30 Trendy Medium Length Hairstyle for Boys

Looking for a fresh cut that’s not too short and not too long? Medium length hairstyles for boys strike the perfect balance between style and ease. Whether you want a laid-back look or a trendsetting vibe, these hairstyles work for school, weekends, and everything in between.

At Hairstyle Inspirations, we’ve gathered the coolest medium cuts that combine personality with practicality. From layered waves to textured shags, you’ll find the perfect look to match your style. Let’s explore 40 stylish options that are bold, modern, and totally on-trend.

1. Textured Fringe with Faded Sides

This style brings volume and personality with a choppy, textured fringe while keeping the sides clean with a subtle fade. It’s a go-to look for boys who want movement on top without too much mess. Great for straight or slightly wavy hair. Easy to style and always looks trendy.

2. Classic Medium Taper Cut

Timeless and neat, the classic taper cut offers structure without sacrificing length. The hair is left medium on top with gentle tapering around the sides and back. It’s a versatile option that works for school or special occasions, making it one of the most polished medium length hairstyles for boys.

3. Medium Shag with Natural Waves

Let those natural waves shine with a medium shag. The cut layers the hair all around for added volume and movement. It’s effortlessly cool and works best with textured or wavy hair. Ideal for boys who love a laid-back, surfer-inspired style with minimal styling effort required.

4. Curtain Bangs with Tapered Edges

Curtain bangs are back and better than ever. This look features longer hair in the front parted down the middle, paired with neatly tapered sides. It frames the face while adding flair to any casual outfit. A popular medium length hairstyle for boys with a love for 90s vibes.

5. Modern Mop Top

The modern mop top gives off major artistic energy. Slightly longer all over with volume on top and light layering, this style keeps the look soft and youthful. It’s ideal for boys who want a bold yet approachable hairstyle that turns heads without needing sharp lines or fades.

6. Medium Bro Flow

The bro flow is perfect for boys growing their hair out. It flows naturally back from the forehead, with hair resting just above the ears and neck. It’s low-maintenance and full of character. One of the most laid-back medium length hairstyles for boys who like a cool, easygoing look.

7. Layered Side Part

Add sophistication with a layered side part. Hair is medium-length with layers that create volume and movement, parted cleanly to one side. This look can be dressed up or down and works especially well for boys with thicker hair who want something structured without looking too grown-up.

8. Windswept Medium Cut

This hairstyle looks like you just stepped off the beach. The windswept cut features textured, tousled strands that flow naturally. It’s great for medium hair that has a bit of body or wave. Perfect for carefree boys who love stylish messiness with a touch of charm and confidence.

9. Messy Layered Crop

A messy layered crop embraces organized chaos. Hair is left medium in length with choppy, uneven layers for texture. It’s meant to be styled with fingers and a bit of product to highlight the volume. A perfect fit for creative boys who like their look a little wild.

10. Medium Undercut with Volume

Combine a clean undercut with medium length on top for a dramatic contrast. The longer top can be slicked back, spiked up, or left messy. It’s one of the most daring medium length hairstyles for boys who want to show off their confidence and cool attitude with every look.

11. Medium Pompadour Fade

Add height with a medium pompadour and complement it with a fade for sharp contrast. This style gives boys a modern edge while still keeping that classic rockabilly vibe. Great for events or just making a strong impression at school. Use a pomade or styling cream for maximum hold.

12. Feathered Middle Part

The feathered middle part is soft and flowing, with layers that naturally curve away from the face. It’s great for boys who want a gentle, stylish frame without going too bold. This hairstyle works beautifully on straight or slightly wavy hair, giving off calm, composed, and confident vibes.

13. Thick Brush-Up with Taper

This style uses the natural thickness of the hair to create a full brush-up look. Hair is left medium on top and gradually tapered on the sides. It’s easy to style and delivers volume without the need for frequent trims. Ideal for boys who want a strong, trendy silhouette.

14. Medium Caesar Cut

The Caesar cut gets a medium-length upgrade. Hair is cut evenly all around but left longer than the traditional version. It frames the forehead and emphasizes natural texture. Great for boys with straight or slightly wavy hair who want a clean but noticeable look with just a bit of edge.

15. Soft Curls with Defined Layers

Celebrate curls with medium-length defined layers. This hairstyle adds bounce, shape, and personality without being overwhelming. A curl cream helps maintain the texture while reducing frizz. It’s one of the best medium length hairstyles for boys who want to embrace their natural curls with style and confidence.

16. Tousled Fringe with Razor Texture

A tousled fringe with razor-cut layers gives a rockstar edge. This style is great for thick, straight, or wavy hair and requires only minimal styling. The razor technique adds visual interest and movement. It’s a perfect pick for boys looking for a cool, artistic, and lived-in appearance.

17. Blunt Cut Bob for Boys

The blunt cut bob is bold and fashion-forward. Hair is kept at one length all around, usually just below the ears. It’s sleek, eye-catching, and perfect for boys who love a modern minimalist vibe. Ideal for straight hair types and those who enjoy standing out from the crowd.

18. Swept Back Medium Waves

This hairstyle takes advantage of natural waves and pushes them back away from the face. It creates a soft, elegant profile while still being laid-back. It’s a smart choice for boys who want a casual yet stylish look that’s quick to style and works for every setting.

19. Medium-Length Faux Hawk

The faux hawk isn’t just for short hair. This medium version keeps longer lengths on top, styled into a peak while the sides are faded or slightly tapered. It’s edgy but not extreme, making it one of the most stylish medium length hairstyles for boys who love bold fashion choices.

20. Medium Layers with Highlights

Add a pop of personality with medium layers paired with subtle highlights. This combo brings dimension and shine to the hair, making it look fuller and more dynamic. Perfect for boys who want something different without going overboard, and it works great with both straight and wavy textures.

21. Medium Afro Curls

Celebrate natural texture with a medium afro style. It offers volume, shape, and personality while being easy to maintain with the right care. This look embraces the natural curl pattern and is one of the most iconic medium length hairstyles for boys with coily or tightly curled hair.

22. Slicked Back Medium Hair

A sleek, brushed-back style delivers maximum confidence. With medium-length hair combed back using gel or pomade, this look works for formal or everyday wear. It’s neat, mature, and ideal for boys who like a put-together appearance without compromising on the cool factor. Think classic movie star with a twist.

23. Medium Curtain Undercut

Combine two trends—curtain bangs and an undercut—for a stylish contrast. The top is left longer and parted down the middle, while the sides are clipped short for definition. It’s edgy, modern, and one of the most fashion-forward medium length hairstyles for boys who want a unique statement.

24. Spiky Medium Top with Fade

This hairstyle adds energy with a spiky top that stands out. Hair is left medium on top to give room for texture and lift, while the sides are faded for a clean finish. A styling gel or wax helps keep everything in place. It’s bold, sporty, and super stylish.

25. Surfer-Inspired Beach Waves

Capture the carefree beach vibe with tousled, salt-sprayed waves. This hairstyle is perfect for medium-length hair that has a natural wave. Use sea salt spray to add texture and give it that sun-kissed, effortless finish. Great for boys who love an adventurous, outdoorsy aesthetic all year round.

26. Medium Mohawk with Tapered Sides

The mohawk gets a medium-length makeover in this stylish cut. Hair is longer in the center and gradually fades down the sides for a softer look. It’s one of the boldest medium length hairstyles for boys and works great with textured hair and confident personalities.

27. Bowl Cut with a Twist

The updated bowl cut features cleaner edges, subtle layers, and modern styling. Hair falls evenly around the head, but the added texture gives it a more contemporary feel. It’s quirky yet cool—a great choice for boys who like retro styles with a fresh new spin.

28. Medium Spiked Quiff

A spiked quiff adds drama and dimension to medium hair. This style lifts the front and adds layers for volume, giving it a structured yet stylish look. Perfect for special occasions or everyday flair, this hairstyle is a bold pick for boys who want to stand tall and stylish.

29. Tucked Behind the Ear Look

With medium-length hair, tucking behind the ear becomes a simple style statement. This look is especially great for boys with straight or layered hair and gives a sleek, slightly mysterious vibe. It’s perfect for laid-back personalities who want a bit of edge without too much styling effort.

30. Soft Mullet Revival

The mullet is making a subtle comeback and this medium version keeps it stylish. Shorter in the front and sides, with extra length at the back, the look is all about balancing edge and softness. It’s perfect for boys who want something different and bold with a retro twist.

Conclusion

Medium length hairstyles for boys are more than just a phase they’re a movement toward confident, expressive style. From classic layers to edgy fades, these looks prove you don’t need long locks to stand out.

With the right haircut, any boy can turn heads for all the right reasons. At Hairstyle Inspirations, we believe in finding a style that fits both your face and your vibe. Try one of these trendy ideas and let your hair do the talking!