Dressing Well

Although it calls for playfulness, the art of dressing well is a dead-serious matter.

The child is adamant—it is her red-and-pink pony shirt or death. She does not comprehend why the pony shirt cannot be fished out of the laundry for her to wear. Tears run down her face, screams tear their way from her hale little lungs. Though she is young, so-far untainted by the desire to perform clothing for others, still she feels that to wear this rather than that makes an immense difference.

And it does make a difference. The affection which she feels for her pony shirt sets it apart. It is, in the most literal sense of the musty old word, holy. This is what comes before the art of dressing and undergirds it: the holiness. Our outfits can be special. Dressing well means making sure they are.

There is a second thing that undergirds the art of dressing.

Humanity in an evolutionary superstar when it comes to sweating. By dispensing with coats of hair, fur, or feathers and exposing most of our skin directly to the air, we can use sweat to thermoregulate far more effectively than our nonhuman counterparts. In the tradition of those deepish little pop-science bestsellers, we could name ourselves Homo sudans.

But our ingenious sweating kit exposes us to some downsides, from sunburn to hypothermia. Enter clothing. We have used the strategic donning and doffing of clothing to claim the evolutionary advantages of our sweating superpower without the drawbacks. The clothes are, at this point, no less a part of our adaptive Swiss army knife than our penchant for perspiration itself.

Over the long millennia, we have found other ways to make clothing useful. Pockets for carrying, armor for protection, reflectors for visibility. And so this is the other fundamental precursor to the art of dressing well. Clothing exists to serve practical needs. It can do so successfully or unsuccessfully. Dressing well means making sure our outfits do this successfully.

In the barest, most elemental sense, the art of dressing well is the art of balancing these two primal factors: holiness and practicality.

But, in practice, things are more complicated. There is a whole cultural edifice built on the foundation of clothing. The art of dressing well must take it into account.

The implications of culture for practicality are comparatively simple. First, the cultural milieu determines to a significant degree what is practical. You are unlikely to walk New York City armed with a scabbard or a holster—the practical value of such tools is limited in this milieu. Worse than nil, as you’ll discover when NYPD sees your six-shooter or longsword.

Second, there are cultural pressures which limit your options for achieving practical ends. Backpacks are extremely practical accessories for carrying, but—due to their cultural associations with schoolchildren, tourists, and poorly-dressed office drones—many of us opt for still-handy-but-less-capable alternatives.

The way culture affects the practical side of dressing is the same way that culture affects everything.

But we’ll need to take more time to examine the way that culture influences the holiness side—it’s a bit more subtle.

The hunter-gatherer sews seashell beads onto her tunic, creating a mosaic-like design. Perhaps the motif represents a god or spirit for whom she feels affinity. Perhaps it signals her accomplishments. Perhaps it signifies her membership in a band within the larger troop.

In any case, symbolism has crept in. It is not for pure joy in the beads themselves that she adorns her tunic. That may be part of it. But she also intends to reference something, and her reference can only be understood in terms of her cultural milieu.

The ancient priests and vestal virgins were distinguished by their garb. Confucius advised Yan Hui to “clothe yourself in the ceremonial caps of the Zhou.” Medieval sumptuary laws prohibited commoners from wearing fabrics and colors reserved for the nobility. Unionized coal workers wore red bandanas to signal solidarity.

In all these cases and many more, clothing has had representational value. To wear certain things is to summon certain associations—sometimes even to claim certain roles. Even today, wearing certain items—a police badge, a clerical collar—can, in some situations, make you legally culpable for criminal impersonation. There are subtler examples as well. The way that a black turtleneck evokes a certain kind of intellectual, or the cowboy hat a certain kind of country singer. These associations are always changing, just like the meaning of words and phrases change—but they are no less real for that.

We can thinks of this representation value of clothing in terms of language. The things we wear can, in a nearly literal sense, say something.

Philosopher Charles Taylor argues that implicit in any language is an idea of fittingness. If I tell you, “Good night!” at noon—unless there is some special understanding between us to make sense of my comment—you assume that I’ve made an error. “Night” is simply the wrong word to describe noontide in the language I’m speaking.

It’s the same with clothing. You won’t communicate coziness by wearing a sheer tank top and swim trunks, and you won’t communicate chic uptown sophistication with a suit of medieval armor. The communicative intent and the language you employ must fit.

But beyond the basic level of using the right works, there’s also a more subtle sort of fittingness in language. Virginia Woolf explains it well in a 1908 book review:

The question as to what exactly distinguishes the truth from the falsehood in such a work is a delicate one, and the value of the book depends on our immediate certainty—this is precisely right. We can hardly appeal to any standard but that of our own taste in such matters; why, for instance, does an image like the following satisfy us—“The melancholy sunset, the smell of torn-up seaweed and wet sands, has always remained in my mind as symbolical of a soul’s shipwreck”—when the comparison that follows between the shellfish and the human beings seems altogether forced and unimaginative? “Of such quivering slime we also are made up; and our microscopic realities steep in our living liquids as these creatures in the sea?”

Some images and analogies provoke insight, while other seem to miss the mark. It’s the same with clothing; some garments and combinations provoke the reaction “This is precisely right” and some seem forced and unimaginative.

You might object. You might say that color, texture, and proportion are the keys to dressing well. These cultural associations I’m talking about play, at most, a minor role.

But color, texture, and proportion are the how of dressing well. Cultural associations determine the what. Color, texture, and proportion are your quiver full of arrows, but some cultural architype, or combination of architypes, provides a target.

Probably there are some elements of what we find pleasing in an outfit that are biologically-ingrained. This would be difficult to prove, however, and even biologically-ingrained things are culturally-mediated. Which means that even an outfit with intentionally-combined colors, textures, and proportions, could still fail on the level of cultural language.

For all these reasons, it is impossible to master the art of dressing well without mastering the art of speaking in the aesthetic languages available in your culture. This does not mean that the art of dressing well is nothing more than the art of navigating cultural associations. Quite the opposite.

Everything fresh and new and electric in an outfit requires a bit of the unexpected. And you don’t deliver the unexpected by route recitation of the cultural vocabulary. Like a writer-in-words, the writer-in-clothes inherits a language—but in both cases the best work is done at the boundaries, pushing the limits of that language and innovating thoughtfully.

Therefore, it is important to have taste; taste that is not chained to a single set of cultural associations. Perhaps you have in your mind’s a certain silhouette which you find pleasing just as a physical object. Or, you could have an idea for how to combine elements of various aesthetics languages into a look that is more than the sum of its parts. But, to truly master the art of dressing well, you must have something more than the ability to imitate.

There are two components to taste. The first is a skill: the ability to see.

Before I became interested in clothing, the silhouettes of outfits were virtually invisible to me. All I truly saw was the colors. It took years of absorbing photographs and paying attention to the explanations of pendants before the wires connected in the backs of my eyes and I started to see proportions.

But alongside this skillful sight, taste requires a more metaphorical kind of vision. The knowledge of what you want to achieve. And what is this, if not the recognition that something is special to you? So it comes back to holiness in the end. Although you must understand cultural touchstones, and even master them, you will not master the art of dressing well without some sense of what is special and a desire to realize it.

We’ve done enough work to stakeout a tentative definition for the art of dressing well. It is the art of communicating your vision of holiness, through clothing, within the bounds of cultural association while accounting for the practical ends of apparel.