We Talked to Diana Vreeland’s Son Freck About Personal Style and His Life as a Spy

Welcome to State of the Suit , a new Robb Report series in which writer and menswear stylist Caroline Reilly examines the sartorial choices of candidates, pundits, and other movers and shakers. Whether it’s an ode to a departing president’s timeless style or a fantasy list of items we think would better suit a prominent figure, she has plenty of thoughts.

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Few men—few people in the world—enjoy the style pedigree of Freck Vreeland . At 97 years old, the son of the iconic Vogue editor Diana Vreeland has a litany of style rules, rituals, and regulations that he follows to the letter. The majority of them are so second nature to him he doesn’t even remark on them unprompted. Vreeland is unquestionably a dapper man. Impeccably tailored and effortlessly styled, he is an exemplary study in how to wear clothes that many a man would be wise to emulate.

But to simply dub Vreeland a style icon would be reductive: his career includes a life of service to the United States; as a secret CIA agent during the Cold War, a senior US diplomat under a number of presidents, and a US ambassador to Morocco. His mark on matters foreign and domestic is still felt today. Having seen the world—from a childhood spent watching Diana Vreeland primp for lavish evenings out, to rubbing shoulders with the most powerful men in the world—it’s Vreeland’s definition of a “gentleman” (an increasingly rarified, elusive concept) that reflects most comprehensively the profundity of his outlook, much to the delight of his twenty-one thousand Instagram followers who tune in for everything from his thoughts on the Middle East to tributes to his late mother.

Notably devoid of any mention of clothes, of dinner jackets or formal shoes, Vreeland’s qualifications for a gentleman are refreshingly simple, yet poignant: “To behave in a way that is thoughtful, without judgment. To have empathy and think of others. I hope that I am a gentleman,” says Vreeland via Zoom from the home he shares in Rome with his wife, Sandra Zwollo.

At once stately and disarming, Vreeland is sporting a classic plaid shirt, his gray hair neatly parted to the side. Zwollo, a picture of elegance with pillowy white hair clipped into a chin length bob and rouge-tinted lips, is the perfect complement. “I’ve never met anyone like Freck,” says Zwollo, attributing Vreeland’s life outlook at least in part to his mother. “And he abhors gossip,” she adds. Though Vreeland needn’t ever resort to something so petty given the wealth of fascinating stories he possesses.

At Zwollo’s urging, Vreeland is writing a memoir about his life, excerpts of which he generously shared with Robb Report . Whether it’s an account of his childhood in the colorful Vreeland household, to his years as a diplomat or his friendship with a young Jackie Bouvier and the Kennedys, the tales are riveting and filled with wisdom.

Vreeland’s Rules of Order

Of his style rules, Vreeland is a traditionalist but far from stodgy. His approach to dressing is rooted in the fundamentals of etiquette and respect, a philosophy of dressing that has fallen out of favor with far too many men. That means: a dark blazer at night for dinners; perfectly done hair; never short socks. “One should never show a piece of calf over a sock,” says Vreeland. His preference: gray.

One style lesson that Vreeland learned the hard way: shorts, only for the pool or beach.

“ Washington, DC, was built on a swamp, and it was for years listed by the British Foreign Service as a “tropical capital” where His or Her Majesty’s officials were expected to wear shorts in the summer. Air conditioning was as primitive as it was vital in tropical DC, and so one scorching day, inspired by my British colleagues, I came to work in shorts and knee socks. As I marched down the hallway to my cubicle and seated myself at my desk, I caught a few odd looks and chuckles from my colleagues. I didn’t care; I was cool and comfortable. A few minutes passed while I busied myself with various reports, and then I heard the door of the executive suite open and the heavy footsteps of Bronson Tweedy. The sound of his distinctive gait passed where I was sitting. His footsteps paused, and then returned. I could sense him standing behind me but he said not a word. It was about my shorts, I thought bleakly to myself. Feeling distinctly underdressed, I resolved to appear engrossed in my work in hopes he would go about his business. He waited; I pretended to ignore him. A stalemate.

Still without a word, he stalked back to his suite and shut the door. It was a clear statement that I should never even dream of wearing shorts again in the CIA, an implicit order that I obeyed. “

Vreeland’s Style DNA

Vreeland’s approach to style is unquestionably familial. Of his mother’s presence in that part of his life he says, “It set my life.” From his mother he learned to always wear a pocket square, from his father, whom he accompanied on many a trip to Savile Row , he learned to have his suits tailored in London so they fit perfectly . “My father was a New Yorker, but for clothing, it was only London,” says Vreeland. Both parents instilled the importance of perfectly polished shoes.

As a small child, I adored her. Photographs show me cuddled on her lap, or leaning against her, her arm protectively around me. In one picture, she stands like an elegant swan, with a chubby little boy, happily posing behind her. That was me in a nutshell: I never minded her telling me what to wear, or where to stand, or doing whatever she thought was best.

“ Dad’s ground-floor dressing room was similarly exotic to me, and I looked forward to occasionally watching him choose from an array of tailored suits, with the help of our butler Edwards—one in a line of many men, all called “Edwards,” no matter what their real name was. Edwards would carefully polish Dad’s shoes, using a dry shiny rhinoceros’ bone for the final touch. I was always particularly drawn to a pair of pointed yellow slippers. (In later life, I adopted with pleasure these North African babouche for informal wear around the house.) “

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Lessons in Restraint

Vreeland’s approach to style and shopping is marked with the quintessential restraint that seemingly all truly well dressed people abide by. He has brands, shops, and tailoring houses to whom he remains loyal. The fact that Vreeland is a man who likes structure and organization is a reflection of his upbringing and his career working for the CIA and as an ambassador. This need for structure though, does not inhibit his ability to embrace each moment. On the contrary, it allows him the security to truly do so. “He completely lives in the moment,” says Zwollo. “He doesn’t look ahead, and he doesn’t look behind it. It’s now.”

Vreeland is particularly fond of the brand Heron’s Ghyll , for which he’s recently modeled . “In London, I used to go to my tailor on Bond Street called Peacock; in Paris I usually went to Cerruti for a more modern Italian look, and ordered my shirts from Charvet on the Place Vendome. In Rome, it is Schostal for pajamas and socks .”

“If I give him his shirt and then give him a sweater over it that also has a collar – he says no, you cannot have two collars,” says Zwollo.

Living History

Vreeland sought to join the foreign service after graduating from Yale and a stint in the Navy; his father introduced him to Averell Harriman who told him that his aspirations of work in the foreign service would require months of training. “I said, ‘I need a salary immediately because I’m married – I need to start earning money.’ And he told me the only other option was the CIA, which was right down the hall. So I went there, and signed up.” Shortly after graduation he started working for the CIA and as a cover, was sent to Geneva in the Foreign Service.

A close confidant of the Kennedys, Vreeland supplied John F. Kennedy with the now famous phrase: “Ich Bin Ein Berliner” but it was in fact a young Jackie Bouvier who Vreeland met first. She and Betty, Vreeland’s then wife, were friends and classmates at Vassar. It was through Bouvier that Freck met John F. Kennedy, who was at the time Bouvier’s boyfriend. “Jackie always made sure that JFK looked good,” Sandra shares.

At our new home in Alexandria, Virginia, our first dinner guest was Betty’s Vassar friend Jackie Bouvier – who at that point had not even met her future husband, J ohn F. Kennedy . As Betty put the finishing touches on the meal, I set the table for three and surveyed our ground-floor apartment. Compared to my parents’ converted carriage house in Brewster, our apartment was small—just one bedroom and bathroom, a kitchen nook, and an L-shaped living and dining room. But it was Betty’s and my first home together, and it felt perfect to us.

“Jackie arrived right on time, her bulky camera still slung over her shoulder, fresh from her working day as an “inquiring photographer” for a local Washington newspaper. In public, Jackie was always a little reserved, even shy, but as we sat down to Betty’s home-cooked meal, she regaled us with stories of the people she had interviewed and photographed for the paper. The ever-gracious Jackie complimented us on how beautifully we’d fixed up our apartment. Betty and I were pleased; we were especially proud of the living room’s cushions and curtains of a matching blue-and-white cotton print—carnations with butterflies that we had chosen carefully at the best (but least expensive) New York outlet store. Jackie lifted her camera with its giant flash to photograph the two of us in our cheerful home, taking time to carefully frame us in front of our precious Henri Matisse–designed Mimosa wall tapestry, a recent wedding gift. I noticed her fingernails, which she usually kept hidden under ladylike gloves.

“We have something in common, Jackie,” I announced. “I also bite my nails.”

With one of her bright laughs, she replied, “Clearly the result of our overpowering mothers giving us anxiety complexes!”

I couldn’t question that conclusion, and so we drank to it. “

Of their iconic American style, Vreeland says the Kennedys were always well dressed. “Stable, nothing fancy or creative, but always elegant.” Sandra mentions how Jack Schlossberg is apparently quite a fan of Freck’s and we agree that Jack, like Freck, is also someone who knows never to reveal calf under his suit trousers.

Finally, Vreeland, Zwollo and I discuss the current election about which they are both incredibly optimistic—“stoked” to quote Vreeland directly. “I think [Kamala] is absolutely tops. I’m enthusiastic about the idea of having a female president and I think she’s the one. I’m all for it.”

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