Let’s be real for a second. Most men have spent their lives being told that "looking professional" means a tight fade and a side part. It’s a lie. Honestly, the rise of the "relaxed executive" and the general death of the 9-to-5 office grind has blown the doors wide open for something better. We are talking about long messy hairstyles guys can actually pull off without looking like they haven't showered since the Obama administration. It’s about intentional chaos.
You’ve seen it on Timothée Chalamet. You’ve seen it on Dev Patel. It looks effortless, right? Wrong. That "I just rolled out of bed and happen to be a Greek god" look takes a specific strategy, the right products, and a barber who understands that thinning shears are sometimes the enemy. If you just let your hair grow without a plan, you don't get a hairstyle; you get a curtain.
The secret is texture. Without it, long hair just hangs there. It’s flat. It’s boring. But when you dial in the layers and the volume, you get that rugged, lived-in aesthetic that works at a wedding just as well as it does at a dive bar.
Why the Shag is Making a Massive Comeback
The modern shag is basically the king of long messy hairstyles guys are asking for right now. Think 1970s rockstar but cleaned up around the edges. It’s all about the layers. If your hair is all one length, the weight pulls everything down, making your face look longer and—honestly—a bit tired. By adding internal layers, you’re removing weight from the middle of the hair shaft, which allows the ends to flick out and move.
It's a vibe.
Stylist Sally Hershberger, who basically invented the modern shag for women, has often noted that the key to great hair is "movement and mess." For guys, this translates to a cut that follows the natural growth pattern. If you have a cowlick, don't fight it. Lean into it. A great shag uses your hair's natural tendency to flip or curl to its advantage.
You need a sea salt spray. Seriously. If you aren't using one, you’re missing out on the easiest way to get that "beach grit" texture. Just spray it on damp hair, scrunch it with your hands, and let it air dry. Don't touch it. The more you touch it while it dries, the more frizz you create.
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The Surprising Truth About the "Man Bun" Transition
Look, the man bun got a bad rap because people did it poorly. But as a transitional phase for long messy hairstyles guys are growing out, it’s a lifesaver. When you’re at that awkward length—too long to style with pomade, too short to tuck behind your ears—you need a "hiding" strategy.
But here is the thing: don't make it tight.
Tight buns cause traction alopecia. That’s a fancy way of saying you’re pulling your hairline back until it stays there permanently. Not good. Instead, go for a loose, messy loop at the crown. Let the "flyaways" happen. Those little strands of hair falling around your face are what make it look like a style rather than a desperate attempt to contain a mop.
If you're in this middle stage, you have to embrace the headband. Not the plastic ones from the drugstore. Get a soft, fabric gaiter or a thin metal band that blends with your hair color. It keeps the hair out of your eyes while you’re working but maintains that messy, textured volume in the back.
Maintenance Is the Part Nobody Tells You About
You can't just stop getting haircuts. That’s the biggest mistake guys make when going for a long, messy look. You actually need to see your barber more often, or at least more strategically. You’re going in for "dustings."
A dusting is where the stylist just clips the very ends to prevent split ends from traveling up the hair shaft. If you don't do this, your hair will eventually look thin and fried at the bottom. It stops looking like a "style" and starts looking like a cry for help.
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- Frequency: Every 8 to 12 weeks.
- The Goal: Maintain the shape, remove the bulk, and save the length.
- The Tool: Professional shears or a razor. Never let a barber use a guard or clippers on the bulk of a long messy style. It creates blunt lines that ruin the "messy" effect.
Texture paste is your best friend here. Unlike gel, which gets crunchy and weird, or pomade, which is too greasy for long hair, a matte paste gives you hold without the shine. Take a pea-sized amount, rub it between your palms until it’s warm, and then rake your fingers through the mid-lengths to the ends. Avoid the roots unless you want to look like you haven't washed your hair in a week.
Dealing with Different Hair Types
Not all messy looks are created equal. If you have stick-straight hair, you’re going to have a harder time than the guy with natural waves. Straight hair tends to look limp when it’s long. To fix this, you need a volumizing powder. You puff it onto the roots, and it creates "grip." It’s basically magic. It makes your hair feel a bit dirty, which is actually what you want for a messy style.
For the curly-haired guys, the "messy" part happens naturally. Your struggle is frizz. You need to swap your towel for an old T-shirt. Standard towels have loops that catch on hair cuticles and tear them open, leading to a halo of frizz. A T-shirt is smooth. Blot, don't rub.
Then there’s the issue of thickness. If you have incredibly thick hair, your barber needs to "de-bulk" it using a point-cutting technique. This creates channels in the hair so it can collapse into itself rather than poofing out like a mushroom. It’s the difference between looking like a surfer and looking like a 1980s news anchor.
The Cultural Shift: Why Messy is Professional Now
We’ve seen a massive shift in what "executive" looks like. Silicon Valley started it, but it’s spread everywhere. A guy in a well-tailored suit with a long, messy mane looks confident. It says, "I'm successful enough that I don't have to follow your grooming rules."
It’s a power move.
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But there is a fine line. To pull off the long messy hairstyles guys are wearing in professional settings, the rest of your grooming has to be impeccable. If your hair is messy, your beard needs to be lined up. Or, you need to be clean-shaven. You can't have a messy haircut, a messy beard, and a wrinkled shirt. That’s just being a slob. Pick one "undone" element and keep everything else sharp.
Real World Examples and Inspirations
Let’s look at Jason Momoa. He’s the poster child for this. His hair is long, it’s messy, and it’s clearly healthy. He uses oils. If your hair is long, the natural oils from your scalp can’t reach the ends. You have to manually put them back. Argan oil or jojoba oil are the gold standards. Two drops—just two—worked through the ends will keep it from looking like straw.
Then you have someone like Harry Styles during his "Dunkirk" era or shortly after. That was a masterclass in the "Long-on-top, messy-fringe" look. It’s shorter on the sides but has enough length on top to create that signature flop. It’s versatile. You can slick it back for a meeting or let it hang forward when you’re out.
Actionable Steps to Get the Look
First, stop using 2-in-1 shampoo. Just stop. It’s terrible for long hair. Shampoo is for your scalp; conditioner is for your hair. When you wash, focus the shampoo on the skin of your head. When you condition, only put it on the long parts of your hair. If you put conditioner on your scalp, you’ll be greasy by lunchtime.
Second, find a stylist, not just a barber. While many barbers are incredible with fades, long hair requires "sculpting" with shears that many traditional barber shops don't specialize in. Look for someone who has a portfolio of longer styles. Show them a photo. Don't just say "messy and long." One person’s "messy" is another person’s "mullet."
Finally, invest in a wide-tooth comb. Never use a fine-tooth comb on long, wet hair. It’ll snap the strands. Use the wide-tooth comb in the shower while the conditioner is still in your hair to get the tangles out. Once you’re out, let it be.
To transition into this style, start by letting your top grow while keeping the sides tidy for a few months. This "undercut" evolution prevents the awkward "spherical" growth phase. Once the top reaches your chin, let the sides catch up. During this period, use a light-hold cream to keep things directed back and away from your face.
Maintaining the health of the cuticle is non-negotiable. Use a deep conditioning mask once a week if you use heat tools or live in a dry climate. It sounds like a lot of work, but once you establish the routine, it takes less than five minutes a day. The reward is a hairstyle that looks better the less you try to control it.