You probably hit that point where your hair feels too long for a buzz cut but too short for a ponytail. Welcome to the medium-length sweet spot, my friend. Most guys panic during this “awkward phase,” but honestly, this length offers the most versatility you will ever have.
I remember my first attempt at growing out my hair; I looked like a stray poodle for three months because I didn’t have a plan. You don’t have to suffer that same fate. If you play your cards right, you can look like a movie star while everyone else looks like they missed their barber appointment.
Ready to stop fighting your hair and start styling it? Let’s look at 15 medium-length hairstyles that actually work without making you look like a 90s boy band reject (unless that’s what you want).
1. Textured Medium Crop
The Textured Medium Crop stands as the ultimate “cool guy” haircut for anyone who wants movement without the mess. It involves keeping the sides slightly shorter while leaving the top long enough to play with. This style relies heavily on point-cutting to create those jagged, textured ends.
Do you hate spending twenty minutes in front of the mirror? This look is your best friend because it thrives on imperfection. I find that a matte clay works best here to keep the hair looking natural rather than greasy.
- Best for: Thick or wavy hair types.
- Maintenance level: Low to medium.
- Key tool: A high-quality sea salt spray.
Texture makes all the difference when you want to avoid that flat, helmet-head look. You just rub a bit of product between your palms, mess it through your hair, and you look like you actually tried today.
2. Classic Tapered Medium Cut
If you work in an office or just want to look like a functioning member of society, the Classic Tapered Medium Cut is your winner. This style keeps the hair longer on top but features a gradual taper down the sides and back. It provides a clean silhouette while still giving you enough length to style.
Ever notice how some haircuts look great for exactly one week? The taper avoids that problem because it grows out incredibly well. I always tell my barber to keep the neck line “tapered” rather than “blocked” to keep it looking fresh longer.
- Best for: Straight or slightly wavy hair.
- Vibe: Professional yet approachable.
- Pro tip: Use a light cream for a soft finish.
Clean edges define the look, so don’t skip those neck trims between full haircuts. It keeps the “medium” length from looking like a “messy” length.
3. Layered Medium Flow
The Layered Medium Flow is basically the “I just got back from the beach” look for people who haven’t seen the ocean in years. This style utilizes long layers to remove weight and encourage natural movement. If your hair feels heavy or “poofy,” layers will save your life.
I personally love this look because it requires almost zero “styling” in the traditional sense. You just need to keep your hair healthy so the flow actually flows instead of frizzing out. IMO, this is the most relaxed look on this entire list. 🙂
- Why it works: It frames the face and softens harsh jawlines.
- Required product: Leave-in conditioner to prevent frizz.
- Face shape: Works wonders for heart or diamond shapes.
Gravity does the work here, so don’t fight it with heavy waxes or gels. Let the layers sit where they want to go naturally.
4. Medium Length Quiff
Think of the Medium Length Quiff as the more sophisticated cousin of the pompadour. You keep significant length at the front and brush it upward and slightly back. It creates incredible volume and makes you look taller, which is a nice little bonus.
Do you struggle with flat hair that lacks personality? The quiff fixes that by providing a clear focal point at the front of your head. I usually use a blow dryer to train the roots to stand up before I even touch any product.
- Essential step: Blow-dry hair upward while damp.
- Hold type: Firm hold pomade or hairspray.
- Sarcasm alert: Yes, people will ask why your hair is so tall. Just tell them it’s full of secrets.
Height is the goal, so focus your styling efforts on the front two inches of your hairline. If the front looks good, the rest usually follows suit.
5. Messy Medium Waves
If you have naturally curly or wavy hair, please stop trying to slick it down. The Messy Medium Waves style celebrates your natural texture by letting it do its own thing. You keep the hair at a uniform medium length and use a curl-enhancing cream to define the shape.
I’ve seen too many guys fight their curls with heavy gel until they look like a LEGO figurine. Why do that to yourself? Embrace the chaos and let those waves bounce around a bit.
- Styling tip: Scrunch your hair while it’s wet to encourage the wave.
- Avoid: Using a fine-tooth comb (it’ll just make you look like a dandelion).
- Best product: A moisturizing curl cream.
Control the frizz, not the hair, and you will find that people pay a lot of money to get the texture you were born with.
6. Medium Side Part Style
The Medium Side Part is the “old reliable” of the hair world. It’s timeless, it’s clean, and it works for almost every occasion from a wedding to a grocery store run. By keeping the hair at medium length, you get a gentle sweep rather than a harsh, glued-down line.
I think every man should master the side part at some point in his life. It gives you an instant boost of “I have my life together” energy, even if you’re currently eating cereal for dinner. FYI, finding your natural part makes styling this a billion times easier.
- How to find it: Comb your hair forward and see where it naturally splits.
- Finish: High shine for formal, matte for casual.
- Maintenance: Easy.
Precision matters here, so use a comb to get that line straight. Once you set the part, you can style the rest with your fingers for a more modern vibe.
7. Medium Length Brush Back
The Medium Length Brush Back is for the guy who wants to look like he just stepped off a motorcycle. You comb all the hair back away from the face, but you don’t slick it down flat. You want to maintain volume and airiness so it looks effortless.
Ever wondered why some guys look so effortlessly cool with their hair pushed back? They probably aren’t using heavy grease. I prefer a medium-hold styling foam because it keeps the hair in place without making it crunchy.
- Key feature: No visible part.
- Vibe: Rugged and masculine.
- Hair type: Best for straight or slightly wavy hair.
Keep the sides tucked, and the top will do all the heavy lifting. This look keeps your hair out of your eyes while showing off your facial features.
8. Medium Modern Shag
Don’t let the name “shag” scare you off; the Medium Modern Shag is a far cry from the 1970s disaster. Today’s version features heavy texturizing and choppy layers that create a rock-and-roll aesthetic. It’s perfect for the guy who wants to look a little edgy and doesn’t mind a bit of hair in his eyes.
I find this style works best when you haven’t washed your hair for a day or two. The natural oils help the “shaggy” pieces clump together in a way that looks intentional rather than messy.
- Who it’s for: Guys with a bit of an “alt” or creative style.
- Styling tool: Your fingers (forget the comb).
- The “Secret”: Using a dry shampoo for volume.
Embrace the texture and don’t try to make it look perfect. The more “undone” it looks, the better the shag actually works.
9. Medium Length Slick Flow
The Medium Length Slick Flow sits somewhere between a slick back and a long-hair flow. You use a high-shine pomade to pull the hair back, but you allow the ends to flip out or curl naturally at the back. It’s a very “refined outdoorsman” look.
I think this style looks incredible with a well-groomed beard. It balances the “pretty boy” hair with some rugged facial hair. If you have thick hair that refuses to stay down, the “slick” part of this style will finally give you some control.
- Best combo: Medium hair + 3-day stubble.
- Product: Water-based pomade (easier to wash out).
- Note: Watch out for “helmet head” by using a wide-tooth comb.
Control the roots but let the ends go, and you’ll achieve that perfect balance of groomed and natural.
10. Medium Haircut with Low Fade
If you love the medium length but hate how it looks around your ears, the Medium Haircut with Low Fade is your solution. You keep 4-6 inches of hair on top but ask your barber for a sharp low fade on the sides. This creates a high-contrast look that looks incredibly modern.
The fade acts like a frame for the “main event” on top of your head. It keeps you looking groomed even if the top is a bit wild. I usually get my fade touched up every two weeks to keep it looking crisp.
- Benefit: Keeps you cool in the summer.
- Contrast: High contrast between the skin and the long hair.
- Maintenance: Requires regular barber visits.
The fade provides the structure, allowing you to be as creative as you want with the length on top.
11. Medium Length Curtains
Yes, the 90s are back, and Medium Length Curtains are leading the charge. This style involves parting the hair down the middle (or slightly off-center) and letting it fall on either side of the face. It works best when the hair hits around the cheekbones or ears.
I’ll admit, I was skeptical about this coming back, but it actually looks great on guys with strong jawlines. Just make sure you aren’t doing the “greasy” version from middle school. Keep it clean, keep it voluminous, and you’re golden.
- Modern twist: Keep the sides slightly tapered so it doesn’t look like a mushroom.
- Styling tip: Use a round brush while blow-drying to get that “flip.”
- Vibe: Artistic and trendy.
Balance is key—ensure both sides have equal volume so you don’t look lopsided. 🙂
12. Medium Voluminous Top
The Medium Voluminous Top focuses all the energy on height and fullness. This isn’t just a quiff; it’s a full-on celebration of hair density. You want the hair to look thick and healthy from the hairline all the way to the crown.
If you have fine hair, don’t worry—you can still pull this off with the right products. I swear by volumizing powder; you just sprinkle it at the roots, and suddenly you have twice as much hair.
- Main goal: Density and lift.
- Required product: Pre-style with a thickening spray.
- Avoid: Heavy waxes that weigh the hair down.
Lift from the roots using your blow dryer and a vent brush to maximize the space between your strands.
13. Medium Length Undercut Blend
The Medium Length Undercut Blend takes the classic undercut and makes it a bit more “grown-up.” Instead of a harsh shaved line, the barber blends the transition from the short sides to the long top. This gives you the sleekness of an undercut without the “angry teenager” vibes.
I love how versatile this is. You can slick it back for a formal event or let it hang loose for a casual day out. It’s like having two haircuts in one.
- Versatility: High.
- Styling time: 5-10 minutes.
- Pro tip: Tell your barber to “seamlessly blend” the parietal ridge.
The blend softens the look, making it much more wearable for the average guy who isn’t a runway model.
14. Medium Natural Look Cut
Sometimes, the best style is the one that doesn’t look like a “style” at all. The Medium Natural Look Cut follows the natural growth pattern of your hair. The barber simply cleans up the edges and removes bulk where necessary, leaving you with a balanced, easy-to-manage shape.
This is the ultimate low-maintenance look. If you value your sleep more than your hair routine, this is the one for you. I find that a tiny bit of grooming cream is all you need to keep it from looking flyaway.
- Philosophy: Less is more.
- Hair type: Works for everyone.
- Daily effort: 30 seconds.
Healthy hair is the focus, so invest in a good shampoo and conditioner rather than expensive styling products.
15. Medium Length Casual Style
Finally, we have the Medium Length Casual Style. This is the look you see on guys who look great without ever appearing like they tried. It’s a bit messy, a bit structured, and totally flexible. You can push it to the side, brush it back, or let it fall forward.
Think of this as your “baseline” medium haircut. It’s the perfect starting point if you’re just beginning your medium-length journey. IMO, it’s the safest bet for any guy transitioning from short hair.
- The Look: Relaxed and effortless.
- Product: A light-hold clay or paste.
- Final thought: It’s the “jeans and a white t-shirt” of hairstyles.
Flexibility defines this cut, so don’t be afraid to change how you wear it depending on your mood that day.
Why Medium Hair Wins Every Time
Are you still on the fence about keeping the length? Let me try to convince you. Short hair is easy, sure, but it’s also a bit… boring? Long hair is majestic, but it’s also a massive pain to wash and dry.
Medium hair is the Goldilocks zone. You have enough hair to hide a weirdly shaped head (we all have them), but not so much hair that you’re clogging the shower drain every morning. Plus, you can change your look entirely just by changing your product.
- Want to look professional? Slick it back.
- Want to look like a rebel? Mess it up with some salt spray.
- Date night? Add a bit of shine and a clean part.
Does short hair give you that many options? Nope. It just sits there.
Choosing the Right Product for Your Medium Look
You can have the best haircut in the world, but if you use the wrong “goop,” you’re going to look like a grease fire. Medium-length hair requires a delicate touch.
If you use a heavy, high-hold wax on four inches of hair, you’re going to end up with a solid block of granite on your head. Here is a quick cheat sheet for what you should actually be buying:
- Sea Salt Spray: This is the MVP for medium hair. It adds “grit” and texture without making the hair feel heavy. Use it on damp hair before you blow-dry.
- Matte Clay: Perfect for those “messy” and “textured” looks. It provides a strong hold but leaves a natural, non-shiny finish.
- Grooming Cream: If you have dry or frizzy hair, this is your savior. It adds moisture and a light hold for those “natural” styles.
- Volumizing Powder: If your hair is flat and sad, this powder will give it an instant “poof” at the roots.
Don’t overdo it. Start with a pea-sized amount. You can always add more, but you can’t exactly “un-apply” pomade without jumping back in the shower.
The “Awkward Phase” Survival Guide
I won’t lie to you; there will be a month where your hair looks like a mushroom. It’s a rite of passage. But you can survive it if you follow a few simple rules.
First, keep the neck clean. As long as the back of your neck isn’t hairy, people will assume your haircut is intentional. If you let the neck hair meet your back hair, you just look like you’ve given up on life.
Second, use hats strategically. On days when your hair refuses to cooperate, a baseball cap or a beanie is a perfectly acceptable solution. Just don’t wear a hat 24/7, or your hair will never learn how to sit correctly.
Third, visit your barber anyway. Tell them, “I’m growing it out, but please clean up the edges and remove some weight.” A good barber knows how to shape hair while it’s growing so it never looks like a total disaster.
Factoring in Your Face Shape
Not every medium look works for every face. I learned this the hard way when I tried to pull off a middle part with a very round face. I looked like a giant thumb.
- Round Faces: You need height. Go for the Quiff or the Voluminous Top. Avoid anything that adds width to the sides.
- Square Faces: You can handle almost anything. Slick Backs and Side Parts highlight your jawline perfectly.
- Oval Faces: You are the lucky ones. Every single one of these 15 looks will work for you. Try the Curtains or the Shag just because you can.
- Long Faces: Avoid too much height on top. Go for the Flow or the Waves to add some width to the sides of your head.
Know your angles, and you’ll choose a cut that highlights your best features instead of hiding them.
The Active Voice Lifestyle
You should treat your hair like a project you manage, not something that just happens to you. You style it. You wash it. You shape it.
When you take an active role in your grooming, you feel more confident. There is a psychological boost that comes from knowing your hair looks exactly how you intended. People notice that confidence.
So, which one of these 15 looks are you going to try? Maybe you’ll start with the Classic Taper and work your way up to the Modern Shag. Whatever you choose, just remember that hair grows back. If you hate it, you can change it in a month. :/
Conclusion: Finding Your Signature Style
We’ve covered a lot of ground here, from the structured Side Part to the chaotic Messy Waves. The beauty of medium-length hair lies in its ability to adapt to your life. You aren’t stuck with one look; you’re given a canvas that you can change every single morning.
Maintenance and product choice will determine whether your hair looks like a masterpiece or a mistake. Don’t be afraid to experiment with different clays, sprays, and creams until you find the perfect “cocktail” for your specific hair type.
Remember, the best hairstyle is the one that makes you feel like the best version of yourself. Whether you’re going for “CEO of a tech company” or “Lead singer of an indie band,” these 15 looks provide the foundation you need.
Go see your barber, show them a picture of one of these styles, and start your medium-length journey today. You might just find that the “awkward phase” was actually the beginning of your best look yet.
Now, go grab some sea salt spray and show the world what you’ve got. Your hair will thank you later. 🙂
