dimension.

Here’s another bonus: medium long haircuts are adaptable. They work for school, sports, hanging out with friends, or even date night. So, if you’re tired of the same old short buzz cut or struggling to manage super-long hair, this might just be your perfect middle ground. Now, let’s dive into the styles!

1. The Messy Shag

Messy, carefree, and effortlessly cool—the shag is perfect for teenage guys who want a low-maintenance style that still looks trendy. This cut features layers throughout the hair, adding texture and movement. You can rock this style with natural waves, curls, or straight hair. A little sea salt spray will help you achieve that laid-back, “just rolled out of bed” look.

Person wearing a gray hoodie, black t-shirt, and ripped jeans. — The Messy Shag

2. The Bro Flow

Looking for a hairstyle that’s casual yet sophisticated? The bro flow is your answer. This style allows your hair to grow naturally, falling back and away from your face. It’s a great choice for guys with medium long hair who want a polished look without too much effort. Perfect for thick or wavy hair, the bro flow exudes confidence and maturity while still being youthful.

Person sitting at a wooden counter in a café, holding a white coffee cup, dressed in a blue plaid shirt over a white t-shirt and jeans. — Enjoying a cozy moment at the café with a warm cup of coffee.

3. The Wavy Side Part

The wavy side part is a timeless classic that suits almost every face shape. For teenage guys with medium long hair, this style offers a polished, clean look with a touch of elegance. The side part helps to frame your face while the waves add texture and dimension. Simply comb one side back, apply some light hold product, and let the waves do their thing.

Person wearing a white dress shirt with rolled-up sleeves and a gray patterned tie, with a blurred face. — The Wavy Side Part

4. The Textured Fringe

Fringe hairstyles have been trending for years, and for good reason. The textured fringe combines medium long layers with a messy, forward-swept fringe that falls just above the eyebrows. It’s a great style for teenage guys who want a modern, edgy look. Use a lightweight styling cream or pomade to define the layers and keep the fringe in place.

Person sitting on the ground with a skateboard, wearing a black t-shirt, gray jeans, white socks, and black and white sneakers. — The Textured Fringe

5. The Curtain Bangs

Curtain bangs are making a big comeback, and teenage guys are loving the vibe. This style features a center-parted fringe that frames the face, creating a relaxed and slightly retro look. Curtain bangs work particularly well with medium long hair, as they balance out the length and add a unique focal point.

Person leaning against a brick wall, wearing a denim jacket over a gray hoodie. — Casual urban style: a person in a denim jacket and gray hoodie against a brick wall.

6. The Classic Mullet

Love it or hate it, the mullet is here to stay! This retro-inspired style has been given a modern twist and is now one of the coolest medium long hairstyles for teenage guys. It features shorter hair on the sides and longer hair in the back, making it perfect for guys who want to stand out.

Person with long, wavy hair wearing a white T-shirt with a colorful graphic design of a skull and the text "GRATEFUL DEAD." — Enjoying a vibrant festival atmosphere in a Grateful Dead T-shirt.

7. The Tapered Afro

For teenage guys with natural curls or coils, the tapered afro is a bold and stylish choice. This medium long hairstyle keeps the sides shorter while leaving the top full and voluminous. It’s a great way to showcase your natural texture while keeping the overall look clean and fresh.

Person walking on a city street wearing a blue bomber jacket, orange sweater, and ripped blue jeans. — Urban street fashion: a person in a blue bomber jacket and ripped jeans.

8. The Surfer Hair

Channel your inner beach bum with this effortlessly cool style. Surfer hair is all about natural waves, loose curls, and a slightly tousled finish. This medium long hairstyle is perfect for teenage guys who want a laid-back, sun-kissed vibe, even if they’re miles away from the ocean.

Person with long, blonde hair walking on a beach while holding a surfboard. — Enjoying a sunny day at the beach with a surfboard.

9. The Layered Lob

The lob, or long bob, isn’t just for women—it’s a great unisex cut that works wonders for teenage guys too. This style features long layers that sit just above the shoulders, adding texture and movement. It’s ideal for guys with straight or wavy hair who want a sophisticated, yet casual look.

Person standing in an art gallery wearing a black turtleneck sweater and dark pants, with a blurred face. — Exploring monochromatic art in a well-lit gallery.

10. The Slick Back

For a sleek, polished look, you can’t go wrong with the slick back. This medium long hairstyle involves combing the hair straight back and using a styling product like pomade or gel to hold it in place. It’s perfect for formal occasions or when you want to switch things up from your everyday style.

Person wearing a formal outfit consisting of a grey suit jacket, white dress shirt, black tie, and black pocket square. — A well-dressed individual in a grey suit jacket and black tie in an outdoor setting

11. The Modern Quiff

The quiff has been a favorite among teenage guys for years. With medium long hair, you can give this classic style a modern twist by adding volume and texture at the front. Blow-dry the hair upwards, apply some pomade, and you’re good to go!

Person sitting on a bicycle on a dirt road, wearing a blue and orange jacket with a letter "A," a white t-shirt, black pants, and white sneakers. — Casual bike ride on a sunny day.

12. The Half-Up, Half-Down

For teenage guys with longer medium hair, the half-up, half-down style is a great way to keep hair out of your face while still showing off your length. This style works especially well with wavy or curly hair and is perfect for a casual, laid-back vibe.

Person walking outdoors on a paved pathway surrounded by trees, wearing a black zip-up hoodie, light gray t-shirt, black jogger pants, and white sneakers. — A casual stroll in the park on a serene day.

13. The French Crop

The French crop combines a short back and sides with a longer top that’s swept forward. It’s one of the more low-maintenance medium long hairstyles for teenage guys and works well for both straight and wavy hair. The texture on top gives it a modern, stylish edge.

Person sitting in a modern café, wearing a light gray sweatshirt, dark blue jeans, and white sneakers. — Enjoying a cozy moment in a modern café.

14. The Straight Side Sweep

For teenage guys with naturally straight hair, the side sweep is a simple yet effective style. Just comb your medium long hair to one side and use a light-hold styling product to keep it in place. This is a versatile look that works for both casual and formal settings.

Person sitting on concrete stairs, holding an open book, wearing a light blue button-up shirt over a dark shirt and dark pants. — Reading outdoors on a set of concrete stairs.

15. The Shaggy Mullet

A modern twist on the classic mullet, the shaggy mullet adds layers and texture for a more laid-back, rockstar vibe. This style is perfect for teenage guys who want a bold, statement-making haircut that still feels fun and youthful.

Person skateboarding at a skate park, wearing a gray hoodie, black pants, and white sneakers. — Performing a skateboard trick at the skate park.

16. The Curly Mop Top

For guys with natural curls, the curly mop top is a medium long hairstyle that celebrates texture and volume. This style keeps the curls loose and natural while offering a bit of structure with a subtle trim around the edges.

Person sitting on a bench outdoors, wearing a white T-shirt with a printed image, green pants, white socks, and white sneakers. — Casual day in the park with a unique printed T-shirt.

17. The Undercut with Long Top

The undercut is a versatile hairstyle that pairs perfectly with medium long hair on top. By keeping the sides and back short, you can emphasize the length and texture of the top. This style works great with straight, wavy, or curly hair and allows for tons of creative styling options.

Person standing in the middle of a city street, wearing a black leather jacket, white t-shirt, black ripped jeans, and black shoes. — Urban style: a person in a black leather jacket and ripped jeans standing in the city.

18. The Samurai Bun

Looking for something bold? Try the samurai bun. This style involves gathering your medium long hair into a high bun at the crown of your head. It’s a unique, eye-catching look that works best for guys with thick or straight hair.

Person with long, dark hair styled in a top knot, wearing a traditional black and white robe. — Traditional East Asian attire with a distinctive top knot hairstyle.

19. The Wavy Lob with Side Part

This style is perfect for teenage guys with medium long hair who want a polished but casual look. The wavy lob with a side part adds texture and dimension, making it a versatile style that can be worn anywhere.

Person sitting on a railing by the ocean, wearing a gray cardigan over a white t-shirt and denim shorts. — Enjoying a serene moment by the ocean at sunset.

20. The Brushed-Back Waves

For an effortlessly cool look, try brushing back your waves. This medium long hairstyle is great for teenage guys with naturally wavy hair, offering a relaxed yet stylish finish.

Person standing outdoors in a natural setting, wearing a blue denim jacket over a white t-shirt and black pants. — Casual and stylish: a person in a denim jacket enjoying the golden hour outdoors.

21. The Disconnected Undercut

The disconnected undercut is a great choice if you’re looking for a bold, edgy look. This style features shaved sides starkly contrasting to the medium long hair on top. The top can be styled in various ways—slicked back, left messy, or even paired with a quiff. It’s a striking, modern hairstyle that’s perfect for teenage guys who want to stand out.

Person wearing a black leather jacket and a white t-shirt. — Stylish in black leather: a person at a social gathering.

22. The Soft Waves with Center Part

Soft waves paired with a center part are a simple yet stylish choice for teenage guys. This hairstyle works beautifully with medium long hair, adding just the right amount of texture and flow. The center part gives a symmetrical, laid-back vibe that works for both casual hangouts and more formal occasions.

Person sitting on the floor in front of a bookshelf, reading a book. — Immersed in a good book in a cozy library setting.

23. The High Volume Pompadour

The pompadour is a classic that never goes out of style, and with medium long hair, you can turn up the volume. This version of the pompadour features a high lift at the front, with the rest of the hair slicked back or to the side. Use a strong-hold product to keep the height intact throughout the day. It’s a bold, stylish choice for teenage guys who love a polished look.

Person standing in front of a bathroom vanity with a large mirror surrounded by lights, wearing a grey blazer over a black shirt. — Getting ready for an event in a well-lit dressing room.

24. The Modern Caesar Cut

The Caesar cut gets a modern update by incorporating medium long hair with textured layers. This style keeps the hair slightly longer on top, brushed forward to create a clean, angular look. It’s a great choice for teenage guys looking for something trendy yet easy to maintain.

Person standing outdoors in an urban setting, wearing a black blazer over a white t-shirt and black pants. — Casual yet stylish: a person in a black blazer and white t-shirt in an urban setting.

25. The Windswept Look

The windswept look is ideal for guys who love a natural, carefree vibe. This style works best with medium long hair that has some natural wave or curl. Simply use your fingers to tousle the hair with a light styling cream, and let it fall naturally. It’s effortless and looks great in any casual setting.

Person with long, wavy hair wearing a grey hoodie and a backpack. — Enjoying a windy day in the hills.

Styling Tips for Medium-Long Hairstyles for Teenage Guys

No matter which style you choose, a few key tips can help you keep your medium long hairstyle looking its best:

Use the Right Products: Choose products that match your hair type. For instance, use lightweight creams for fine hair and stronger pomades or gels for thicker hair.
Embrace Texture: Don’t shy away from natural texture. Products like sea salt spray can enhance waves and curls for a more dynamic look.
Regular Trims: To maintain the shape of your haircut and avoid split ends, visit your barber or stylist every 6-8 weeks.
Experiment with Parting: Changing up your part can completely transform your look. Try a center part, side part, or even no part for different styles.
Invest in Good Tools: A quality hairdryer and comb can make all the difference when it comes to achieving your desired look.

Final Thoughts

Medium long hairstyles for teenage guys offer the perfect combination of style, versatility, and personality. Whether you’re aiming for a laid-back surfer look, a polished slick-back, or something bold like a modern mullet, there’s a medium-long hairstyle that fits your vibe. The best part? These hairstyles allow you to switch things up depending on your mood or occasion.

So go ahead—experiment, have fun, and find the style that makes you feel confident and ready to take on the world. After all, your hair is an extension of your personality, and with the right medium-long hairstyle, you can let it speak volumes!

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