By Mike Ingram

My father told me once that he missed the way I used to dress. “You always looked so sharp. Like a young Republican.”

I don’t remember what I was wearing at the time, but this would have been the early 2000s, a sartorially confusing era. I was a couple years out of college, waiting tables and trying to figure out what sort of person I wanted to be, an uncertainty that shows up in pictures from those years. In some, I’m dressed for a Phish parking lot, in baggy cargo pants and floppy bucket hat. In others I’m wearing distressed jeans and Western shirts with pearl snaps, and in still others I look like an extra from the movie Swingers: shiny, spread-collar shirts, gelled hair, patent leather shoes. I’d taken to wearing a couple sterling silver rings, and for a brief period I may have owned a puka shell necklace, but the less said about that the better.

I’d never been a Republican, young or otherwise, but I knew what my dad meant. I spent much of my childhood in Charleston, South Carolina, where preppy fashion was so ubiquitous, I never thought of it as a style, per se, but just how clothes looked. In middle school, even the surfers and skaters wore khakis and polo shirts, though they might pair them with Vans or Airwalks instead of Topsiders.

In Charleston we lived in an upper middle class neighborhood, but we were recent arrivals. My father had gone to the Naval Academy largely because his parents told him there was no money for college; his subsequent career in the submarine force gave us a lifestyle that improved in regular increments as he rose through the officer ranks. Our furniture got nicer. We stopped putting things on layaway. My parents dabbled at buying original art. Looking back, I can see that they were studying our new neighbors for clues about how to live, the same way I studied the cooler boys at school, whose preppy clothes seemed to hang more naturally from their bodies than mine did. I spent a lot of time tugging at my waistband, tucking and re-tucking my shirt, trying through great effort to create the easy, rumpled look they seemed to pull off so effortlessly.

When my father wasn’t wearing a uniform, he favored shirts by Lacoste and boat shoes without socks. When company came over, we ate in the dining room, and unless they were close friends my parents would pull out the china and the real silver, always a pain because these items had to be washed by hand. After dinner my dad would offer our guests a snifter of the brandy he kept in a crystal decanter on the sideboard, though he rarely drank it himself, having purchased it, I think, out of some vague notion of “things rich people do”—like listening to classical music during dinner or subscribing to Smithsonian Magazine—before discovering he didn’t have a taste for it himself. Our guests didn’t, either; most of them would opt for bourbon when they learned that was also on offer.

There’s a picture of my father and me that I keep pinned to the cork board in my office. We’re on the back deck of our Charleston house. I must be in seventh or eighth grade. My dad looks fit and handsome in his dress whites. I’m wearing a navy-blue blazer with gold buttons, a striped shirt, and a club tie printed with tiny crests: the perfect little prep.

There’s a timeless quality to the photo, owing both to my father’s military uniform and my preppy one. If not for the Volvo in the driveway, you might be hard-pressed to identify the decade in which it was taken. In The Official Preppy Handbook, the 1981 best-seller that poked fun at WASP culture while simultaneously documenting it in impressive detail, this phenomenon is referred to as “consistency,” a core preppy value:

“Generation after generation will dine, walk, decorate, vacation, work, get educated, get married, and name babies all in the same way. Children perpetuate the tradition because they haven’t been exposed to any other way of life. This primary value ensures that the Prep life will remain intact, that future generations will know which fork to use.”

I know my dad has a copy of the same photo in his study, and I suspect it’s one of several he had in mind when he made his “young Republican” comment. Though I don’t think that comment was about my clothes so much as what those clothes represented.

Around the same time, a college friend who’d moved to San Francisco returned home to Richmond with an eyebrow piercing. “That thing,” his father said. “Does it have some kind of special meaning?” My friend had already come out to me, but not to his parents, and he interpreted the question as being about the question mark of his sexuality. I don’t think my dad suspected I was gay, but his comment did have something to do with his idea of what a “normal” man was meant to look like. I think he was nervous that I’d veered away from the path laid out for me, and that if I wasn’t careful it might be difficult to get back on track. Partly his concern was pragmatic. We were comfortable, but we weren’t trust-fund rich, so if I wanted the upper-middle-class life my parents had enjoyed—and why wouldn’t I?—I’d need the sort of career that could support it. But it was also, on some level, about appearances. You could only tell your friends and neighbors that your son was “finding himself” for so long before they’d start whispering.

As a kid, I told people I wanted to be a lawyer. I saw lawyers on television, but also in our Charleston neighborhood, where they drove Saabs and late-model Mercedes and on weekends wore Nantucket Red pants and the kinds of loafers that could transition from a Boston Whaler to one of the sit-down restaurants along Shem Creek. During ninth-grade career day I got to talk with one of these men, the father of a classmate. He was wearing a navy-blue suit and repp tie, and his face was puffy in a way I would later learn to associate with problem drinking. “Do you like paperwork?” he said. “That’s mostly what the job is. A hell of a lot of paperwork.”

After that I started telling people I wanted to be a writer. Actually, I probably said journalist at first, because that sounded like a respectable career, rather than a vague artistic ambition. But the idea of law school would rattle around in my head for years. I’m sure that’s true for lots of former English majors, but in my case, it wasn’t a career change I was imagining, but an alternate life.

In my imagination, that life had been running parallel to mine all along, so that all I had to do was jump from one track to the other. In that life I moved back to Charleston and took a position at a small firm downtown, the kind with offices in a historic house, preferably down a cobblestone street. I never gave much thought to the kind of law I’d practice; this was an aesthetic fantasy, not an intellectual one. I pictured the tan suits I’d wear in summer. The frayed khakis and boat shoes. I pictured a tasteful house with a dock stretching out into the creek, where I’d sit in the evenings with a bourbon, watching the sun go down.

I’ve always associated preppy clothing with a certain kind of masculine ease. It isn’t about money, specifically, except in the way that not needing to worry about money is a useful precondition for the kind of comfort I’m thinking of. A comfort in one own’s skin, and with one’s place in the world. As a kid I saw that ease in the cooler boys at school, who never seemed anxious about where to sit in the cafeteria or who to talk to on a field trip. At school dances they’d walk right up to one of the popular girls during the first notes of a slow song, armed with a confidence they’d learned in weekly cotillion classes. They were from Charleston, whereas our family only lived there, and that rootedness was something else to envy. I always knew the Navy could move us without much notice, which added another undercurrent of anxiety to my adolescence.

I asked my mom once why I didn’t have to attend cotillion and she laughed. Apparently, that was a bridge too far in terms of fitting in with the neighbors, though my mom also cared less about that than my dad did. “Cotillion?” she said. “Good lord. What century are we in here?”

In The Ultimate Preppy Handbook, author Lisa Birnbach writes that preppy kids, upon entering college, “will discover that what to them had always been Just Clothes is in fact a distinctive look.” I had this revelation a bit sooner, when we moved to Florida after my sophomore year of high school. There were preppy kids there, too, but at my new school I found enough diversity of style that my clothing choices suddenly seemed to carry more narrative weight.

I remember the girl who sat next to me in AP American History, a punk/goth type whose hair color seemed to change every few weeks. We developed a friendship of sorts, making fun of our teacher’s tendency to drift off into stories about her Greek heritage, though I’m not sure we ever spoke outside of class. One day I mentioned Nirvana—this would have been around the time of their MTV Unplugged performance—and she made a scoffing sound.

“What?” I said.

“God, even the jocks and preppies like them now. It’s kind of sad.”

I tried to prove my street cred by naming other bands I liked. The Pixies. Dinosaur, Jr. But she’d made up her mind about me. Then again, hadn’t I done the same? I can see now that our daily banter was flirting, but back then I never would have admitted, even to myself, that I thought she was cute. I was still pining after the girls I’d been trained to pine for, the ones who wore corduroy skirts and grosgrain watch straps and rubber moccasins from L.L. Bean.

It would take me a while to fully get over that. In my late twenties I spent a couple months trying to win over a woman who’d gone to a fancy boarding school and drove her father’s old Porsche. We didn’t have much in common, aside from an appreciation of J. Crew and gin and tonics, but I wouldn’t realize that until several weeks after she dumped me.

The idea of “normal” is all about expectation: what we expect of the world from day to day, but also what’s expected of us. The whole appeal of that preppy “consistency” is that it provides a roadmap for how to live. Your father was a lawyer, or a doctor ,so you become a lawyer or a doctor. You went to Ashley Hall or Porter Gaud, so of course you’ll send your kids there, too. Your family has lived in Charleston for generations, and why would you ever go somewhere else?

I’ve long since lost touch with my Charleston classmates, though the internet suggests most of them have slotted into the lives that were expected of them. On Facebook and Instagram they wear preppy outfits to cocktail parties and oyster roasts. They pilot their Boston Whalers through Shem Creek. They vacation in Duck, or Pawley’s Island, where their families pose for sunset portraits on the beach, their wives in Lily Pulitzer, their kids in miniature versions of the khakis and polos we wore as teenagers.

Sometimes I still feel a tug of envy when I look at those pictures, but I remind myself that I don’t know what their actual lives are like beneath the glossy veneer of social media. I remind myself that the masculine ease I saw in those neighborhood dads was often an illusion. There were affairs and divorces and bankruptcies. I remind myself that no one gets to live completely free from strain and worry, because that’s what my law school fantasy was always about—not about being a lawyer, or moving back to Charleston, but a fantasy of escaping my own anxieties, my restlessness. It was about a life in which I don’t second-guess all my choices, in which I feel rooted to a place and a set of circumstances and happy to be there.

Bio:

Mike Ingram's essays and stories have appeared in publications including The North American Review, Phoebe, and EPOCH. His first book of creative nonfiction, NOTES FROM THE ROAD, is forthcoming in Winter 2021 from Awst Press. A graduate of the Iowa Writers Workshop, he now lives in Philadelphia, where he teaches writing at Temple University and co-hosts the Book Fight podcast. He's also a founding editor of Barrelhouse Magazine, and currently serves as its books editor.

Check out the rest of the 2021 essay series:

Zoom Face by Marcelle Heath
Exuviae by Paul Hile
Normal Between April and May of My Ninth Year by Bridget Brewer
Normal Routine by Thao Votang
Introduction from our 2021 Curator