Preppies are most basically those people who don’t mind being associated with elite schools and the professions those schools feed into: banking, teaching, government (and one might add sailing instruction and magazine fact-checking). By virtue of the clothes they wear, they express their comfort being associated with a certain kind of cultural prerogative — one that is particularly suspect right now, in the era of foreclosures and Occupy Wall Street.

Stillman’s movies, from “Metropolitan” to “Damsels,” illustrate bigger ideas about the way preppiness is understood and misunderstood by Americans.

Like members of other subcultures, including Deadheads or Goths or English soccer hooligans, real preppies are at least willing to proclaim allegiances. Some of those allegiances are parochial, and might be represented by, say, a college scarf, while others are broader. But Stillman’s characters exist out of time and out of context. They may talk about politics (a bit), and may worry about how the lower classes perceive them, but they ultimately have almost nothing to say about, or even to do with, the institutions that form preppies: the universities, the banks, the government, even the yachting club. They’re all dressed up with no place to go.

Of course, thinking of Stillman as a preppy filmmaker is an understandable mistake. He is heavily responsible for his own inclusion in the pantheon of prep chroniclers, from J.D. Salinger to Louis Auchincloss, and Lisa Birnbach. His 1990 debut, “Metropolitan,” was the first movie to treat prep culture with a discerning eye after a decade that, despite the rise of Polo and other preppy brands, saw movie preps only as douffi (the plural of “doofus,” according to “Damsels in Distress”). I am thinking here of the Robert Prescott characters in “Real Genius” and “Bachelor Party,” or the golf-club villains in “Caddyshack.”

But “Metropolitan” was a shrewd movie about New York City private-school alumni on winter break from preppy colleges. It’s a movie whose plot hinges on a character’s decision to purchase at A.T. Harris the tuxedo he had been renting — after admitting to himself that if he’s to attend more debutante balls, he realizes he needs better threads — but that same character can have a thoughtful, if pretentious, discussion about Fourier. And Stillman, like F. Scott Fitzgerald, has the wit to give his characters names just a rep stripe away from caricature: “Tom Townsend,” “Serena Slocum,” “Rick von Sloneker.”

As if to further identify himself with prepdom, Stillman has always carried himself as a possible model for his characters. To this day, he meets reporters at the Harvard Club, and even when he is some miles away he still looks “like a wayward preppy trying to get into the Harvard Club” — a look, the New York Times Magazine recently noted, that involves “khakis, a white shirt and a blue blazer.” Stillman did, in fact, attend Harvard, which means that he could get into the Harvard Club, and if he had not attended Harvard he ought to have, being named John Whitney Stillman and all.

That willingness to dress a certain way — even when it might get you attacked by punks, as in “Last Days of Disco,” or called a fascist, as in 1994’s “Barcelona” — is a meaningful tenet of prepdom. But the clothes are not just an aesthetic choice. After all, it’s the rare preppy who does not know that she is wearing a uniform that, if not actually identical with an elite — anyone with a little money can buy the clothes — signals an aspiration toward elite society. To wear clothes made popular by the Ivy League is to announce an affirming attitude toward the Ivy League. That may not be a popular stance to take right now. For good reason, our country’s financial elite is under attack, and the schools that breed that elite deserve some of the opprobrium.

But preppy clothes have been the uniform of other products of the university, too, not just the bankers. Who loves a tweed jacket more than a humanities professor? And who loved a sack suit more than the elegant political radicals of the early 1960s? Take Malcolm X: For him, conservative attire was not ironic but proprietary. His clothes announced that he, and the Negro more generally, was entitled to the uniform and the prerogatives of power. Preppiness, in other words, is not inherently reactionary, and it is not inherently exclusionary; indeed, in a sense it is very democratic, precisely because one only needs the clothes, not a family crest. But it is not demotic; it is elitist. It is concerned with access to hierarchies, not the abolition of them. There have been left-wing preppies, but there have rarely been populist preppies.

In Stillman’s movies, however, preppiness almost never carries this complicated, interesting philosophical baggage. There are movies far less accomplished that nevertheless have more to say about the contradictions of prepdom. “School Ties” examines the anti-Semitism that used to pervade prep schools; “Igby Goes Down,” the nihilism and dysfunction of Manhattan private-school culture; “Dead Poets Society,” intellectual conformity; “Love Story,” the class chasm on Ivy League campuses. “The Rector of Justin,” the 1964 book by the dean of preppy novelists, Louis Auchincloss, depicts a rotten ethical core at the heart of a Groton-like boarding school. These works vary in quality, but they at least treat prepdom as the site of interesting, and often timely, dilemmas. They feature preppy clothes aplenty, for authenticity and because the clothes are beautiful to look at. But the clothes are just the superficial signifier of preppiness; the movies are about much more.

Stillman uses preppy clothes for an entirely different purpose.The clothes round out his characters, give the audience shorthand for what kind of families the characters come from, but above all take them out of time. For Stillman, preppy clothing is not a way to evoke, say, a Kennedy-era boarding school, but rather a way to defeat dating altogether. In short, if you wanted to make a fantasy movie set in some unidentifiable period of postwar America, you could use certain articles from Brooks Brothers and J. Press. And, indeed, that is what Stillman, who is not a realist or ethnographer but a fairy-tale fantasist, has done.

Consider “Metropolitan.” A screen card at the beginning says that it is set “not so long ago.” The characters seem to have late-20th-century diction — they don’t have the quasi-Brahmin speech patterns that persisted in the Ivy League into the 1960s (see the young John Kerry here) — but the yellow cabs are of an earlier vintage. The lapels on the men’s jackets are neither early-1960s narrow nor late-1970s wide. But the cut and the shoulders are not from the 1980s. Like the women’s gowns, the men’s dinner jackets are, in fact, designed to straddle all eras while beholden to none. It turns out that there are few styles harder to date accurately than the clothing appropriate for a debutante ball, or the preppy casual clothes one relaxes in afterward. The mystification of time continues in “The Last Days of Disco,” which according to the screen in the beginning occurs “in the very early 1980s,” but shows footage of the Disco Demolition Night held at Comiskey Park in July 1979.

In all Stillman’s movies, there is no racial or religious tension, no class envy, no religious bigotry. Stillman’s world even lacks many of the interlopers who have kept prep schools and elite colleges vital and meritocratic (and fashion-conscious): There are no obviously Jewish characters in Stillman’s movies, no Asian Americans, only one black character who so much as gets a name, and no gay men or lesbians.

There is nothing wrong with Stillman’s World, this alternate reality in which conversation is snappy, the young men and women are all attractive, and their clothes are tailored awfully well. There are times when I would not mind living there. But that’s because it’s a Utopia, literally a nowhere — it does not exist, it cannot exist. That the resident characters wear certain clothes we associate with certain schools, certain professions, certain vacation spots and certain stores does not mean that these characters are like the real-world people found in those schools, work professions, vacation spots or stores. Whit Stillman characters are not preppies; they just dress like them.

But more than ever, what is true of Stillman’s characters may be true of anyone wearing preppy clothing in America today: He is not exactly a preppy. It’s not that he lacks money or schooling — after all, the majority of preppies were always aspirational, rather than bred. It’s that the statement he is making has nothing to do with elite institutions or power. In fact, preppiness today is a way to avoid those conversations.

To wear such timeless clothing in 2012 is a bit like wearing very preppy clothing in 1970, when Whit Stillman was in college. Outside the haberdasher’s doors, there is warfare, recession and class anger; but on one’s back there are the clothes of another era, indeed clothes that transcend all eras. In a time of tumult, preppy clothing is escapist. It does not imply that its wearer is a conservative or a 1-percenter or opposes birth control for women. But it does suggest that, at least for the moment, he would rather talk about something else — as if it were a few years ago, or a few years from now. As if talking about something else were ever really possible.

The hoodie is not the most vilified garment in American history — that can be gauged by the fact that no member of Congress has shown up to work in a burqa, along the lines of U.S. Rep. Bobby Rush’s hoodie stunt last Wednesday. In the past century, the lineup of suspicious clothing has included trench coats, jeans and stiletto heels. And they are all presumed innocent until proven guilty.

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When you find out he is a man, does he become less beautiful? If so, does that challenge your thinking about beauty?

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Jason Wu is the young, impeccably elegant designer whose career went into the stratosphere when high-profile Michelle Obama chose his dreamy, one-shouldered creation for her husband’s inaugural ball in 2009. His preppy-with-an-edge ready-to-wear designs retail at high-end stores like Neiman Marcus and Nordstrom for upward of a thousand bucks a pop. So from the moment Target – which has in the past done wildly successful collaborations with the likes of Alexander McQueen, Jean Paul Gaultier and Rodarte — announced that it was teaming up with Wu for a February launch, the slavering began. And when Target released a preview teaser of zippy little navy and cream ensembles, we all pretty much knew: There would be blood.

Sure enough, there was. Across the land, you could hear the cries of disappointment as the entire collection was snapped up before most of America had brewed its Sunday morning coffee. In some quarters, it got downright ugly. In Miami, a couple cleaned out the entire line “in two minutes.” Store security was called to intervene, the mob turned angry, and one of the Wu vultures allegedly taunted the other shoppers by saying they could “buy it off him outside.”

I’m a fan of Wu’s cool, ladylike and eminently wearable designs, and, as it happens, live near a Target. And because I usually swing by the superstore after my Sunday morning run anyway, I figured this weekend would afford an opportunity to at least check out the Wu wares. I assumed it wouldn’t be crazy there, because believe me when I say that the Bronx Target, conveniently located near the Applebee’s and that guy selling incense on a card table, is not exactly the fashionista Mecca of Miami.

It was not yet 10 in the morning on the line’s launch day when I entered the store. What I found was a scene of devastation unlike anything I’d since, oh, Filene’s Going Out of Business sale in December. The entire accessory line of cute purses and scarves was nowhere to be found. And the handful of racks that had held the promise of cap-sleeved blouses and pleated skirts was picked as clean as a cow carcass in piranha-infested waters. The real pros had likely cleared off moments after the store opened at 8. But around the racks, there still hovered a group of what appeared to be three teams of shoppers, who, by the random assortment of wares in their carts, were not there to beef up their own wardrobes. What was left? One XL trench coat. One XL gold peplum top. One L short-sleeved tee. Over in the children’s department, I noticed that someone had squirreled away a cream-colored shirt in a medium. I felt a momentary impulse to snatch it up like a gold nugget in a stream before remembering that it wasn’t really my style.

It was a scene being replayed in Targets all over the country, where the line swiftly disappeared — only to reappear soon after on eBay. There are currently well over 11,000 Jason Wu for Target items up for auction – most promising “NWT” (new with tags) — and selling at considerable markup. A $39 poplin dress is going for $180. A purse that was $49 is selling for $280. Free enterprise in action.

Designer collaborations with low-priced chain stores – and the frenzies that accompany them — are nothing new, as those of us who still wake up screaming from the flashbacks of the Lagerfeld for H&M stampede back in 2004 will attest. And they will no doubt continue — though Target imposed limits on how many items customers could order online, it set no such restrictions on what went down in the stores. Company spokesman Joshua Thomas told the Wall Street Journal this week “the company was ‘disappointed’ there was so much hoarding.” EBay put it in more calculating terms, noting that “this week the marketplace … reflected the public’s enthusiasm.

It may be “disappointing” that a handful of eBay-savvy pros can change how an entire line of clothing is distributed to the masses. But just because a designer goes down-market at the same place you buy your economy-size bags of cat litter, it doesn’t make the world of fashion any more inherently fair or democratic. If it were, designers wouldn’t be creating clothes with size 0 teenagers in mind. It’s just how it is. And so I left Target Sunday morning with dishwashing liquid but no new dresses. I didn’t mind. I’ve got my sights on spring’s new Marni for H&M line anyway.

You’re probably curious about a few things right now. One, is this idiot serious? I am. Two, what do I look like shirtless? Very cold. And, perhaps, three: How did this happen? How did a regular guy stumble into a job of emaciated youths and anonymous six-packs? How does one become a “model” for Ambercrombie & Fitch? One recent Tuesday afternoon, I was walking down upper Broadway trying to ignore the rain and avoid eye contact with every other street-bound soul when it happened. I was discovered. Yes, discovered.

“Hey! Hey!” a curly-haired 20-something I soon learned was named Vanessa shouted after me. “Hey. We just love your look.”

“Excuse me?” I said.

“We just love your look. What are you doing later? Would you be interested in modeling work for Abercrombie & Fitch? Full-time, part-time. Whatever’s best. I’m a recruiter. And we just love your look.”

Now, this came as a rather large surprise considering a) I’ve been walking down streets for 26 years and this has never happened before and, b) I exclusively wear items purchased at either JC Penny or Kohl’s and am rarely (never) described as fashionable.

“I am downright flattered,” I told Vanessa, and meant it. What I knew about modeling was limited, but I was under the assumption the work likely entailed both more sex and more money than my normal reality as a journalist. (Which involves little, and less.) I told her I was in, so Vanessa jotted down my contact info and disappeared into the rain, promising to call.

To my surprise, two days later, she did. But by then I wasn’t so sure about the whole deal. I mean, Abercrombie & Fitch? I had never even been inside one of their stores, I explained to Vanessa. Would I also need to advertise clothing by not wearing any? Must I pout? What would my fishing buddies back home in Wisconsin think?

Vanessa, cool and persuasive, got me to agree to come “check out” a “group interview” at the original Abercrombie & Fitch store along the South Seaport a few days later. If nothing else, I figured it would give me something to write about. Vanessa added: “They’re going to just love you.”

When I arrived I didn’t know what to think. But after I was inside the store, that stopped being important. Everything, actually, except Abercrombie’s pulsing ephemera stopped being important. If you’ve never been to Abercrombie, let me tell you, it definitely kills one’s ability to form coherent, logical thought. No one has ever discussed matters of philosophy or the status of Iran’s nuclear capabilities within its confines. Everything’s dark and loud and confusing. You half feel like you’re playing laser tag and half like you’ve bumbled onto a reshooting of “Eyes Wide Shut.” The cultural aesthetic of the store straddles all of these notions. It’s a confounding, bombastic and erotic slice of our American zeitgeist. Put another way: White people love it.

Which, some accusations have gone, is exactly what’s wrong with Abercrombie — and its hiring policies. In 2003, several Asian, black and Hispanic job applicants filed a discrimination complaint in San Francisco against the company, alleging they were steered into the stockroom, not the sales floor. They said the company didn’t hire minorities as models. The clothing conglomerate denied this and defended their hiring policies as protecting their trademark look. The suit was eventually settled out of court for $40 million. (Company spokespeople declined to comment for this article.)

At the group interview, I learned that being a model at Abercrombie requires more than gyrating and shimmying, though these are necessary skills. Models are also called upon to fidget with clothing. Additionally they must memorize and employ as many as 10 company “taglines” to greet and dismiss customers, including: “Hey! What’s up?” “Thanks, guys! Catch you later!” And “Hey! What’s going on?” — not to be confused with “Hey, guys! What’s going on?”

As the job interview wound to a finish, I had a rare, existential moment. Maybe I was doing something wrong and deceptive here. All the other applicants really wanted this modeling job. They grinned. They chortled. They wisely advertised themselves with the words, “outgoing,” “positive” and “energetic” after the manager informed us they “wanted an outgoing, positive and energetic workforce.” Was I taking a job from someone in a desperate time — just to write an article?

One earnest applicant even told me he “hoped I would get it. You said some interesting things.” Really? I thought, convinced I had actually blown my cover when I described myself as “dogged and inquisitive” rather than positive. But the exact opposite occurred: I was hired, and told to be back at the store for orientation at 9 a.m. the following Sunday. My pay would be $9 an hour.

I’m sure many things of worth occur at this time of the week, like “Meet the Press” or, for some people, church. For me, however, 9 a.m. Sunday has little to no consequence. I never schedule anything of import early Sunday morning because I’ll likely be either late or still drunk. Luckily, Abercrombie isn’t something of import.

So that Sunday, I arrived for orientation 35 minutes late, half-hammered from the night before, and unapologetic. Something crazy then followed: No one — and I mean no one — cared. Not the other employees, assistant supervisors, or the manager. It was wild. There I was, unshowered, on one hour sleep, and barreling toward a traumatic hangover, and all anyone said was, “Hey! What’s up? What pants size are you?”

I now understand why pets got it so good. Nothing is ever expected of them. They just have to be friendly and be adorable.

I chatted up any coworker who would talk with me. To make conversation, I informed several people that Abercrombie had sold Ernest Hemingway the shotgun he’d used to kill himself in 1961. I also told my associates in jest that my favorite movie was “Zoolander.” I got a lot puzzled looks during those hours of orientation, so I decided to keep quiet and work on my taglines.

Even then, my manager told me I still wasn’t “ready for the show.” This was related to the fact my pants weren’t tight enough. Weren’t tight enough by far. At Abercrombie, I cannot overstate the cultural impact of wearing very skinny jeans, then plunging a thumb into each front pocket. This stance is very important. If you haven’t tried it before, I suggest you do.

With taglines memorized and skinny pants hugging things rarely hugged, I was ready for my first day at Abercrombie. I was ready to be a part-time model.

After enduring one last hiccup for wearing the wrong color of Chuck Taylor shoes — “are those bright green?” — I was put on greeting duty at the front door. This was my moment. I was Abercrombie & Fitch.

When a Korean family stepped inside, I fished out my most potent tagline immediately: “Hey, guys! What’s going on?” They looked at me strangely, didn’t reply, and darted past. This happens a lot when tourists “are taglined,” my co-greeter, another Vanessa, told me. Us models hurl the most American of colloquialisms at thousands of foreign-born tourists who have rarely encountered such Americana before. In that case, I said, what’s the point of taglines? She paused for a moment and said she didn’t know. I agreed.

What I learned about being a model? It’s crushingly boring. I’m sure it’s different for Giselle or Tyra Banks, who get to adopt languid poses on some beach in Australia. But this was New York. And I was wearing skinny jeans and lima bean Chuck Taylors.

Two hours into a six-hour shift I quit. I tried not to be too melodramatic about it but was tempted to hand back my red-and-blue plaid shirt like I would a gun and badge to a police chief, telling my bosses I did everything I could to save those kids on that burning bus.

No one seemed too upset to lose me. Lady Gaga was pounding. The air was thick with perfume. Beautiful people were smiling everywhere. As I walked out, my manager glanced at me, grinned a wide one, and said: “Thanks, bro! Catch you later!”