Why grown men don’t want to dress like grown men

On the day I turned 20 I was sitting in my parent’s basement on an ugly tan corner couch they had bought at a furniture warehouse. I was watching TV, not a specific show, just watching TV. I was wearing an old pair of jeans and one of my birthday presents, although I can’t remember who gave it to me. It was a swirling, multicoloured tie died t-shirt with an endless stream of Grateful Dead bears dancing in a psychedelic swirl to infinity. I loved it because it represented joy, lazy summer days and expanding your mind.

My dad, on the other hand, was not impressed. Teddy bears. Suggested drug use. An assault of colour. He sat down across from me on the couch, in jeans and an ill-fitting polo shirt, looked disdainfully at my tie dye and said “You’re a man now, you should start dressing like one.” I sat there in silence, with no reply. He’d never commented on my manliness before and certainly never made an association between clothes and growing up. And it’s not like he wore suits or blazers every day, if ever. Instead of internalizing what he said I just shoved it on that shelf in my head labelled “Stuff Old People Say” and contented myself that my generation knew better.

We knew that we could wear whatever we wanted, whenever we wanted. And not only did we know better than his generation, we were proud of not growing up. We idolized our childhoods, collecting toys, watching cartoons, wishing we were ten years old again. In fact, my extended adolescence lasted well beyond my twenties, into my thirties. And I am not alone, far from it. The generations before and after mine were also encouraged to not grow up. And this attitude has taken root most clearly in how many people dress.

Up until the 1960s in every culture, in every time, boys aspired to dress like men. In fact, most of their clothes were just miniature versions of grown up clothes. Or children’s clothes were specifically and only worn by children, like short pants in England. Then the counter culture movement of the Sixties challenged everything about Western values, including and especially what it meant to be a grown up. Adults were uptight, out of touch. Don’t trust anyone over thirty. And grown ups were the cause of everything wrong in the world, from war to slavery to sexism. Youth was the salvation.

And for the first time in human history, men started to dress like children. Fathers asked their sons for fashion advice. The passing and superficial whims of the young were foisted on the old. For the next few decades, the traditional ways of dress for grown men were stripped away, from hats to suits to shoes. All of it was replaced with what kids had worn: ballcaps, t-shirts and sneakers. I’ve written before on the social roots of this move away from dressing well based in egalitarianism and authenticity. For men, that meant an attack on the uniform of the grown man.

I’ve often heard something akin to this statement: “Mr. Thompson? No, no, Mr. Thompson is my father. I’m just Steve.” It suggests that there is still—even today—a deeply rooted fear in many men of being associated with an old definition of manhood. I will happily concede, however, that in many ways this is for good reason. There were an awful lot of very, very poor examples of manly behaviour in the past. Our history books are full of them. But instead of creating a new, enlightened manhood, many men choose not to grow up but hold on to their youth as long as they could.

So much has been lost and I’m not just talking about cufflinks and collar stays. Our very image of ourselves is based on a flawed model. Children, after all, are not always examples of humanity at its best. Well, children in affluent developed countries at least. They do not take responsibility. They are not resilient. They are not resourceful. Their empathy and compassion are fleeting and unreliable. They cannot easily control their emotions or their urges. And so I feel that when you dress like a kid, you are not only saying “I’m not that old kind of manhood” you’re also saying “I won’t take responsibility for my actions” and “I’m not trustworthy.”

As I write that, I’m aware that when I dressed like a kid, even in my thirties, I didn’t feel irresponsible and untrustworthy. I was still doing my best to be a good person. But I most certainly didn’t feel like a grown up. What that meant for me was that I was missing a belief in myself, in my own abilities, a confidence when I entered a room or a new situation. Since I equated that confidence with overbearing masculinity, I shied away from it. And so while I looked at my dad’s generation with derision from the outside, inside I felt a reluctant admiration for their fortitude and self-assurance.

But the solution to this problem isn’t simply to “dress like a grown-up” because what does that even mean in this day and age? If most men dress like children, does it mean that is the way grown men should dress? We are stuck, it seems, between the rigid uniforms of the past and the inelegant sloppiness of today. However, as I argued about dressing well, we do not have to dress either like grandfathers or like children. For me there is a balanced approach which borrows from the past while being thoroughly contemporary. An example is the joy of mixing our freedom to wear so much colour today (although perhaps not as much at that Grateful Dead shirt) with the silhouette of classic tailoring. Regardless of your approach, the key to dressing as an adult is dressing with intent. Instead of just putting on whatever is around, whatever is sold in the mall, whatever is worn by everyone else, build a wardrobe based on quality, longevity and personal style.

My journey towards building a wardrobe arose out of a desire to put away childish things and accept the fact that I am an adult. Not only accept that fact but celebrate it. I will concede, however, that it’s easier said than done. Being a grown up is difficult, as it should be. There is hard work to be done, work that won’t often be rewarded. Taking full responsibility for your actions requires a constant struggle against inertia and inaction, fear and uncertainty. So before we start looking at our wardrobes, we must first look at ourselves. While I do believe dress can help you become who you want to be, that journey must begin with an internal desire to be a better person. As Hemingway said: “There is nothing noble in being superior to your fellow man; true nobility is being superior to your former self.”

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