Clothing and Character

We frequently discuss clothing here–timeless style, function over fashion, style icons, back to school basics–but more often than not, we’re circling the issue of how your clothes reflect your values.

What I don’t know is if we’ve ever explored this angle: do clothing choices come from certain (Old Money) values, priorities, and habits? Or can donning a new wardrobe (button down, blazer, khakis, penny loafers) influence your values?

Can this process work from ‘the outside in’? Or is it a requirement to first learn, by early experience, schooling, or self-education, the moral constellation that informs the Old Money way of life? and then, quite naturally, gravitate towards clothing that more accurately represents the new, inner person that one becomes?

Napoleon once said that a man becomes the creature of his uniform. Is this an example of ‘working from the outside in’?

And how do prep school uniforms figure into this calculation?

Can clothing work as ‘peer pressure’ to contour behavior and shape choices?

Can dressing like a reliable, modest, polite, and hardworking person really make you any of those?

On the dubious side: I’ve advised probably a dozen young men who’ve come to me, wanting me to help them select a ‘preppy’ or ‘Old Money’ wardrobe as their first step toward reinventing themselves, changing direction, shedding old skin, starting anew. It never works.

A month later, they’re dressing the same way. Acting the same way. Headed in the same direction.

On the plus side: I have watched young people read The Old Money Book and start to work on themselves. They’ve dropped some bad habits. Picked up some pointers. Asked me a few questions. And evolved into a better version of themselves.

Then they circle back, mentioning that they’d like some insights on clothing because the clothes they’re wearing don’t really jive with the person they’ve become.

But that’s just my experience. What’s yours?


  • BGT

19 thoughts on “Clothing and Character

  1. I think people tend to want to wear what they are familiar with, and that affects their level of comfort.

    In regard to style of clothing – I have often noticed families who have little money and dress very casually because, they say, they are not able to afford new things. Over time, it seems, they become “comfortable” with old, worn out clothing. But if a young man, for instance, was given a handsome new suit to wear to an event, he seems to rise to a level of dignity that is charming. I have noticed this also tends to inspire some to higher levels of ambition and goals in life.

    Clothes do have a great impact on our behavior. But one must feel comfortable in one’s chosen style.

  2. Donna Tartt’s novel The Secret History describes a character who tries to leave behind his working class background by dressing and imitating his rich Latin study classmates at an exclusive New England liberal arts college.

    Also, didn’t Thoreau say “I say, beware of all enterprises that require new clothes, and not rather a new wearer of clothes.” In my life I’ve wished I looked more carefully at each enterprise that seemed to say “you need something rather different for this”…not to not try said experience, but to be more fully aware of putting myself up to be changed.

    1. Great comment, Ms. Architect. Yes, we want to avoid ‘posing’ as something just because a new pair of chinos, a button down, and some penny loafers have been acquired and assembled. Remember, too, that Thoreau said whatever he said as the heir to a fortune made by his family, who manufactured pencils, if I remember correctly. If he were alive today, he’d probably caution against the acquisition of new clothes just the same, probably wearing an Oxford cloth button down, chinos, and a button down collar shirt. Yes, let’s transform ourselves, and our wardrobe will surely follow. – BGT

  3. Good day to you Byron,

    Picking up on an extract from your piece: ” Can clothing work as ‘peer pressure’ to contour behavior and shape choices ?”

    I know a lady who is a retired school teacher. During her career she taught high school, primary school, boys only, girls only, co-ed and even special-needs children. The whole spectrum. She told me that if for example she took a class on an outing to a museum or theatre and they all wore their full school uniform they were disciplined, walked in single-file and were well-behaved, especially when using public transport such as trains.

    But if she took that self-same class on the same outing and they were allowed to wear civvies, they were ‘a handful’ to control. There is something about a uniform that maintains ‘uniformity’. I am not certain what it is because from my own experience of wearing them, it is not enough to just ‘wear’ them. They also need to be maintained. Buttons need to be sewn on the right way. Shoes need polishing etc etc.

    Two of the most famous ‘All Black’ rugby players of all time, ‘Hollywood Stars” – one was the captain – arrived at a team practice in the wrong T-shirts. The coach said to them: ‘ Go back to your hotel and put on the correct kit. You’re in the All Blacks now’.

    I imagine it is probably like any enforced discipline. If correctly applied, it is designed to give way to self-discipline and therein the world might fight a ‘better’ person than they might have had that discipline (not) been applied.

    I do agree with Mrs W in her example above of the chap who is given a suit to wear and he promptly adjusts his dignity, upwards. I have seen it. I suppose it is a question of rising to the occasion.

    Perhaps there is a link between all this. After all, one only has to look at the way people are dressing nowadays and then tying it to average ‘behaviour’. Words like abysmal come to mind.

    To me there is a link. And it is very direct.


  4. I look at clothing in terms of deportment. Given my current state of unemployment my current uniform are Khaki’s and Lacoste tennis shirts with my Sperry topsiders. They are old and comfortable. We had our son in a private school and the kids looked sharp in their uniforms, but the curriculum was dreadful so we found a great public system. When I walk my wife’s Pomeranians to the bus stop so they can see my son off to school, I noticed all of the kids wear clothing that have a weird H type symbol on them (including my son), the brand is Under Armor. I protested this to my wife and she told me: “He has classes in French and Violin 5 days a weeks, so get over it”. I guess it’s a balancing act. The only suit brand I wear is JPRESS, then again my job coach told me not to wear a suit to interviews. it gets confusing.

  5. Hello, Byron
    I do believe peer pressure plays a large part in people being able to transform. Birds of a feather…
    This is why when people lose weight they lose their friends. This is why when some people start to make more money they lose their friends.
    Refusal to change can be just as hard of an adjustment as changing. I have known people who refuse to do any self improvement then wonder why they are broke and alone.
    If a person is dealing with changing their perceived image whether it is their self-image or how friends and family see them (and unfortunately try to remind them of who-they-are and not to go thinking too highly of themselves) no amount of outward change can take root until that inner monologue can be changed. Each layer of society has its ‘uniform’. Most people cannot physically step into that layer until they can first envision themselves doing so.
    Yes, putting on clothes that are different from what you normally wear CAN be transformative but is that person able to hold on to their transformation in the settings in which they find themselves?
    Perhaps, if not already done, when encouraging people to dress better it would be appropriate to encourage them to find someone dressed like them and to strike up a conversation?
    I believe self improvement should always be encouraged (as long as it IS sincere and that it IS improvement). Every person is taught how to be the person they are today. Whether they are lessons we give ourselves or lessons other people have taught to us either directly or indirectly through observation. If you learned how to cuss you can unlearn how to cuss. If you learned to dress in a hoodie and jeans you can unlearn that and you can learn how to dress like a Paris author.
    It boils down to how willing you are to cling to and keep your new ways. For those who protest, ‘But it’s not me!!’. I say… “Not yet but it CAN be you if you are willing to be uncomfortable while you, and the people around you, adjust.”.

  6. It starts from inside. Your clothes are an outward manifestation of who you are, how you see yourself and how you expect to be treated. Your character and your choice of clothing are influenced by your background, your family and your education. Your clothing choices reflect your values and principles. But clothing can also be self-reinforcing. It reminds you of the type of person you are, what your values and priorities are and how you conduct yourself. Dressing like who you are makes it easier to be who you really are. So clothing is an outward expression of character and personality which starts from within, but it can also reflect back to you what kind of moral, ethical and social standards you hold yourself to and how you comport yourself.

  7. It is the very unusual and rare person who can quietly recognize personal deficits/flaws, decide to make changes, and (most important) stick to those changes long term. The self-help and dieting industries, among others, depend upon this point. As Amy points out above — though very few want to admit it — background, family, and education (or lack thereof) are primary motivators in all of this. In short, if certain values are not instilled from the start of a person’s life, it is difficult (but not impossible) to catch up 20+ years later. As I began, though, it takes an unusual amount of personal reflection and insight, which makes a lot of people uncomfortable .

    Best Regards,


  8. I believe one of the problems is a lack of expectation. No one is expected to put any effort into appearance because it is not required any more. Comfort has taken hold as the main criteria. You have no idea as to the number of people who tell me, I don’t wear ties because I feel choked, or a jacket is too constricting, something isn’t comfortable. Generally it boils down to either someone isnt used to something and therefore immediately says its uncomfortable, or people buy cheap ill fitting clothes. It probably comes from wearing a coat and tie to dinner as a child, or to school, but it is nothing out of the world to me. A good quality shirt and jacket are never uncomfortable.

    To be completely honest, being able to throw on an oxford and chinos, or a simple well cut navy suit makes my life incredibly easy. I never have to worry about buying anything new to stay stylish, I only replace and upgrade.

    It’s like the chicken and the egg. It is hard to say whether clothes influence the man (or woman), or whether it is the other way around.


  9. Our clothing reflects our life style, habits, values and culture. It’s reflexive and easy for those who come from it. Unfortunately, just wearing a “preppy” outfit does not work because it is self-conscious, and perhaps pretentious.

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