The medium-length undercut is a stylish and versatile choice for men, offering freedom to experiment with various looks.

Whether you prefer a messy or slicked-back style, this haircut gives you a balance of edgy flair and comfort. It’s perfect for those wanting a casual, yet snazzy appearance while staying on top of fashion trends.

Best Medium-Length Undercut for Men: 50 Trendy and Versatile Looks

1. Textured Messy Quiff

Young man with a textured messy quiff hairstyle wearing a black shirt in a romantic city light background

For a stylish and bold look, keep the top longer while trimming the sides and back to about half inch. Use pomade for hold and style the hair back and to the side for a controlled finish. This cut gives flexibility and can be adjusted to fit your personal look without going too short.

2. Spiky Low Fade

Teenage boy with spiky low fade haircut styled with pomade sitting in garden with romantic background

Keep your hair around a few inches long. After air drying, apply pomade and pull hair straight up to form spikes. This simple method gives a textured, bold appearance.

3. Brushed Back Cut with Clean Edges

Photo of a boy with brushed back cut and clean edges hairstyle sitting outdoors with romantic background and confident smile

A modern look comes from clean edges and a smooth back finish, with a tapered touch at the nape. It suits medium-length hair well, whether kept neat or worn a bit messy, making it look great for any occasion.

4. Haircut with Elongated Swoopy Fringe

Teen boy with layered elongated swoopy fringe haircut styled with flip ends, in a romantic outdoor golden-hour background

For a relaxed yet stylish look, use a round brush while blow drying your hair to create a barely-there flip at the ends. Growing your hair out helps achieve texture and layers, giving it that effortless vibe. Avoid air drying for the best results.

5. Side-Shaved Chin-Length Comb Over

Rugged boy with chin-length comb over and shaved sides wearing black shirt in romantic sunset background

Pair a buzzed side with a thick beard for a rugged look. It’s important to be familiar with your barber or stylist’s work before getting this haircut, as it’s easy to make mistakes. Keep the sides neat while ensuring the top has enough length for a masculine vibe.

6. Fade Sides and Tousled Top Cut

Realistic photo of a boy with fade sides and tousled top haircut, styled with texture and subtle dark brown highlights in soft light

The sides are kept short while the top is styled with product to create texture and waves. A skilled hairstylist can balance the lengths for a sharp look, with highlights adding subtle depth.

7. Undercut Gelled Hairstyle

Young man with undercut gelled hairstyle and clean finish in romantic outdoor background scene

If you want a stylish look, adding some product can give it a natural finish without being overly stiff. Pairing it with a clean finish can elevate the style. Even if your hair isn’t the right length yet, you can still rock this look by embracing extra fullness while it grows.

8. Side-Parted Cut with Wavy Top

Young man with side-parted wavy haircut showing natural volume clean sides and relaxed confident expression in romantic setting

The natural style gives fullness and movement. The contrast between the top and sides makes the look sharp yet effortless, perfect for showing off your natural style with a clean finish.

9. Off-Centered Tapered Cut

Real photo of a boy with an off-centered tapered haircut in a romantic setting showing relaxed bold hairstyle

The style offers a fresh, touchable feel. It moves away from the usual spiked, hard hairstyles, giving a relaxed, casual vibe. The result is a confident, bold, and contemporary style that feels carefree and effortless.

10. Taper Cut with Pomp Top

Stylish boy with taper cut and pomp top hairstyle in a romantic outdoor scene at dusk

Try a mid-length hairstyle on top. This combination of contrasting lengths and colors creates a powerful yet classy style, with the top styled for extra volume. It’s the perfect balance of edgy and refined.

11. Taper Fade with Asymmetric Volume

Young man with taper fade and asymmetric volume haircut, clean beard, white shirt, in romantic outdoor light

The tapered edges and neat lines, along with volume, create a clean look. Blow drying is essential to achieve the right height, while the beard adds a rugged touch. It requires time and technique to perfect, creating a refined finish.

12. Pompadour with Short Sides

Young man with pompadour and short sides haircut in romantic setting wearing white T-shirt and black jeans

The medium-length with short sides creates a sharp contrast. The top gives volume, while the short sides enhance the shape. Using wax gives a strong hold, keeping it messy. The cropped exterior and skin fade work together, improving bone structure and making styling easier.

13. Slicked Back Cut with a Taper

Boy with slicked back cut and taper hairstyle wearing white shirt in soft romantic sunset background looking confident

For a sharp, clean look, the sides and nape taper seamlessly into a longer top. The hair is swept from the forehead in a smooth, classic shape. Adding pomade gives a vintage sheen and helps keep the style dapper and in place all day.

14. Shaved Side with a Carved Design

Teen boy with black hair in a shaved side carved design haircut wearing white tee outdoors at sunset

The hairstyle can transform with an artistic touch. The pattern can be placed between two different lengths, drawing attention to the overall shape, and can be emphasized or covered by adjusting the length, either brushing it away or combing it over.

15. Undercut with a Long Tousled Top

Realistic photo of boy with undercut and tousled top, brushed back with wax, set in a romantic cobblestone street at golden hour

Brushing the strands up and back adds sleek shape to medium length hair, while a low fade and disconnected top create bold contrast. A slightly disheveled, rugged texture, styled with wax or cream, keeps the look modern yet refined.

16. Clean Lived-In Haircut

Teenage boy with parted brushed-back lived-in haircut outdoors at golden hour wearing casual white and gray shirt

It gives a cool look with a timeless appeal. By letting the hair grow out and maintaining a parted, brushed-back style, it gives off a manly, powerful vibe. It’s all about having a relaxed yet refined look that works for both casual and more sophisticated styles.

17. Brushed Back Tapered Cut

Young boy with fine hair in brushed back tapered cut wearing gray shirt in romantic outdoor atmosphere

For those with fine hair, a progressive increase in length and weight creates a fuller, flattering finish. The blend of short edges and longer hair adds a sharp yet effortless balance.

18. Ridged Comb Over Style

Boy with ridged comb over hairstyle, hard part, skin fade, white tee, dark brown hair in romantic park atmosphere

Sharp edges, a defined hard part, and a skin fade eliminate hairlines. Styling cream and a wide tooth comb create a textured, cute disconnection on the top, combining classic and modern style with minimal maintenance.

19. Swept Back Taper on Straight Hair

Teen boy with swept back taper haircut on straight black hair wearing white shirt in romantic outdoor background

A taper style provides a sleek look with minimal upkeep, requiring less trimming than longer cuts. A small amount of styling cream on damp hair helps achieve a neat finish.

20. Burst Fade with a Wave Over

Realistic image of a man with burst fade and wave over haircut sitting in romantic café with black tee and confident expression

Combine a fade with a wave to add volume and texture to a medium undercut. Flip and sweep the hair, using a deep part and spray to keep the style in place.

21. Undercut with a Lengthy Top

Teenage boy with dark brown undercut and long top hairstyle in white shirt standing in a romantic urban park

This style features a short perimeter with a longer top, giving flexibility and a modern, neat look while avoiding the commitment of long hair. It’s both comfortable and easy to maintain.

22. Textured Disconnected Cut

Young man with a textured disconnected cut styled with gel, beige shirt, romantic background, and natural look

For those with groomed yet casual style, apply gel and style with fingers to add separation and definition, creating a sculpted look that feels fresh and tailored.

23. Tapered Spiked Haircut

Boy with tapered spiked haircut and choppy ends, styled with cream in romantic street setting at sunset

The style features choppy ends. By using a dryer and styling cream, you can sculpt the hair for a high, touchable finish, creating the right balance of structure and relaxation. It’s perfect for a more dynamic, personalized style.

24. Layered Comb Over Style

Teen boy with dark brown layered comb over hairstyle and ripple texture, sitting outdoors with romantic park background

A medium style with a laid-back look. Brushing the hair to the side adds sophisticated style, while the ripple effect provides depth. It’s a conservative, yet edgy style, perfect for both casual and more refined appearances.

25. High Fade with Swoopy Top

A real-looking photo of a stylish young man with a high fade haircut and a swoopy top, styled with a slicked-back, voluminous front. His hair is natural dark brown, thick and healthy, with a polished shine. He is wearing a fitted black leather jacket over a white t-shirt. He stands casually with one hand in his pocket, looking slightly to the side with a confident but relaxed expression—eyebrows slightly raised, a soft half-smile. The background features a warm, golden-hour city street with subtle romantic lighting, soft bokeh, and a light breeze brushing through his hair. The image must have realistic skin texture, natural lighting, and a perfectly natural-looking neck and jawline—no distortions or artificial blending. Ensure all facial features are sharp and symmetrical, matching real human proportions. The scene should feel modern, romantic, and editorial—like a real fashion photo shoot.

A high fade gives a sharp yet polished look, with the short fade at the sides providing a clean, businesslike touch and the slick back top adding a carefree, edgy vibe. It’s perfect for those wanting a modern, refined style.

26. Pompadour with Shaved Sides

Teenage boy with Pompadour and shaved sides hairstyle in white shirt posing confidently in romantic golden-hour background

The skin fades and barbered sides create a conservative style. Paired with a high fashion vibe, the cut feels avant garde, architectural, and cool, with a perfect balance of contrast.

27. Tapered Afro Hairstyle

Teen boy with tapered afro hairstyle featuring low fade natural curls and line-up in romantic outdoor setting

To style natural curls, trim the fade line low for a looser hairstyle and keep the top full. A line-up and sculpted edges add structure, creating a balance of geometric and organic shapes.

28. Undercut with a Twist Back Top

Boy with undercut twist back top hairstyle showing spiral rows on thick hair in romantic golden-hour background scene

For a fresh look, divide the top into rows and form soft spirals, helping to manage thick or frizzy hair. This technique offers a bespoke style while keeping the hair controlled and soft, with a clean yet playful finish.

29. Haircut with a Side-Spiked Fringe

Teenage boy with side-spiked fringe haircut, styled with wax and dryer, posing confidently in romantic outdoor background

Use wax to style the strands and a dryer to contour the fringe. The result is a flexible finish with strong hold that keeps your spikes in place throughout the day.

30. Mussed Waves with Shaved Sides

Realistic photo of man with dark brown mussed waves, shaved sides, beard, and undercut in romantic sunset setting

The style features waves on top and short sides, working with all hair textures, from fine to curly. The undercut creates a bold contrast, making the beard stand out and offering a hip look without feeling unruly.

31. Layered Cut on Thick Hair

Young man with dark layered thick hair and voluminous crown blowout styled for a bold bad boy look outdoors

Adding a cut to thick hair can reduce bulk and create movement, softening coarse strands. A blowout at the crown boosts volume, making the style stand out with a bad boy style.

32. Slick Back Hairstyle

Photorealistic boy with slicked back brown hair smiling in romantic park light wearing white shirt and jeans

This style provides a timeless, dynamic look with a touch of depth and texture. It’s perfect for achieving a boy next door appeal, allowing you to stand out effortlessly like a heartthrob. Whether refined or relaxed, it works with all hair types and keeps the look fresh.

33. Backcombed Style for Thin Hair

Man with backcombed thin hair featuring blonde to golden tips styled in a surfer vibe against a romantic beach backdrop

For those with lifeless hair, this technique creates a windblown look, while blonde highlights become even more noticeable when they grow out to golden tips. This style gives off a relaxed, surfer vibe, perfect for a casual yet stylish look.

34. Curled Tapered Haircut

Teen boy with curled tapered haircut and fade styled naturally in romantic outdoor golden hour setting

Combine textured curls with a perfect fade and edged hairlines for a dynamic look. Blow drying creates soft curls that fall flatteringly. Ask your barber for styling tips suited to your cut and hair type.

35. Brushed Back Wavy Hairstyle

Teen boy with dark brown brushed back wavy undercut hairstyle wearing a white T-shirt in a romantic outdoor setting

For a relaxed yet stylish look, leave an inch of hair on the sides of an undercut. You can blow it back or let it fall naturally for a less drastic, carefree vibe. This style gives a bold yet easy-going appearance without being too intense.

36. Wavy Low Taper Fade

Teen boy with a wavy low taper fade haircut, wearing white t-shirt, posing outdoors with sunset romantic background and natural expression

This style offers a fuss-free and stylish option that’s easy to manage. Simply brush and air dry for a quick, low-maintenance look. It also allows room to experiment with products without needing constant adjustments.

37. Sleek Clean Cut

"Young man with a sleek clean cut hairstyle, wearing navy blue shirt and denim jeans, in romantic setting."

The right cut can bring out your style, offering a sharp yet casual look. When paired with the right cut, it creates a flow that complements your natural look without overcomplicating things.

38. Brushed Over Style for Fine Hair

Teen boy with light brown brushed-over fine hair and undercut posing in romantic golden hour street scene

A brushed-over style with an undercut offers the perfect balance of sleekness and messiness. It’s ideal for a relaxed yet sharp look, maintaining an edgy yet sophisticated feel.

39. Asymmetrical Cut on Natural Waves

Teenage boy with natural wavy asymmetrical haircut wearing white tee in romantic sunset background

Keeping the front piece close to the cheek adds a stylish touch while embracing the natural flow of your hair. This style gives a trendy, edgy vibe that balances asymmetry with movement.

40. Gelled Pompadour Style

Teenage boy with gelled pompadour haircut and front strands falling over forehead in romantic outdoor setting

Adds height and definition by keeping the sides neat and allowing hair on top to stand out. Letting a few strands fall onto the face creates a relaxed look.

41. Haircut with Styled Back Elongated Layers

Real photo of boy with straight styled back elongated layers haircut sitting in park with romantic background

For a relaxed yet conservative style, try one that works well with straight hair. You can part it or pull it up for a more casual feel, offering endless possibilities without requiring much upkeep.

42. Short Ponytail with a Beard

Young man with short ponytail and full beard wearing black shirt in romantic outdoor background

A pulled-back updo and a full facial hair create a rugged, bold look. The mix of a pulled-back updo and the contrast of the hair offers a carefree yet fashionable vibe. It’s a practical way to stand out without much effort.

43. Swept Back Pompadour Cut

Teenage boy with a swept back pompadour cut wearing tattoos and piercings in a dreamy romantic outdoor setting

Try a retro cut with contrast. It’s ideal for showcasing personal style, especially with tattoos and piercings. It blends old school and new school for a modern appearance.

44. Haircut with a Sideburn Fade

Teen boy with black hair in a sideburn fade haircut sitting in park during sunset with confident expression

Fade adds a sharp contrast. Use a light paste to keep the style in place, maintaining a relaxed yet neat finish. The fade smooths the transition and completes the look.

45. Short Sides with Medium Top Cut

Realistic photo of a boy with short sides and medium top haircut styled with cream, in a romantic sunset street background

Use defining cream on wet strands. Allow hair to air dry for separation and definition, creating a controlled style. The short sides with a longer top enhance the natural texture.

46. Longer Back Haircut with Ear Tuck

Teen boy with longer back haircut and ear tuck in beige sweater, relaxed look with structured fine brown hair in romantic park setting

This hairstyle suits fine hair, offering a relaxed, dynamic look with natural movement and a sleek, structured feel while framing the face.

47. Styled Back Light Wispy Waves

“Light brown hair styled in back light wispy waves for boys, creating volume and movement with a romantic vibe.”

This hairstyle gives a relaxed, stylish look with wavy texture enhanced by mousses or creams. It adds volume, movement, and is perfect for curly hair, offering a sleek yet laid-back vibe.

48. Straight and Side-Parted Cut

Realistic image of a young man with straight and side-parted haircut, dressed in casual attire, showcasing a relaxed and trendy style.

A longer top with tight sides creates a balanced yet relaxed look. The side part adds structure while maintaining a spontaneous and cool feel. It’s perfect for casual and formal settings, offering a trendy, easy-to-style and maintain option.

49. Swept Back Gelled Hairstyle

Teenage boy with swept back gelled hairstyle and beige shirt in a romantic park setting during golden hour

Focus on creating a lift at the roots instead of making your hair flat, sleek, or wet. The style can be kept disheveled yet controlled, striking the right balance between structured and natural, perfect for any occasion.

50. Brushed Up Messy Top Haircut

Realistic photo of a boy with brushed up messy top haircut and tapered sides styled in a textured, casual finish

A short-to-medium haircut with top and tapered sides is perfect. It’s easy to create with pomade for a disheveled effect or more defined edges. Inspired by John Krasinski, this versatile option works well for expressing yourself.

Undercut hairstyle

What’s an Undercut Hairstyle?

This style keeps the top hair longer while cutting the back and sides short, creating volume and highlighting facial structure. It suits straight, wavy, and permed hair, with options for a subtle or bold look, especially for those with thicker hair, waves, or curls.

The Modern Undercut

"Realistic image of a man with a modern undercut hairstyle, wearing a black leather jacket, exuding confidence."

The undercut is a timeless and modern-day style that leads men’s trends, with A-list actors like Brad Pitt, Justin Timberlake, and Zak Efron rocking it in blockbuster films. Its bold, edgy look has become a popular and lasting choice in Hollywood.

Disconnected Undercut

The style features a contrast between longer hair on top and short sides, with an abrupt transition that creates an eye-catching look. It’s a unique, fashion-forward style that fits well with a hipster aesthetic.

Fade Haircuts—Low and High Fades

"Realistic photo of a man with a low fade haircut styled with volume and a confident look."

A fade can add a relaxed, stylish vibe with a low fade that works well with long or medium hair, adding volume. The high fade provides a sharper look, with a fade line higher on the sides, and pairs perfectly with a pompadour, quiff, or comb-over. These fades provide different levels of sleekness, allowing for versatile looks depending on your preference.

Undercut with Beard

Man with undercut hairstyle and well-groomed beard in romantic setting, wearing navy blue shirt.

Consider how your facial hair affects your look. Whether clean or full, ensure your hair and facial hair complement each other for a balanced, polished appearance.

Will an Undercut Suit You?

To choose the right style, focus on your facial structure, head shape, and beard preferences. Compare your features with models who resemble you, and ask your hairstylist for an honest opinion and any necessary adjustments. This ensures the style suits your natural traits and works well for both social and business settings.

Men’s Undercut Hairstyles by Length of Top Hair

When deciding, think about how much you want to keep. The size of your hair plays a big role in determining the result. Whether you prefer long or short, there are trendy options to suit. The key is balancing for a well-groomed look.

Short Undercut Hairstyles

"Man with short undercut hairstyle in casual outfit, showcasing a bold yet functional look in a romantic setting"

Shorter cuts offer minimal maintenance and allow for creativity. They can range from suave to loud, making them perfect for those seeking a bold yet functional look.

Medium Undercut Hairstyles

"Real-life image of a young man with medium undercut hairstyle, confident expression, and romantic background."

Emphasizing your hair’s natural properties with a striking look, it offers a perfect balance of length, making it an easy choice. Popular, it’s ideal for those looking to make a statement, and with a little maintenance, it’s easy to achieve.

Long Undercut Hairstyles

"Long undercut hairstyle for men with short sides, styled for a bold, individualistic look in a romantic sunset setting."

The striking look created with short sides and long hair on top is popular among men in creative fields, offering a way to express their freewheeling spirits. The unique style has gained attention for its bold, individualistic flair.

Undercut Hairstyles Variations

Wavy Hair Undercut

"Young man with wavy undercut hairstyle in leather jacket, exuding confidence and style with a romantic background."

Embrace your untamed lines and join the trend many male models and creative men are wearing. Choose a detached undercut that fits your consistency and use wax to maintain the shape and make a strong mark.

Curly Hair Undercut

If you have curls, leaving the top longer with a shorter cut can help emphasize them. It’s important to know your hair to ensure your curls look full and robust, giving the look a natural finish.

Undercut with Fringe

Considering a cut works well for different hair types. The cut should ideally be long enough to cover your forehead and is perfect for people with larger or longer, as it helps to shorten face length.

Undercut Quiff

A sharp cut or a gradual can showcase the difference in length, giving you a suave vibe. A taper is another option for a more understated look, allowing you to adjust to your preferences.

Undercut Mohawk

Loving the boldness but concerned about perception? It offers a daring look while keeping it acceptable in various environments. With short sides, you can still achieve a confident vibe without feeling over-the-top.

Side Part Undercut

Undercut is a timeless option that can easily transform your appearance. Originating in the Victorian era and making a comeback, it’s simple yet dramatic. Changing your part can breathe new life into your classic while staying on-trend.

Hard Part Undercut

A visible line separates the top from the rest, creating a disconnected and elevated style. It’s a classier version of a side-part, offering flexibility to change with a comb over or slick back. Perfect for various situations, it’s a popular choice for guys.

Side Swept Undercut

It works well for wavy hair, especially when it’s longer. It offers a balance of wild and dapper, and a simple photo helps your stylist understand the look you want. It’s perfect for a bold yet manageable refresh.

Long Fringe Side Swept Undercut

The short sides with a longer top create a striking style. The extra length on top adds personality, while the trimmed sides provide contrast. This bold style is perfect for those who want to make a confident statement.

Pompadour Undercut

When you pair a highly styled top with a close shave on the sides, you get a striking contrast that’s sure to turn heads and announce your arrival with confidence. It’s a fun and sharp look that makes you stand out.

Hard Part Pompadour Undercut

A disconnected undercut with a voluminous top requires precision and skill, so it’s important to show your barber a picture and discuss your goals. The result is a look that sets you apart.

Slicked-Back Undercut

This style combines short sides with a long top, styled back for a sharp, high-contrast look. It suits professionals and casual settings alike, and should be customized by your barber to fit your hair length and type.

Undercut with Comb-Over or Brushed Back

"Young man with undercut comb-over hairstyle in casual jacket, exuding confident style."

For a well-groomed style, try a look that works with medium length hair. This versatile style can be tailored to your taste and holds well with pomade or styling wax, especially if you want to keep the top in place. The key is adjusting it to suit your preferences for a confident look.

Origins of Undercut Hairstyles

"Realistic photo of a man with an undercut hairstyle in a 1920s vintage suit, exuding confidence."

The hairstyle became popular in the 1920s, evolving throughout the 20th century with a blend of practicality. It was favored by businessmen, jazz performers, and soldiers. Later, various styles were embraced by both youth culture and established men, offering a timeless freshness and aliveness.

The Keys to Success with an Undercut Hairstyle

For the best undercut, focus on precision, clear communication with your barber, and regular trims. Choose a cut that suits your face shape, and maintain it with proper grooming tools.

1. Know What You Want

Before your next appointment, ensure you have a clear idea of the style you want. Describe it to your hairstylist and bring a photo to show them. This will help avoid confusion and ensure you’re both on the same page.

2. Be Open to Making Adjustments

When discussing your look with your stylist, share your preferences but trust their expertise to suggest refinements. Small alterations based on their feedback can result in a better final style that suits you perfectly.

3. Watch, Learn and Ask

Observe your stylist during the cut and note the products and techniques used. Be sure to ask for advice on maintaining the look and choosing the right products for your hair type.

4. Maintenance

Regular trims at the barbershop are key to keeping your undercut sharp. While you can use clippers for touch-ups at home, the timing for trims depends on how quickly your hair grows and the style you have.