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?