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Top 20 Looks of Medium Long Hairstyles for Teenage Guys

Medium-long hair is a win for teens who want to keep things cool and versatile. You can go messy, sleek, or in between—there are no rules, just pure style. Check out these 20+ Medium Long Hairstyles looks that are easy to pull off and perfect for school, hangouts, or just showing off your vibe.

Messy Textured Layers

This style screams, “I didn’t try too hard,” but it still looks fantastic. Layers give your hair a dynamic feel. Just rake your fingers through it with matte paste, and you’re ready. It works with straight, wavy, or even slightly curly hair, making it a no-brainer for daily wear.

Messy Textured Layers
Image source: Pinterest

Classic Shag Cut

Throw it back to the 70s with a shaggy, rock star-inspired cut. Choppy layers and uneven ends keep it carefree—no fancy hair styling is needed. Spritz some sea salt spray and let your hair air-dry for that perfect bedhead look. This cut is ideal for guys who want to keep it edgy without the fuss.

Classic Shag Cut
Image Source: Pinterest

Man Bun (Topknot)

Do you have thick hair? Tie it up in a loose bun at the crown and let a few pieces frame your face. It’s one of the practical medium-long hairstyles for sports or hot days, and pairing it with faded sides adds a modern edge. Bonus: It takes two minutes to style and looks effortlessly cool.

Man Bun
Image Source: Pinterest

Side-Swept Undercut

Sharp and bold, this look mixes short sides with a longer top swept to one side. A tiny bit of pomade keeps the style in place without looking too stiff. It’s excellent for looking put-together but still relaxed—think school photos or weekend hangouts.

Side-Swept Undercut
Image Source: Pinterest

Beachy Surfer Waves

Bring the beach to your everyday look with tousled, windswept waves. Even if your hair’s straight, scrunch damp hair with sea salt spray and let it dry naturally. If you are looking for Medium Long Hairstyles then this laid-back style pairs with hoodies, tees, or anything casual—perfect for that “chill surfer dude” energy.

Beachy Surfer Waves
Image Source: Pinterest

Layered Pompadour

Go retro with a pompadour that’s all about volume on top and clean sides. Brush the front upward for height and lock it in with a strong-hold gel. It’s a standout style for parties or events, giving off major confidence without trying too hard.

Layered Pompadour
Image Source: Pinterest

Curtain Bangs

Channel 90s vibe with a middle part and soft, face-framing layers. Blow-dry your bangs forward for a subtle swoop that adds a touch of charm. This style works for straight or wavy hair and keeps things fresh and youthful.

Curtain Bangs
Image Source: Pinterest

Messy Fringe

Let your front layers fall loosely over your forehead for a carefree, edgy vibe. A quick finger comb is all you need to keep it looking intentional. This style is perfect for guys who want a low-maintenance style that still makes a statement.

Messy Fringe
Image Source: Pinterest

Half-Up, Half-Down

Tie the top half into a mini bun or ponytail and let the rest free. It’s playful and practical—great for concerts, skate sessions, or just mixing things up. Tease the crown a little for extra volume and a touch of rebellion.

Half-Up, Half-Down
Image Source: Pinterest

Slicked-Back Style

Need to look sharp? Comb your hair back with a light gel for a polished finish. Keep the gel minimal to avoid that stiff, helmet-head look. It’s sleek enough for formal stuff but still feels laid-back if you hit the mall afterward.

Slicked-Back Style
Image Source: Pinterest

Spiky Ends

Add a dash of attitude with subtle spikes at the crown. Use matte clay to lift sections of hair and keep the rest messy for balance. Straight or fine hair? This style gives you an instant edge without going over the top.

Spiky Ends

Braided Accents

Add a small braid (like a loose side cornrow) to your medium-length hair for a unique twist. Keep it relaxed and undone—it’s a subtle way to stand out in class or at a friend’s BBQ.

Braided Accents
Image Source: Pinterest

Wavy Mullet

Yes, mullets are back—but cooler. Keep the sides short, let the back grow out, and add soft waves on top. It’s bold, TikTok-approved, and perfect for guys who love mixing retro and modern vibes.

Wavy Mullet
Image Source: Pinterest

Textured Quiff

Lift the front of your hair into a voluminous quiff for a confident, head-turning look. Blow-dry while brushing upward, then finish with a light spray. Straight hair? This style adds drama without feeling too extra.

Textured Quiff
Image Source: Pinterest

Messy Curls

Got natural curls? Let ’em loose! Scrunch in some curl cream to fight frizz and boost definition. It’s a carefree style that works for school, dates, or just owning your texture with pride.

Messy Curls
Image Source: Pinterest

Faux Hawk

Trim the sides short and spike up the middle section for a subtle Mohawk vibe. A bit of wax keeps it edgy but not too wild. Pair it with joggers and sneakers for Medium Long Hairstyles.

Faux Hawk
Image Source: Pinterest

Long Side Part

Comb your hair to one side with a deep part for a classic, clean look. This style works with straight or wavy hair and can be kept neat or slightly messy. It’s versatile enough for presentations or weekend coffee runs.

Long Side Part
Image Source: Pinterest

Grunge Shag

Go full 90s grunge with messy layers, choppy ends, and a don’t-care attitude. Dry shampoo adds grit and volume—perfect for guys who want that “just left a concert” look every day.

Grunge Shag
Image Source: Pinterest

Twisted Buns

Try two small buns on top for a fun, quirky vibe. Curly or thick hair? This style shines at festivals or theme parties. Secure them with bobby pins and own the playful energy.

Twisted Buns
Image Source: Pinterest

Layered Wolf Cut

This viral style mixes shaggy layers with a hint of mullet for a wild, textured look. Spritz on texturizing spray and let your hair air-dry to embrace the messy, undone aesthetic.

Layered Wolf Cut
Image Source: Pinterest

Final Thoughts

Medium-long hair is your way to looking sharp without trying too hard. Messy layers, surfer waves, or even a bold undercut—these styles are all about mixing fun with personality. Find what feels like you, mess around with different vibes, and keep it low-key. Do share with us which style you liked the most.