My Long, Sometime-Perilous Journey to Grown-Man Shaggy Hair


Grown-man shaggy hair is a thing I’ve wanted to try my whole life, and a thing I’ve consistently chickened out on. “This time I’m doing it,” I’d tell myself, “this time I’m coming for that Kit Harrington spot,” and I’d let it go for two months, reach the awkward stage, and give up. The sides would puff out and make me look like a founding father, or the summer humidity would give me a Richard Simmons effect, and I’d run back to my barber for the old reliable high-and-tight. But a year and a half with no barber has offered us all an opportunity to grow it out, to try something new, to transform in isolation. I had to take this once-in-a-lifetime chance. (I mean, I literally did not have a choice; I can barely line up my sideburns on my own.)

But now, a year and a half in, I look like a member of Journey in 1978. There is potential on my head, but it is a mop. And though our road to the Time After Covid is full of sharp turns and switchbacks, we are eventually going to get back to a fully in-person world. At some point I’m going to have to show up for a meeting where I can’t fix my hair in my own bathroom right before. One of these days, I’ll be in an office in all three dimensions with no access to a hat. Someday soon, I’ll have to answer two very important questions: what the hell is going on up there, and what am I going to do about it?


Dev Patel, shaggy king.


These are questions I am not qualified to answer on my own. So I enlisted the help of a Los Angeles stylist named Kristen Shaw, who is having to shepherd a lot of guys through this stage. And like me, she suspects some shaggier men’s cuts will be the look in the After. “So many men who typically get their hair cut every few weeks suddenly couldn't,” she says, “and the great part about that is having more hair for your hairstylist or barber to play with once things have reopened. And if you have a good head of hair, keep it until it goes away.” So now you have a choice: “You might decide you’re not a long-haired guy and go back to your classic cut, or you can finally really go for that stylish longer look. But how do you know if you can wear long hair until you try it?”

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I choose to be daring. The trouble is, I’m a middle-aged man now, and my hair is greying. I like the color, but the texture is not what I’m used to. “When the hair starts to grey,” Shaw says, “its texture can become more fuzzy or wiry.” And with longer hair on an older guy, shaping is important. For every smooth Dev Patel red carpet photo, there is a Nick Nolte mugshot, for every rakish ‘80s Graydon Carter, a present-day Graydon Carter who looks like he combed his hair with a rake. “I like a good, shaped, shaggy look, one with purpose. If your hair looks unkempt, it can easily go from cool guy long hair to someone who could look like he's trying to relive his youth,” she says.

The secret, when you finally do get back into the chair, is what you already know— clean it up around those ears, tidy up that neckline, even out your lengths— plus something you don’t: micro-trims. Have your barber get into the area Shaw calls “the horseshoe,” the curved part around the crown of your skull, and take out some of the volume. You’re not taking length out of that area so much as you are weight. This will tame the wiry hair in that area that grows out, at a 45-degree angle from your head, allowing the longer hair on top to lay down a little better. Micro-trims: ask for them by name.

Brad Pitt, flow master.


As you grow it out, Shaw also recommends investing in a good shampoo and conditioner. “Start with the base, because it really does affect how your hair strand dries,” she says. And as it dries, “I know it sounds like a weird thing to suggest, but put a hat. Don’t wear one all the time, because it can suffocate the follicles, but as it dries, it’ll be sat way closer to your hair and you won’t have to worry about it going wild. It’s like when women pin their hair and sit under the dryer.”

Haircuts will become less frequent as you grow your hair, obviously, but a few trims along the way are important. “A tidy up, especially around the sideburns and neck is a great way to keep longer hair feeling stylish, no matter what the length.” See a barber for those micro-trims every couple of months, talk to a proper stylist every six months as the new look evolves. Product-wise, stay away from the heavy stuff that you relied on to keep your short hairstyle in place. Shaw says, “I love a great workable cream, or things like texture sprays to keep the hair from feeling fluffy. Broken in and effortless is always the way to go with long hair.”

Kit Harington, duke of curl.


After a session with Shaw, a little regulation in the shape department, and a game plan moving forward, I’m feeling less Journey and more Jon Snow. It may not last forever, but it’s a midlife style swerve I’m proud of. Going a little shaggy is a bold move in middle age. But it’s also a way to wrestle a victory out of a terrible time in history, a way to snatch back your power after having to give it up for a year and a half. Shaw agrees, “In a lot of ways we have each individually been challenged by this past year and a half, and it's brought a lot up as to what is valuable in your life. Whether you keep long hair or you chop it off, adopting a mentality with your hair routine that’s full of confidence in exactly who you are will give you an aura of indestructibility as the world opens again.”

Damn right.

John Mayer, shaggy shredder.


This story originally appeared on Minor edits have been made by the editors.

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Dave Holmes
Dave Holmes is Esquire's L.A.-based editor-at-large. His first book, "Party of One," is out now.
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