Sweatshirts off, shoes tied, shirts tucked, belts buckled, buttons buttoned (including top-buttons and collar buttons, Nate), ties up, collars down: and so we begin the day, looking presentable before morning prayers. The process repeats itself several times throughout the day, sometimes individually—let’s fix that collar, Tom; Rich, hats off inside; Brendan, the buttons on your shirt are out of order, please go outside and start over; do those shoes have leather uppers, George?; Anthony, if it’s made of heavy cotton, has a hood, and a large “V and Sabers” on its chest, it is in fact a sweatshirt, and many et ceteras. A slippery slope, a constant battle, a hearty defense of the dress code is a necessary and worthy fight that must be waged at the desks, in the homes, and upon the campus landing grounds; not only for the sake of the school but for the culture at large.
Before you take me for a thirty-three-year-old curmudgeon decrying the slovenly standards of today’s youths, a modest confession: I like neither ties nor dress shoes. I am most comfortable dressing in a manner that fits more into Boulder, Colorado, than D.C. boardrooms, yet despite my dislike for the nooses we tie ’round our necks every morning, I also recognize their importance, and even their necessity, at this school found in a tony neighborhood a short jaunt up the river (as the crow flies) from our nation’s capital. Further, if you are looking for a tailor or a stylist, I have no preconceived notions that I will hear your knock upon my door—if you can read this short screed on sartorial prudence, then you can dress yourself, your children, and your students well. Since the Fall, it’s in our very nature to cover ourselves with the best available raiment; look no further than post-Fall Adam and Eve, who gathered fig leaves before “the Lord God made for Adam and his wife garments of skins, and clothed them” (Genesis 3:21).
Developing the foundations of a school, of a culture, requires installing strong girders that will bear the weight of a panoply of personalities and individuals to flourish within a community. We do not aim to create blindly docile automatons, but rather free-thinking souls who seek the true, the good, and the beautiful; and just as this can be accomplished in the classroom, so can it be achieved in our dress, for what we put on every day goes beyond mere function or style. It is also an outward indication of human dignity, of who we are, and perhaps, of who we strive to be.
The saying, “Don’t judge a book by its cover,” has good intentions, but it also often lets the book off the hook. A better method of thinking is, “Dress the book so that it’s judged well.” Something that catches the eye without being gaudy, something that speaks to the nature of the book without being preachy. A good example sitting on my desk right now: The Hildebrand Project’s 2017 edition of Dietrich von Hildebrand’s The Art of Living. It’s slightly taller than the typical hundred-page book, so it stands out a little on the shelf, and on the cover, a Winslow Homer painting of a man standing atop a peak in the Adirondacks, one foot slightly higher than the other, at rest. The colors are somber yet bold, several shades of darker green below a deep blue, with a cloudy sky. The title is in black print on a white rectangular field centered in the upper third of the cover. It’s modest, reserved, and elegant, beckoning the eye without giving anything away. You want to pick it up, to find the mysteries that lie within.
On the two polar ends of the dressing equation are uniforms and no standards, and both, like all extremes, are unsurprisingly unhealthy, though I grant that uniforms serve as an easy out, especially for the fairer sex, where dressing for “expression” rises to a level incomprehensible to men. The benefits of uniforms are obvious: they provide a straightforward means of instilling basic standards. It is truly much simpler when all choice is removed from the equation. A gray polo shirt and blue chinos. Boom. Done. Wear it every day, and on special days, pay $2 to wear a different-colored polo shirt. Brilliant! However, aside from there being no joy in it, the total removal of honest expression, and the instantaneous expulsion of shades of color, the children never learn how to dress themselves. They go from their uniforms into Crocs and joggers and never look back until they are shackled back into their restrictive outfits the next day.
This is not to say that uniforms are inherently bad— they have their time and place, such as the sports field or the battlefield, places where, in the heat of the moment, when faces may not be readily seen, it is necessary to see simply the clothes that denote my side versus your side. Sports and military uniforms are, after all, functional, and at their best, also fashionable in their use, though I would posit, never fashionable outside of their intended use. For example, if we could rid the world of camouflage cargo pants and adults wearing the jerseys of men thirty and forty years younger than themselves, we would be moving in a positive direction. And if a school is not prepared, for various reasons, to defend a dress code, then we should consider implementing a more concise one.
In forming a dress code, we should ponder several key ideas. Perhaps most importantly, we should consider the tone that we intend to set. When I started at The Heights as a third grader twenty-five years ago, it was said that boys should dress like their fathers because, like their fathers going to work, the boys’ study was their respective work. And back then, our fathers did mostly dress like us, though an anecdote a colleague likes to share recalls a boy responding, “My dad’s a plumber and wears jeans and dirty t-shirts!” Granted. Yet, if the goal is to have a serious tone, a sense of “study as profession,” then the dress should inform that tone. Though if the goal is to make the school into a home, we may also consider exchanging the boots on a snow-crusted day for a pair of slippers in the cozy classroom, a wood stove burning in the corner. If the goal is an agricultural school, then we would aim for a code that informs hard work outdoors or at a workbench. And, I suppose, if the goal is lounging, then by all means, throw sweatpants and Uggs into the equation.
In much of our decision-making as a school, we should be inspired by our location, as should be the dress code of any school anywhere. Just as it would be inappropriate for a Mountain West school to exceed the standards of “Western Formal,” so would it be improper for an East Coast school to descend below the standards expected in the halls of the Capitol, or the offices on K Street, State Street, or Wall Street. And when those standards begin to falter, then it is the school—deriving from scholéschola, or “leisure”—the basis of culture, that must uphold the standards that look beyond the comfort of strangers to a higher Good. Choose the best of what the parents are wearing to work and run with that. Lately, things have slipped, especially over the past five years since the COVID pandemic, but while an adult who has learned the value of hard work may be able to accomplish great things with shaggy hair and a Hawaiian shirt, most teenagers cannot. So if you’re on the East Coast, request the tie and slacks. If your school resides west of the Appalachians, long pants and a long-sleeved button-down shirt, tucked in, will suffice. The obvious ones: a belt, socks, and leather shoes (the latter can be accomplished well anywhere).
With tone and place now simmering on the back burner, we can consider the occasion for which we are dressing. Steve Jobs famously simplified his wardrobe by ordering hundreds of the same black turtleneck and blue jeans, yet he was a singular force of nature with his own particular predilections that we need not impose on society-at-large. When confronted with an event, the simple answer is to dress slightly better than the common denominator with a firm understanding of the tasks that must be accomplished each day or event. Just as an arduous hike is no place for fashion-forward casual kicks, a cocktail party is no place for flip-flops and shorts. When forming a dress code, we want to consider how our students will be spending the day as a whole so that they do not need to cycle through outfits. A lower or middle school student who receives adequate outdoor opportunities throughout the day will need shoes that allow for football, climbing trees, wrestling, and foot races. Patent leather shoes will be torn up in days; a sturdier pair of shoes is a necessity. If faculty can be expected to join for some of these activities, then wool suits can neither be expected nor mandated.
The trips afield are also excellent opportunities to coach students in dressing well when not at school. In the lower school at The Heights, on our treks to the farm to harvest our classroom Christmas trees, for example, we encourage the boys to wear trousers rather than sweatpants, boots rather than sneakers, and to dress in layers to keep out the cold rather than a down parka better suited for mushing across the Alaskan Interior. On flights, we can raise the tone simply with long pants and a collared shirt, or even a long-sleeved t-shirt with a collared fleece or jacket, depending on where the flight is headed—dress for where you are flying, even dress the part in the place you visit if it can be done without purchasing the Patagonia catalogue when visiting outdoorsy locales. But we would want to avoid dressing the part of a “Dude”; as a good school dress code has room for differing tastes, so does a local dress code. In other words, play the part honestly and skip the ten-gallon Stetson with the tag hanging off the back.
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One’s personality should infuse one’s dress—within a dress code, there should be plenty of space for honest expression. Space for, among others, the “Color Wizard,” the “Glee Club Professor,” the “Mountain Man,” the “Economizer,” the “Lumberjack,” the “Frat Bro,” the “Cool Guy from the Aughts,” the “Coastal Cowboy,” the “Hobbit,” the “Southie Dunkin’ Regular,” the “Suave Sicilian,” and, even, dare I say, the “Twentieth-Century LARPer,” though it would best if the latter were few and far between! It is, of course, key that in expressing oneself through dress, we aim for prudential decision-making in our purchases. Savvy shopping is most likely necessary for life on a teacher’s salary, and for our children, many of whom have yet to develop a sense of style, let alone the ability to keep track of their belongings, it would border on the absurd to buy a cornucopia of nice things that may only end up moldering in the constantly-growing pile of “Lost and (never) Found” items, or, with better luck, in the back of the closet or under the bed. A better option for parents is to really know our children and shop with that in mind: Will he be responsible with this item? Are these his colors? What is his actual pant size? I know he wants Hey Dudes, but do those even fit the dress code? Know your boys, and you can help them dress appropriately and economically.
And don’t forsake the accessories! Just as a good pair of earrings can enhance a face, so can a good pair of eyeglasses on a boy, allowing him even to see! According to a National Health Survey, slightly over a quarter of American children need corrective eyewear. I get the sense that making fun of boys who wear glasses (“Hey, four eyes!”) is not as common as it once was, which is a true positive; however, it is still just as common for boys to wear ill-fitting or downright ugly glasses. Do your son a favor and help him pick a good pair of glasses that fit his face and do not break the bank. Square or rectangular glasses are not for every face, so consider round lenses for some, and frame colors that complement the boy rather than a one-size-fits-all pair that tints when faced with UV rays. We can all then pitch in when we see a good pair of glasses by complimenting the boy on a good choice. This goes for any well-suited kit— dressing well matters, so stick your neck out and toss a few words of affirmation his way. Beyond recognizing good choices, compliments let boys know they are noticed. Especially in middle school, but really at every age, it’s worth it.
After the recent snaffling of Royal jewels from the Louvre, a photo circulated of a well-dressed man who was purported to be the chief investigator of the case. He certainly looked the part, with a fedora, buttoned-up vest, and an overcoat, umbrella in hand, held just-so. It later turned out that he was a fifteen-year-old who dressed with panache, but it set the interwebs aflame with intrigue for a few days, no doubt partly due to the exquisite dress of a teenager. We do have students like this boy at The Heights, but we cannot expect all boys to reach the very brink of fine dress before tipping over into the abyss of vanity and to walk the tight-rope so well. It is best to seek good quality clothes over quantity and take great care of them. Using clothes as a means of teaching responsibility and a proper sense of living the virtue of poverty well kills a proverbial flock with one stone. And put your foot down if his sartorial choices are beyond the pale. No, Jasper, you are not honestly expressing yourself in baggy black clothes, Converse low-tops, and heavy chain necklaces! And, Horace, that trench coat is a bridge too far; let’s go on a shopping date and find you a new warm coat.
A new student rushed up to me at the beginning of the school year with a breathless and tear-streaked lament: he could not find his library book. His hair fell into his eyes, traces of a red, sugary drink graced his upper lip, his glasses slipped down his nose, his tie was askew, his second button buttoned into his collar, the tail of his shirt was untucked, his belt had skipped two loops, his pants were falling below his posterior, and both shoes were untied. He was, by all accounts, the definition of disheveled. I had him catch his breath, and step by step, we re-ordered his appearance. His tears stopped flowing, he took some deep breaths, and in a moment, he transformed from a distressed pile of clothes back into a young boy. Did you check your backpack? He returned posthaste with his book and rushed off to the library at top speed, taking the Portuguese steps that lead out of the Valley two at a time.
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Dressing well and finding one’s fit are not often gifted at birth, but learned and honed as we age. Acceptable styles come and go (and I’m not talking about the warp-speed of TikTok video fashion), and as we discover our interests and gifts, so do we discover what forms of dress best fit each of us. In developing a clear dress code that encourages a heightened tone, without being draconian in style, schools and parents can teach our children how to present themselves well and dress in a manner that befits the very real human dignity ordained by God, who made us in His own image and likeness. Dressing well, having a keen sense of sartorial prudence, is thus a prayer in itself, as we demonstrate our incalculable worth and instill self-confidence through dressing with purpose.