Charisma, Styling and Context

It’s hard to describe the moment when something makes a powerful impression on you. Little details get lodged in your head. Small things stand out and are suffused with resonating emotion. Motivations are born, and new possibilities revealed.

About a year ago, I saw a guy at work wearing a pair of cropped wide-leg pants. I don’t know what they were exactly, something like a classic Dickies work pant, with a relaxed comfortable rise and a straight roomy leg. 

There was a moment when this guy turned to talk to someone and the loose hem of the pants shifted in a draping way against his ankle. That was the moment. 

I had noticed pants getting wider in the last few years, but I couldn’t see myself in them. I graduated from high-school in 2005, just as skinny jeans and slim fits were coming to dominate menswear. I spent the next decade fully adopting, absorbing and internalizing that look. 

When wider pants started coming back, I thought it was going to be the first in a series of changing trends that left me, and my slim jeans, in the past. My version of a dated old man would be limping around with skinny jeans and a cane. 

But then I saw these Dickie-like pants and something shifted. In hindsight I can see that it wasn’t just the pants. It was the suede Sambas, the perfect pair of socks, and the outgoing personality of the guy wearing them. But in that moment, what stood out for me was the drape, the shifting fabric at the ankle. It just stuck in my head. A few weeks later I was out shopping, trying to find a pair to try on. 

Every once in a while we see someone wearing something and it looks so cool. We are seized by a desire to have it and participate in it, to be that essence of coolness that we’ve witnessed. 

I’ve had several of these experiences over the years, and they all seem to share a number of common ingredients. In this post I want to explore those ingredients and consider what they can tell us about style and our own clothing choices.  

Ingredient 1: Charisma 

There’s a magnetism connected to certain people that is related to confidence, authenticity and ease.

When I was thirteen, my friend showed up at school with a bright red fleece sweater. That’s the first time I remember seeing someone else wearing something and wanting it passionately. After some nonchalant probing, I learned that his mom had made it for him. Somehow I figured out how to source something similar. I don’t remember how, but a week or two later I showed up at school with basically the same fleece. 

This friend was cool, popular, and friendly in a natural way. Because he had two older brothers, he knew about music that nobody else had. His parents owned a motel that became our place to play street hockey and listen to music in unused rooms.

It wasn’t the fleece I wanted. What I wanted was to embody that person in a small way. 

Ingredient 2: Styling 

By styling I mean how a piece of clothing is worn as part of a whole outfit. It is easy to mistake style for collecting and wearing good individual items of clothing. But when we’re impressed by what someone is wearing it is usually by how items are combined, intentionally or unintentionally, to produce an overall impression. The best pair of pants can look silly or awkward with the wrong jacket or shoe. 

Ingredient 3: Context 

Clothing is perceived in relation to the broader context or situation in which it is worn. Examples of context include whether the wearer is old or young, or in a formal or casual environment. Powerful impressions usually involve the clothing relating to the broader context in a pleasing or interesting way. Usually this means harmonizing with the context and associated norms and expectations, but it can also include intentionally contrasting with those expectations. It’s easy to spot when this goes wrong, especially with formality. Wearing a suit in a casual office can come across as pretentious or overly fussy. 

There’s a final ingredient, but I struggle to find a good term for it. It’s the ability for you, the viewer, to project yourself into that combination of charisma, styling and context. You have to be able to see yourself in it. This is a bit counterintuitive as many people don’t have the obvious charisma that we tend to admire in others. 

What’s necessary, however, is not a realistic projection, assessing objectively that we have a matching swagger and style. Instead, we just need to feel an element of comfort and familiarity, enough to let our imaginations wander in that direction. If we don’t identify with something in the look, we’re intimidated by the wearer, or we’ve been told that we can’t “pull that off”, a gate closes in our mind and the leap of imagination does not occur. 

This information is useful in a few ways. 

Brands know about this experience and are constantly seeking to produce it. It motivates us to buy things. Understanding our motivations can help us guard against manipulation, to assess our impressions instead of reacting to them. 

Styling can be learned, practiced and improved. It’s extremely satisfying to learn how important styling is (and how many mistakes you’re making), and then to improve what you’re doing. The confidence that comes after having learned and improved is much greater than the confidence that comes with ignorance. 

And while we don’t all walk around with movie star swagger, we can be thoughtful about the energy that we do give off, and use that awareness to make intentional choices. 

This doesn’t mean that there is a formula for your outfits or style. Surprising and contrasting combinations can produce some of the most interesting and impactful outfits, like young people dressing old, or vice versa.

The idea of someone not being able to pull something off is dumb. Whoever is saying that should interrogate themselves to understand the assumptions that underlie the so called rule, and why they are invested in enforcing it. By being aware of our own kind of charisma, and our context, we can play with expectations, impressions and perceptions intentionally. Ultimately, it’s up to you.

If you’ve got a story about a powerful impression, or a perspective on this topic, feel free to share in the comments.