Recently, I took a trip with my wife to Budapest. On our way back to the States, we stopped in Germany. At the terminal, we sensed we were in the presence of Americans. Did we see their blue and gold passports? No. Did we hear them speak and recognize their accents? No.
What gave it away was their clothing—it didn’t quite fit their bodies.
I’ve worn ill-fitting clothes over the years. Sometimes it was comfort and casualness winning out over style—note today’s trend of wearing workout gear everywhere. Other times it was apathy. Finding good clothes takes effort, and I wasn’t always convinced it was worth it. I’ve also quietly rebelled—former punk skateboarder here—believing clothes were superficial markers of worth, only relevant in job interviews or formal occasions. I now believe none of these are good enough reasons.
The Europeans we encountered weren’t necessarily wearing high fashion. But their clothes matched their bodies. They didn’t let comfort eclipse style.
What intrigues me is this: in our body-obsessed American culture, we’re surprisingly disconnected from our own physical presence. In athletic contexts, we’re actually quite skilled at reading our bodies. In martial arts, for instance, you learn quickly how to adjust techniques based on your body type and that of your opponent. To land a kick, you must instantly gauge the right distance. To throw someone, you must match your center of gravity to theirs. We know our bodies well enough to do these things automatically—because if we don’t, we get kicked or thrown.
Yet somehow, we ignore our bodies when choosing what to wear. I have a thin torso and long arms, and I used to buy large long-sleeve shirts without thinking. The sleeves fit, but I was drowning in fabric. Eventually, I discovered that medium shirts sometimes work—and that the invention of “slim fit” was a small miracle. Same label size, different effect. I suspect many people settle, like I did, for what’s “close enough.” But the stakes are higher than we think.
Beauty makes a difference. It shapes how we experience the world—and how others experience us. Wearing well-fitted clothing can change how people respond to us and how we feel about ourselves. Street photographer Bill Cunningham once said, “Fashion is the armor to survive the reality of everyday life.”
Some philosophers have claimed that one condition of beauty is “fittingness.” But we often think of beauty only in its loftiest, most exceptional forms—movie stars, runway models, unforgettable landscapes. Yet beauty is everywhere, in varying degrees. Sometimes, beauty is as simple as two things fitting together well. For men, this often comes into play when wearing a suit. The jacket, tie, and shirt shouldn’t be randomly selected. Do the pieces work together?
Not everything needs to compete for attention. A sense of balance is essential. If you’re wearing a vividly colored shirt, perhaps your pants should be more muted to avoid visual chaos. These aren’t hard rules, of course, but they’re worth considering. Dressing oneself is an art. Sadly, it’s a diminished or underdeveloped one in many people’s lives.
Some will say good fashion costs too much. But that’s not entirely true. Yes, there’s a real cost difference between off-the-rack and tailored clothing. Still, much of what I’m talking about comes down to understanding your body in relation to two main things: fit and color.
Another condition of beauty is radiance, in which color plays a central role. Radiance is when the beautiful shines before us—when it invites us to keep looking. Clothing should allow your skin, eyes, hair, and personality to shine. Some garments dull a person’s features or highlight their less flattering traits. Others light us up, making us look more vibrant, more ourselves.
Beyond cost and apathy, another reason people struggle with clothing is the belief that if something looks good on some people, it will look good on everyone. This is false. It’s important to pay attention to trends, but fashion’s superficial churn can be cruel. Good, beautiful people can fall behind—or never quite fit into—the latest trend. Advertising thrives on the illusion that we’ll look like the models. It’s not wrong to want to look good. But that doesn’t mean every trend is for everyone.
This is where the art of dressing comes in. It takes trial and error (and lots of error!) to discover what works for you. As you become more attentive, you’ll realize some colors just don’t suit you. Some pants, skirts, or shirts just don’t work. It depends on your exact skin tone, height, and build.
The internet makes this process a little easier. You can find plenty of tools for understanding your coloring and clothing needs—like the “Color Me Beautiful” system from decades ago. We often oversimplify skin color, especially black and white. A simple example: people with cool undertones tend to look better in silver, while those with warm undertones look better in gold.
So—should you get rid of all your clothes? Probably not. (Maybe?) But some serious changes might be in order. Once, fully frustrated, I got rid of every pair of pants I owned and replaced them. And it made all the difference—pants that fit properly can make you feel like a new person.
One last classical condition of beauty is “wholeness” or “integrity.” This one’s a bit abstract: it refers to how closely something approaches its ideal form. There may not be a perfect outfit, but we’ve all seen someone whose clothing seemed perfectly assembled—not flashy, just complete.
On the flip side, we’ve all seen someone and thought, They should’ve worn different shoes or That necklace doesn’t work. Sometimes it’s just a small thing that’s off. We might not know exactly what’s missing—we just know something is.
So, what’s the takeaway? I admit I can be too critical of people’s fashion choices. I’ve studied philosophies of art, beauty, and aesthetic experience. And I used to not care much—now I’m committed to becoming a well-kempt man. But I’m still not a fashion model. I’ve made plenty of bad purchases. You find a shirt you like, it’s not your size, but it’s on sale—and you convince yourself it’s “good enough.” Then it sits in your closet, unworn. Or worse, you wear it, and it looks off.
Philosophers have long told us to “know thyself.” I think we can apply that wisdom to our bodies—and our closets. Looking good requires effort and self-acceptance. It takes effort to find what truly works rather than settling. And it takes acceptance that some garments, no matter how cool or stylish, just don’t look good on us. We need to understand our own proportions—what colors and cuts suit us best. And we might even consider how beauty’s classical conditions—fittingness, radiance, wholeness—can serve us in daily life.
I’m not longing for the strict clothing codes of Downton Abbey. But I do believe people should care how they present themselves. And that begins by learning to see—and dress—our bodies well.
Ultimately, fashion is fleeting. Style endures.
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