Medium haircuts for boys offer the perfect balance between manageability and style. These versatile cuts are long enough to showcase personality while remaining easy to maintain. Whether your little man is heading to school, a formal event, or just hanging out with friends, there’s a medium-length style that’s perfect for the occasion. Let’s explore the top 20 medium haircuts that will keep your boy looking sharp and feeling confident.
1. Classic Side Part
The classic side part is a timeless medium haircut that exudes sophistication and charm. This style involves parting the hair on one side, typically where the hair naturally separates. The hair is kept longer on top, usually about 2-3 inches, while the sides are trimmed shorter but not buzzed.
To style, use a small amount of pomade or styling cream to smooth the hair and create a defined part. Comb the longer top section to one side, following the natural part line. This haircut is perfect for boys who need a polished look for school or formal events. It’s also versatile enough to be styled more casually by tousling the top for a relaxed appearance.
2. Textured Crop
The textured crop is a modern take on the classic short back and sides. This medium-length cut features a longer top with plenty of texture, while the sides are kept shorter for contrast. The top hair is usually cut with a point-cutting technique to create natural-looking texture and movement.
To style, apply a small amount of texturizing product to damp hair and use your fingers to tousle and lift the hair for a messy, lived-in look. This cut is ideal for boys who want a low-maintenance style that still looks edgy and contemporary. It’s perfect for casual outings and can be easily dressed up with a bit more styling for special occasions.
3. Surfer Shag
The surfer shag is all about embracing natural texture and movement. This medium-length cut features layers throughout, with the hair typically falling just above the shoulders. The layers are cut to enhance wave and curl, creating a carefree, beachy vibe.
Styling is minimal – simply apply a sea salt spray to damp hair and scrunch to enhance natural texture. Let it air dry for the most authentic look. This cut is perfect for boys with naturally wavy or curly hair who want a low-maintenance style that captures the laid-back surfer aesthetic.
4. Slicked Back Undercut
The slicked back undercut combines edgy and classic elements for a striking look. The sides and back are cut very short or buzzed, while the top is left long enough to slick back, typically 3-4 inches. This creates a dramatic contrast between the short sides and the longer top.
To style, apply a strong-hold pomade to damp hair and comb it straight back from the forehead to the crown. This look is bold and eye-catching, perfect for boys who want to make a statement. It’s versatile enough for both casual and formal settings, depending on how neatly it’s styled.
5. Messy Fringe
The messy fringe is a playful and youthful cut that works well for boys with straight to wavy hair. This style features a longer top section that’s cut into a fringe (bangs), while the sides are kept shorter but not too tight. The fringe is typically long enough to reach the eyebrows or just above.
Styling is simple – apply a light-hold product to damp hair and use your fingers to tousle the fringe forward and to the side for a casually disheveled look. This cut is perfect for boys who want a low-maintenance style with a bit of edge. It’s great for school and casual outings.
6. Faux Hawk
The faux hawk is a more wearable version of the classic mohawk. This medium-length cut features longer hair on top that’s gradually tapered shorter on the sides. The top hair is usually about 2-3 inches long, allowing it to be styled up and toward the center of the head.
To achieve the faux hawk look, apply a strong-hold gel or pomade to damp hair. Use your hands or a comb to style the hair up and towards the center, creating a ridge-like effect. This edgy style is perfect for boys who want to stand out and express their personality. It’s ideal for casual settings and can be toned down for more formal occasions.
7. Curtain Bangs
Curtain bangs have made a comeback in recent years, offering a soft, retro-inspired look. This medium-length cut features longer hair on top that’s parted down the middle, with the front sections cut to frame the face like curtains. The sides are usually kept a bit shorter for balance.
To style, apply a lightweight mousse to damp hair and blow-dry the bangs away from the face using a round brush. Once dry, use your fingers to gently separate the bangs and create a soft, face-framing effect. This cut is perfect for boys who want a softer, more romantic look. It works well for both casual and dressier occasions.
8. Layered Mid-Length
The layered mid-length cut is a versatile option that works well for various hair types and face shapes. This style features hair that falls around the ears or to the base of the neck, with layers cut throughout to add movement and reduce bulk.
Styling can vary depending on hair texture – for straight hair, a light styling cream and quick blow-dry can create a smooth, polished look. For wavy or curly hair, a curl-enhancing product and air-drying can bring out natural texture. This cut is perfect for boys who want a bit more length without the maintenance of truly long hair.
9. Quiff
The quiff is a classic style that’s been popular for decades. This medium-length cut features shorter sides and back, with longer hair on top, especially at the front. The front section is typically styled up and back for a voluminous look.
To style a quiff, apply a volumizing mousse to damp hair and blow-dry the front section up and back using a round brush. Finish with a light-hold hairspray to keep the style in place. This cut is perfect for boys who want a stylish, put-together look. It’s suitable for both casual and formal occasions.
10. Textured Pompadour
The textured pompadour is a modern take on the classic 1950s style. This cut features shorter sides and back with a longer top, similar to the quiff, but with more emphasis on height at the front. The key difference is the addition of texture throughout the top section.
To style, apply a texturizing product to damp hair and blow-dry the top section up and back, using your fingers to create texture. Finish with a matte clay or paste for added definition. This style is perfect for boys who want a bold, fashion-forward look. It’s ideal for special occasions or for making a statement in everyday settings.
11. Shaggy Layers
The shaggy layers cut is all about embracing natural texture and movement. This medium-length style features layers cut throughout the hair, with a slightly longer length on top and around the face. The overall effect is casual and effortlessly cool.
Styling is minimal – apply a texturizing spray to damp hair and either air dry or blow-dry with a diffuser attachment to enhance natural texture. This cut is perfect for boys with wavy or curly hair who want a low-maintenance style that looks intentionally messy. It’s great for casual, everyday wear.
12. Swept Back
The swept back style is a sophisticated option for boys who want a polished look. This medium-length cut features hair that’s long enough on top to be combed back, typically 3-4 inches, with shorter sides and back for contrast.
To style, apply a medium-hold gel or pomade to damp hair and comb it back from the forehead to the crown. Use a blow-dryer for a smoother finish, or let it air dry for a more relaxed look. This cut is perfect for boys who need a neat, put-together style for school or formal events.
13. Side-Swept Bangs
Side-swept bangs offer a soft, approachable look that works well with medium-length hair. This cut features longer hair on top that’s cut at an angle to create bangs that sweep across the forehead. The sides and back are typically kept shorter for balance.
To style, apply a light-hold product to damp hair and blow-dry the bangs to one side using a round brush. Finish with a light touch of hairspray to keep the bangs in place. This cut is perfect for boys who want a bit of length in front without the maintenance of full-length bangs. It’s versatile enough for both casual and dressier occasions.
14. Textured Taper
The textured taper combines the neat appearance of a taper cut with the modern edge of textured styling. This medium-length cut features a gradual taper on the sides and back, with longer, textured hair on top.
To style, apply a texturizing product to damp hair and use your fingers to tousle and lift the hair on top for a messy, lived-in look. This cut is perfect for boys who want a low-maintenance style that still looks intentional and stylish. It’s great for everyday wear and can be easily dressed up for special occasions.
15. Curly Top Fade
The curly top fade is an excellent option for boys with naturally curly hair. This style features a fade on the sides and back, with longer curls left on top. The contrast between the short sides and the voluminous top creates a striking look.
To style, apply a curl-enhancing cream to damp hair and either air dry or use a diffuser attachment on a hair dryer to enhance the natural curl pattern. This cut is perfect for boys who want to embrace their natural texture while keeping a neat, manageable style. It works well for both casual and dressier settings.
16. Modern Bowl Cut
The modern bowl cut is a updated version of the classic style. This medium-length cut features a rounded shape that follows the curve of the head, but with softer edges and more texture than its traditional counterpart. The hair is typically kept all one length around the sides and back, with some texturizing on top.
To style, apply a light-hold product to damp hair and either air dry or blow-dry for a smoother finish. Use your fingers to create some separation and texture on top. This cut is perfect for boys who want a unique, fashion-forward look. It’s ideal for casual settings and can make a statement at school or social events.
17. Textured French Crop
The textured French crop is a stylish and low-maintenance option. This cut features a short back and sides with a longer top that’s cut straight across the forehead. The key to this style is the added texture on top, which gives it a modern edge.
To style, apply a matte clay or paste to dry hair and use your fingers to create texture and lift on top. This cut is perfect for boys who want a neat, easy-to-manage style with a bit of edge. It’s suitable for both casual and semi-formal occasions.
18. Long Fringe with Taper
This style combines the edginess of a long fringe with the neatness of a tapered cut. The hair on top is left long enough to create a substantial fringe, while the sides and back are tapered for a clean look.
To style, apply a lightweight styling cream to damp hair and blow-dry the fringe forward and to the side. Use your fingers to create some separation for a piecey look. This cut is perfect for boys who want to make a statement with their hair while still maintaining a relatively neat appearance. It’s versatile enough for school, casual outings, and even dressier events.
19. Messy Mid-Part
The messy mid-part is a relaxed, effortless style that works well with medium-length hair. This cut features a center part with hair that falls to about chin length. Layers are cut throughout to add movement and reduce bulk.
Styling is minimal – apply a texturizing spray to damp hair and either air dry or blow-dry with a diffuser for added volume. Use your fingers to tousle the hair for a lived-in look. This cut is perfect for boys who want a low-maintenance style with a bit of rock-and-roll edge. It’s ideal for casual settings and can be easily dressed up with some styling for special occasions.
20. Brushed Up Texture
The brushed up texture style is a modern, edgy look that works well with medium-length hair. This cut features shorter sides and back with a longer top that’s styled upwards and backwards.
To achieve this look, apply a strong-hold product to damp hair and use a blow-dryer and brush to direct the hair up and back. Finish with a texturizing paste to create definition and hold. This cut is perfect for boys who want a bold, fashion-forward style. It’s great for making a statement at school or social events, and can be toned down for more formal occasions.
In conclusion, medium haircuts for boys offer a world of possibilities. From classic styles to modern edgy looks, there’s a cut to suit every personality and occasion. Remember, the key to a great haircut is not just in the style, but also in the maintenance. Regular trims and proper hair care will keep these medium-length cuts looking their best. Whether your boy prefers a neat and tidy look or something more relaxed and textured, these 20 styles provide plenty of inspiration for his next trip to the barber.