You're stuck. Your hair is too long to be a crew cut but not quite long enough to reach your shoulders, and honestly, you probably feel like a mushroom most days. It’s that weird, shaggy, "I forgot to visit the barber for three months" look. But here is the thing: medium length men long hair is currently the most versatile sweet spot in men’s grooming, even if it feels like a nightmare to style.
Most guys give up here. They get frustrated with the way their ears poke out or how the back flips up like a 1970s TV host. They go back to the fade. They lose. If you can actually manage this length, you unlock a range of styles that short hair simply can't touch. We’re talking about the "bro flow," the relaxed side part, and that effortless textured look that makes it seem like you just rolled out of bed looking like a movie star. It takes work to look that lazy.
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The awkward phase is a myth you can fix
Let’s be real. The "awkward phase" is just a lack of a plan. When people talk about medium length men long hair, they usually picture someone who just stopped cutting their hair entirely. That’s a mistake. If you don't shape it, gravity takes over in all the wrong places. Your hair grows at different rates; the hair on your neck (the nape) often feels like it's racing to your shoulders while the top stays stubborn.
You need a "transition cut." This is where you tell a stylist—not a cheap barbershop that only knows how to use a #2 guard—that you are growing it out. They need to take the weight out. They’ll use thinning shears or point-cutting to make sure the hair collapses into itself rather than poofing out like a dandelion. It sounds counterintuitive to cut hair when you want it long, but removing bulk from the sides is what keeps you from looking like a Lego man.
I’ve seen guys try to power through without a single trim for six months. It never works. By month four, the proportions are so off that they look bottom-heavy. A quick clean-up around the ears and a slight taper at the neck keeps the silhouette masculine. It’s about maintaining a shape that follows the bone structure of your skull rather than fighting it.
Products: Stop using whatever is in the shower
If you are still using 3-in-1 shampoo, stop. Seriously. Short hair can survive that kind of abuse because it’s "new" hair—it hasn't been exposed to the elements for long. But once you move into the territory of medium length men long hair, the ends of your hair might be six months to a year old. They’re tired. They’re dry. They’re thirsty.
You need moisture.
- Sea Salt Spray: This is the holy grail for medium length. It provides grit. Without it, medium hair often lies flat and looks greasy. A few spritzes on damp hair gives you that "just came from the beach" volume.
- Matte Paste or Clay: Avoid shiny gels. Shiny medium hair looks like you’re trying to be a 1920s mobster. You want a matte finish that allows for movement. You should be able to run your hands through your hair without it feeling like a crunchy shell.
- Leave-in Conditioner: Use this once or twice a week. It prevents the frizz that happens when medium hair air-dries in humidity.
Matty Conrad, a world-renowned barber and founder of Victory Barber & Brand, often emphasizes that "the longer the hair, the more it needs a foundation." He’s right. If you just let it sit there, it looks limp. You need a product that adds "memory" to the hair so it stays back from your face without needing a headband.
Styling the "Flow" without looking like a 90s boy band
The "Flow" is the quintessential look for this length. It’s what you see on NHL players and actors like Timothée Chalamet or Dev Patel. It’s all about direction. Most guys make the mistake of combing everything straight back. Unless you have the jawline of a Greek god, this usually looks a bit harsh.
Instead, try the diagonal back sweep. Use a blow dryer. I know, most guys hate blow dryers. They think it's too much effort. But three minutes with a blow dryer on a medium heat setting will save you twenty minutes of frustration later. Use your fingers to pull the hair up and back. This creates "lift" at the roots. If the roots stay flat, the hair falls into your eyes. If the roots have lift, the hair arches over your forehead and stays put.
Another tip? Don't over-wash. Your scalp produces natural oils (sebum) that are actually great for medium length men long hair. When you wash every single day, you strip those oils away, and your hair reacts by getting frizzy or overproducing oil to compensate. Aim for two or three times a week. On the off days, just rinse with water or use a dry shampoo if you’re feeling oily.
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Choosing a style based on your face shape
Hair isn't one-size-fits-all. What looks good on a guy with a square jaw might look terrible on someone with a round face.
If you have a rounder face, you want height. Keep the sides a bit tighter and let the top have all the volume. This elongates your head. If you have a very long or oval face, avoid too much height on top. Instead, let the sides grow out a bit more. This adds width and balances everything out. It’s basic geometry, really.
For guys with a receding hairline, medium length can actually be a savior—or a curse. If you grow it long and try to "comb over" the thin spots, everyone can tell. However, if you keep it messy and textured, the layers can mask thinning areas by adding visual depth. It’s all about creating shadows and movement.
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Real-world maintenance
Don't forget the neck. Even with medium length men long hair, a hairy neck looks sloppy. You can keep the length on top but have your barber do a "tapered nape." This keeps the edges looking sharp while the rest of the hair flows over it. It’s the difference between looking like a professional who likes long hair and looking like someone who just gave up on hygiene.
Also, watch the tuck. Tucking your hair behind your ears is a habit most guys develop at this length. It’s fine, but it can train your hair to flare out at the bottom. If you want a cleaner look, use a bit of medium-hold cream to keep the hair just in front of the ears or let it fall naturally.
The psychology of the cut
There is a certain confidence that comes with this length. It’s not as "safe" as a buzz cut. It requires you to actually care about your appearance, which some guys find daunting. But there’s a reason why the "quiet luxury" aesthetic often features this specific hair length. It suggests you have the time and the resources to maintain it. It’s relaxed but intentional.
Practical Next Steps
- Stop the 3-in-1 habit. Buy a dedicated conditioner and use it every time you shower, even if you don't use shampoo. Focus on the ends of the hair, not the scalp.
- Find a stylist, not a clipper-only barber. Search for someone who specializes in "scissor cuts" or "long hair for men." Look at their Instagram. If all they post are skin fades, they aren't the person for this job.
- Invest in a Sea Salt Spray. Apply it to towel-dried hair, scrunch it in with your hands, and let it air dry or use a blow dryer on low. This is the simplest way to get instant texture.
- Schedule "maintenance trims" every 6-8 weeks. Tell them you want to keep the length but "remove weight and clean up the perimeter." This prevents the mushroom shape.
- Be patient. Hair grows about half an inch per month. To get a true medium length that has "flow," you're looking at a 6 to 9-month commitment from a short starting point. Don't cut it off during month four just because you had one bad hair day.