on dressing well

I recently read a fantastic article in the free press : ‘How to Dress Like a Gentleman—and Why’. In it, he accuses our leaders, politicians, CEO’s as looking like clowns –“It’s easy to say: Who cares? What does dressing matter? But culture, politics, and dress have always been intertwined.”.

If you look back to old photos and videos, people were undoubtedly better dressed than today ¹. Everywhere from politics, to media, to the ordinary person. A certain attention was brought into the way you presented yourself to the world.

Nowadays, you’re more likely to see people dressing down to occasions, walking around in athleisure, or turning upto work in a T-shirt (I’m guilty of this). In some respects that may be fine in your personal life (I’d argue not), but for example at work, that will undoubtedly alter the way one is perceived and therefore treated.

Why dress well? What does that even mean?

Dressing ‘well’ means putting effort and thought into the way one presents themselves to the world. It depends on the context, your personal taste and reflects certain values.

Turning upto a ‘formal’ event undressed, usually signals a lack of respect, or carelessness or poise. You will form vastly different impressions of the person who comes to a job interview in a T-shirt and jeans versus a three piece tailored suit.

Therefore one core value it reflects is attention. Putting in care into your appearance is the start of how you treat everything else. How you do anything is how you do everything of course. Ackerman writes :

There is a difference between getting dressed and putting on your clothes. The former is deliberate; the latter is not. A person who gets dressed is a person who is intentional. It communicates a plan. During the darkest days of the pandemic, when there was no reason to wear anything but pajamas during quarantine, I made a point of getting dressed each morning. This was something I could control

I remember I had to put on a suit and tie to go to school everyday. I think that subtly altered the way I perceived myself - it made me more disciplined, studious, diligent (previously being the complete opposite).

There’s an umbrella concept of ’enclothed cognition’ ²- the way the wearers psychological processes are altered by their clothing. You will act differently and think differently based on the model you’ve created of yourself. So outfitting yourself in a way that reflects your artistic sensibilities or character, likely reinforces that self-model of being that kind of person.

More importantly, it reciprocally reinforces the way we see ourselves. Our sense of self is deeply influenced by what ‘others think of us’ (or more accurately what we think others think of us)- ‘Looking glass theory of self’ ³ . So you can imagine if you are treated a certain way, you act a certain way, and therefore are treated a certain way etc. A worldview forms around this. Clothing plays an important part in how one is perceived.

Why dress well in your personal life?

Well it goes back to attention. There is no divide in your life -personal space, behaviours of mind, aesthetics, I’d argue is not separate from character formation. This goes to even the smallest things. Do you crumple up your clothes and throw them into your cupboard?

Marie Kondo of all people realises this, through bringing back a modern day ‘animism’ - things are alive. The way you treat anything, is how you treat everything. Dressing ourselves is something we’ve been doing throughout human history - there is almost something sacred about the ritual when done intentionally. It can signal ‘I’m entering the day with purpose’ - a way of honouring the transition from sleep to waking, private to engaged.

Moreover modern life constantly asks : what’s this for? The productivity gurus are constantly asking What’s the ROI? How can this help me get ahead in my job/career? (Another post I want to address a deep narcissism in our culture) Tech culture has valorised ’not caring’ about appearance as being a sign of focusing on what really matters (user metrics, time on site, how much AI slop can we churn out - fantastic metrics…).

But instead, this is taking the opposite approach. It says that ’this matters intrinsically’ - Beauty, care and attention - they’re not a means to an end, they’re how we inhabit life with dignity, poise and grace. I love Nabeel Qureshi talking about “care being the opposite of (AI) slop”.

In formal Zen practice, putting on robes (kesa) is itself a practice. The act of dressing embodying the teaching - reminding us - pay attention! It’s all right here in this moment. So dressing, like any activity we do daily, can be seen as sacred. It can become a ritual, another activity to bring care and attention to.

Why do men specifically dress badly or carelessly?

Ackerman in his essay talks about seeing a couple on a date, the woman clearly had put in effort into her appearance, but the guy had done the bare minimum. I’ve seen the same dynamic so many times - the lady has taken the time to dress elegantly, whereas the guy has thrown on gym shorts, a T shirt and trainers. I suspect this is worse in the US, than in Europe.

A few conjectures (I don’t hold them too strongly, just a few theories).

I : A lack of identity. We know men in general are struggling nowadays, falling behind educationally in comparison to women. There’s been reports of a drop in partying, drinking, sex and relationships for 20-30 year old men, replaced instead with gaming, online gambling and porn.

Psychologically men tend to form their identity through what they do, what they can provide. We see this clearly in defined roles such as in the military. Losing that is devastating. Mislaid ambition and testosterone directed instead towards fictional goals, facsimiles of the real thing. Advancing in video games, instead of acting in the world and advancing in mastery/career/skill, indulging in online porn instead of going out into the real world and dating. This is a big step from clothing, but I think a symptom of this disease. When you know who you are, you tend to dress like it.

II: Lack of role models. Currently, when we look to our leaders, we see people who lack poise. I imagine a leader to be like Jean Luc Picard from TNG - dignified, firm, graceful. Not perfect, but clear in his values. Instead, we see leaders engaging in online meme battles, cryptocurrency frauds and lacking any semblance of grace. On the far end, you have people like Andrew Tate, giving young men a completely distorted view of women. This hurts both genders.

III : Extended adolescence. The markers of adulthood (marriage, career, home ownership) have been pushed later and later - and so the aesthetic of adolescence (sneakers, hoodies, casual) extends too.

IV: Putting effort into appearance has been coded as ‘inauthentic’, ‘vain’ or ‘feminine’. Caring about your appearance signals a certain shallowness. But I’d argue that is backward - not caring about your appearance often signals a general sloppiness that bleeds into everything else.

I didn’t expect a post on clothing to become so theoretical. It’s almost counter-cultural now to put in effort into dressing well as a man.

When even our leaders can’t be bothered, when comfort and convenience trump everything else, when we’ve coded care as weakness—choosing to dress with intention becomes a small act of resistance. Not against any particular ideology, but against the general sloppiness, the pervasive giving-up that characterises so much of modern life.

This isn’t really about clothes. It’s about whether we believe being an adult means anything. Whether certain occasions deserve respect. Whether we’re willing to accept any standard that isn’t purely self-determined. The guy in gym shorts on a date isn’t making a statement—he’s just opted out. And when enough men opt out of enough things, you get a civilisation that looks increasingly like ours.