When Sight & Sound magazine invited the great American filmmaker Whit Stillman to vote in its once-a-decade poll for the greatest films of all time, among the ten films he chose was an obscure Alfred Hitchcock movie titled “Young and Innocent.” Released in 1937, the film starred British teenager Nova Pilbeam as a fetching, fearless young woman who offers a helping hand to a man wrongly fingered in a murder. This nifty confection may lack the psychological complexity of Vertigo or the sheer terror of Psycho, but for Stillman, who is 71 years old, it has a certain resonance.

“As one gets older — at least as I get older — I really appreciate innocence and freshness,” Stillman told me when I called him recently in Boca Raton, Fla., where he spends some of his time when not in his home base in Paris. “There’s not a lot of wokeism here, I have to say,” is his assessment of his current city. He seems to enjoy its remoteness from the circles in which he usually travels. “I know absolutely no one,” he says. “I know people up the coast. A lot of people of my ilk settle in Palm Beach and elsewhere, but because I never know my plans, I can escape all dinner parties.”

“Young and Innocent”: That title could have been used for nearly every one of Stillman’s five feature films to date. His “doomed bourgeoisie in love” trilogy, as he calls it — consisting of the modern classics Metropolitan (1990), Barcelona (1994), and The Last Days of Disco (1998) — chronicle, with equal parts good cheer and good humor, the romantic affairs and moral questions that exercise young WASPs. Nearly every major character in the trilogy is young, and most are profoundly innocent.

“You’re dealing with guilt and implication of guilt and escaping guilt, but it’s with this total innocence, really — I love that,” Stillman says of Young and Innocent, which replaced another, far-better-known Hitchcock film that had appeared on the list Stillman submitted to Sight & Sound a decade earlier, Strangers on a Train (1951). That film — centered on a tennis player (Farley Granger) whose plans to marry into a prominent political family are upended after he unintentionally becomes a party to a murder scheme — appealed to Stillman for his own particular reasons, too. “I grew up in Washington — you know, East Coast — and Strangers on a Train is really good about that,” he says. “One of the things that I love about Hitchcock is he’s so good at social milieu.”

But surely not better than Stillman, whose own background left him unusually well suited to make films about preppies. He was and is one. One of three children born to John Sterling Stillman — whose distinguished career included service in the Navy, a stint in JFK’s Department of Commerce, and lifelong devotion to the Democratic Party — and his wife Margaret, Whit checked all the boxes: He was dispatched to the toniest schools, invited to debutante parties, and graduated from Harvard. Plenty of Hollywood people sprang from similarly lofty backgrounds — Bette Davis went to Cushing Academy, Grace Kelly was a child of Main Line Philadelphia, Howard Hawks was the scion of a well-off midwestern family — but Stillman is unique in being entirely unapologetic about it. He objects to WASP writer Philip Barry, whose much-loved plays — Holiday, The Philadelphia Story — often portray people of his class as stuffed shirts. “He’s sort of more inside than I am, and he does this crowd-pleasing thing,” says Stillman, who admits that he once indulged in something similar: In Metropolitan, the Sally Fowler Rat Pack — the little platoon of debutantes and their escorts who chastely congregate and pontificate at after-parties — are meant to be likeable, so Stillman contrasted its members with the thoroughgoing scoundrel and sex maniac Rick Von Sloneker, who is distinguished from the debs and their beaus simply by being a titled, rather than untitled, aristocrat. “I don’t like derogatory stereotypes, but part of Metropolitan’s popularity is because it uses that too,” Stillman says. He knew he needed a well-heeled foil to make the well-heeled heroes and heroines appealing.

On the whole, Stillman’s films are conservative in the sense that he chooses to romanticize rather than renounce his milieu. In Metropolitan, debutante Audrey (Carolyn Farina) is a lovely, bookish girl who, against all odds, draws inner reserves of chivalry and spirit out of her sullen, initially party-pooping escort Tom (Edward Clements); in Barcelona, naval officer Fred (Chris Eigeman) and his businessman cousin Ted (Taylor Nichols) vehemently tout the benefits of NATO, capitalism, hamburgers, and the limbo to the anti-American-inclined locals in Spain; and in The Last Days of Disco, the assorted young professionals who occupy their nights in clubs spend their days toiling contentedly, if not always profitably, in such respectable occupations as advertising, book publishing, and the New York district attorney’s office under Robert Morgenthau.

Several centuries of drama have accustomed us to protagonists who chafe against their jobs, families, or society, but Stillman’s well-adjusted, well-off characters exist happily within their institutions. They embrace their inheritance with confident enthusiasm; they are devoted to their civilization’s more charming emblems — the practical detachable collars in Metropolitan, the trade-fair girls’ neato outfits in Barcelona, the degenerate but reformable fraternities in Stillman’s 2011 college comedy Damsels in Distress. This, the filmmaker says, is a legacy of his father: “An uncle of mine who was full of wisdom — a really wonderful man — would make observations about people, and he said, ‘You know, your father’s whole life is defined by loyalty to institutions.’ So, very loyal to the Navy, very loyal to Harvard, very loyal to the Democratic Party, very loyal to Cornwall-on-Hudson, New York, and the Black Rock Forest.”

Yet, as an adolescent, Stillman did not express quite the same comfort with his class heritage. Instead, he had something of the skepticism about traditional society later voiced by Tom in the early scenes in Metropolitan. Today, Stillman describes himself as a “social criminal” for dissuading his sister from having a debutante party. “My parents were just breaking up, and they had planned for her to have a big debutante party at our place in Cornwall-on-Hudson,” he says. “Meyer Davis, the Philadelphia society-orchestra leader, was booked. . . . My sister was sort of agonizing about it. I talked her out of having it because I was such a jerk 14-year-old.”

But then his mother began sending him to “starter dances,” and he became a regular at mixers at his boarding school, Millbrook, in the company of girls from Miss Porter’s. Debutante parties followed. He permitted himself to be charmed by the affairs, but by then the whole family had acquired a bad case of the late 1960s. A fair amount of cognitive dissonance followed. Stillman’s father had followed the Democratic Party in its leftward lurch, and his brother was considered a radical at Harvard. Whit himself remembers reading Michael Harrington while spending all this time in the company of debs. “I was wearing an SDS button under the lapel of my tuxedo,” he says. “I obviously was aware of the contradiction. It was my little radical chic thing.”

Stillman finally rid himself of his illusions, or delusions, during a summer in Cuernavaca, Mexico, where he had family. He discovered that preppiness, far from being the exclusive provenance of WASPs back home, was an aspirational state for the local inhabitants. “There would be these country farm girls coming into town from the outskirts, and they’d dress like the preppy Pine Manor girls,” he says. “They’d wear these pastel sweaters and gold-looking costume jewelry. . . . I was thinking, ‘If these farm girls came to Cambridge, they’d be attacked as bourgeois.’” For his part, Stillman found the farm girls’ eagerness to model themselves on America’s upper classes endearing. “It just showed that there was this great world of people getting along and not having these pointless resentments and hatreds, and that we’re all in the same continuum of wanting a productive and comfortable life.” No longer radical, he was still chic.

When he began making movies, Stillman did the impossible: He held on to his principles. Metropolitan mirrors its maker’s evolution on deb parties and other seemingly frivolous functions: from scoffer to booster. “I sort of collapsed it in a short period of time in the movie,” he says. Barcelona was intended as a conscious “paean to the Navy.” “The Navy wouldn’t support the script because the guy vetting projects for Navy support was a real Holy Roller, and the Lord’s name is mentioned in the script,” he says. “But I thought I was getting away with it, because I was writing it: ‘Jee-zus.’” Ever magnanimous, Stillman admits that he has a certain admiration for the Navy official who took a stand. “I detest bad language and profanity,” he says, “but I didn’t really consider that profanity.”

Stillman was reared in the Unitarian Church, but when the pastor turned out to be on vacation at the time of his planned christening, the task fell to a hastily summoned Congregational minister. His progressive-minded mother was horrified by what she considered the orthodox language of the ceremony, but his more high-church-oriented godfather, sociologist E. Digby Baltzell (Puritan Boston and Quaker Philadelphia), remembered being put off by its wishy-washiness. “It’s so funny, this sort of Rashomon of my christening,” Stillman says. In his films, he advocates a modest, mild, eminently charitable form of Christianity — epitomized in the scene in The Last Days of Disco when “Amazing Grace” is sung, unironically, over a montage of heroine Alice (Chloë Sevigny) soldiering on with life after having contracted sexually transmitted infections — that does not depend on intellectual heft.

“Religion is not terribly believable, and yet there are a lot of things that are important to us that aren’t really visual or quantifiable,” says Stillman, noting that movies themselves are an illusion: “When you’re in a movie theater watching a movie, in the old days of projection — I’m not sure how it works now — two-thirds of the time the screen is black, the screen has nothing on it. Only one-third of the time is there an image, and yet you watch all that and you enjoy the whole movie.” His dogma is simple. “We choose to watch the movie, we choose not to watch the black,” he says. His characters loudly preach the American way of life in Barcelona, but they have no fire and brimstone when it comes to God. In Damsels in Distress, co-ed Violet Wister (Greta Gerwig) gently cites the biblical rationale behind finding a mate: “The Lord said, ‘Be fruitful and multiply.’”

Metropolitan has been adopted by devotees of Christmas movies — Stillman says he has worked hard to get the movie categorized as such — and it earns its stripes on the basis of a lovely scene at Saint Thomas Church in Manhattan. There, on Christmas Eve, Audrey listens to “O Come, All Ye Faithful” and tears up a bit — perhaps a little out of joy at Christ’s birth and a lot out of sorrow over her seemingly failed relationship with Tom. Stillman remembers how the scene came to be shot at Saint Thomas. “I went to see the verger, and I think he wanted to be nice but say no, so he said, ‘Yes, you can shoot, but you can’t use any lights.’ I mentioned this to the cinematographer — maybe I was with the cinematographer — and his reaction was, ‘Okay, fine.’” Another Christmas miracle.

The maintenance of appearances matters a great deal to Stillman, who believes that the current era of slovenliness and vulgarity need not continue in perpetuity. “I mean, the late ’60s and particularly the early ’70s were really pretty horrible, and things got better,” he says. “One of the reasons I love disco so much was that things were so bleak socially before disco, and suddenly then people were going out and there were these really fancy clubs.” Finding good in our fallen world, Stillman says he still knows of churches where people dress up on Sundays, and he declines to denounce Brooks Brothers. “They still have the good boxer shorts.”

Stillman’s career has been frustratingly fitful as he has endeavored to get his movies made — through no choice of his own, 13 years elapsed between The Last Days of Disco and Damsels in Distress, and another five between Damsels and his majestically appealing Jane Austen adaptation Love and Friendship (2016) — but he cheerfully describes being an independent filmmaker as being akin to running a small business. He has loved the rituals and discipline of business ever since he had a job raising money for a foundation many years ago. “I started reading all these sales self-help things like Dale Carnegie and Bettger, How I Raised Myself from Failure to Success in Selling,” he says. “I read all these manuals, and I loved them.”

His films have sudden, dramatic slashes of violence — even in the genteel Metropolitan, Rick Von Sloneker punches high-minded rival Nick (Eigeman) — but his characters generally recover in short order. In Barcelona, Fred is the victim of anti-American terrorists, but the near-tragedy evolves into an occasion for reflection, prayer, teamwork, the mending of fences; his antagonistic cousin Ted and the trade-fair girls join forces to keep a vigil. “I actually put one rose-colored glass on top of the other,” he says.

Stillman is chatty in conversation. He can be cheerful in the manner of Violet, heroine of Damsels in Distress, who hopes to improve morale and body odor on campus through the distribution of soap bars. He is humble, not wishing in our discussion of the decline of traditional menswear to separate himself from those who dress like slobs and admitting that he often prefers comfortable khakis. He makes assertions confidently — “What is our purpose on the planet? It’s to glorify God, so that’s the rule,” he says, paraphrasing a line in Damsels in Distress — but also asks questions, either rhetorically or just to keep the talk flowing. “Have you seen All Quiet on the Western Front, the new version?” he asks as we discuss the grimness of many contemporary movies. “Do you know the movie Love Story?” he asks later on. “I guess it was Post who owned Mar-a-Lago, not Hutton,” he wonders aloud when talking about Palm Beach (and Preston Sturges’s comic masterpiece The Palm Beach Story, also on his Sight & Sound top ten). “Was there a relation between Hutton and Post? I don’t know.” At last — something about the upper class that our chief cinematic chronicler of it isn’t sure of.

Some might say Stillman is a Pollyanna, but that would be unfair in a way he never is: His optimism is not born of ignorance but was arrived at intentionally — a conscious choice to embrace the world that made him a bulwark against a world gone mad. When Fred in Barcelona endorses what he calls the “shining-city-on-the-hill stuff,” he is expressing not merely his patriotism but his belief in the idea of patriotism as preferable to the idea of anti-Americanism — healthier, more wholesome.

In real life, Stillman is aware of contemporary horrors — his Twitter feed is full of condemnations of Russia’s war against Ukraine — but his answer to those horrors is fidelity in the sort of institutions favored by his father: the might of the military, the grandeur of the Ivy League, the comforts of Cornwall-on-Hudson. “There was the Great Awakening,” he says, looking to the past to express hope about the future; “people changed their beliefs.” Perhaps the young and innocent people who populate his films will ride to the rescue — maybe literally so in his latest effort, a just-announced series titled “The Splendid Affinities” about young people who take it upon themselves to help preserve democracy in a made-up Baltic nation.

After that series, Stillman intends to get around to Dancing Mood, a long-planned film set among Jamaican churchgoers. “The whole thing is, I’m a really square, old-fashioned Christian, and these are square, old-fashioned Christians,” he says. He may no longer be young, but he remains innocent.