Phil Sears Schoonmaker wears a black knit tie 98 percent of the time. This one preference serves as a symbol for his entire approach to dressing.

Thirty-seven-year-old Schoonmaker, a New York-based business process consultant, is a living embodiment of the idea that less is more, of restrained taste and bold simplicity. With his superb balancing of the hip and traditional, he’s a testament to the timeless appeal of the Ivy League Look.

In addition to knit ties, Schoonmaker digs suits with narrow lapels, old and puckered oxford shirts, engine-turned belt buckles, canvas sneakers, selvedge denim, and vintage Timex watches. (J. Crew, who’ve been using real people in their catalogs lately, should grab this guy as their next top model.)

Ivy-Style recently spoke with Schoonmaker about his perfectly simple and simply perfect style.

IS: Describe your business attire. What kinds of suits, shirts, ties and shoes do you wear?

PSS: My style is guided by simplicity. I wear suits and sportcoats cut in the traditional Ivy League manner and prefer fabrics that are more casual in nature. I seek out vintage Chipp and Brooks Brothers exclusively, and purchase my custom-made items from Paul Winston. His passion, creativity and attention to detail are a rare find.

My shirts are cut slim with a button-down or tab collar and a flap pocket. I purchase all my shirts from Mr. Tom Davis and the made-to-measure program at the Madison Avenue Brooks Brothers. Mr. Davis has been with Brooks Brothers for more than 40 years. He is a consummate gentleman and one of the best dressed men I have ever met.

I wear a black silk knit tie 98 percent of the time. When I’m not wearing a black silk knit, I wear one of my vintage unlined Brooks Brothers rep ties. My preferred shoe is Alden’s longwing model in either color eight shell cordovan or brown suede. I also wear Alden’s unlined suede chukkas, especially for travel. (Continue)

Was John F. Kennedy the most Ivy of US presidents, or did the most important man in the country actually encourage American men not to follow the Ivy League Look?

That depends on whether you’re talking about President Kennedy the nation’s leader, or Jack Kennedy relaxing among friends and family in Hyannis Port.

On assignment for the latest issue of The Rake, I examined the split between Kennedy’s public and private life, and how this was reflected in his wardrobe.

The text of the article is below, or you can download a printable PDF.

Setting the President: John F. Kennedy’s dress sense was central to his public persona, forming no small part of this truly modern president’s enduring iconography
By Christian Chensvold
The Rake, Issue 7

Photographs of John F. Kennedy generally fall into two categories. In the first, we see him at his family’s Cape Cod retreat, sleeves rolled up, wearing khakis grass-stained from touch football, or clad in Nantucket Reds and sunglasses sailing the sea. In the second, his presidential kit, we see another man altogether. Kennedy’s dark suits hang with a certain awkwardness, the shoulders large and high, his two chest buttons both fastened.

Though both are equally iconic, these two images of JFK reveal the sartorial differences between the man’s public and private lives. Privately he was the Choate and Harvard-educated scion of a patrician American dynasty, while publicly he was a progressive young Democrat, commander on the frontlines of the Cold War, and careful crafter of a public image in the new age of television.

This schism makes JFK both the ultimate preppy president — his administration reigned at the height of the Ivy League Look — and an ironic hastener of the look’s decline, undermining the very style he so perfectly embodied. Though Kennedy could hide neither his Catholic faith nor brahmin accent, this first great image crafter of the TV age could strengthen his broad appeal with two sartorial gestures: He would wear two-button suits instead of three-button sack models, and he would eschew buttondown collars. The result, noted LIFE Magazine in 1961, was that the president’s clothes “fail to conform to current Ivy League fashion.”

Before becoming a style setter, Kennedy started out as a ragamuffin. “As a young man he was notorious for his personal disorder,” writes Neil Steinberg in “Hatless Jack: The President, the Fedora, and the History of American Style.” “His boarding-school roommates complained of his messiness, particularly with clothes. He would show up with his shirt untucked, or without socks, or wearing a rag of a necktie.”

Before his marriage to Jacqueline Bouvier in 1953, “Kennedy had been a sloppy dresser who favored baggy suits, clashing shirts and ties, and ratty tennis shoes,” according to historian Thurston Clarke.

With Jackie’s guidance, Kennedy’s style evolved into a paragon of simplicity and understatement. His casual weekend mufti was collegiate and Northeastern — Shetland crewnecks, penny loafers sans socks, white t-shirts, polo shirts and chinos, with a notable absence of pattern. His suits were solids or light stripes, shirts almost always white with a short straight collar, his ties discrete reps and clubs. Like Steve McQueen, another charismatic public figure with subdued taste, Kennedy gave his clothes style, rather than the other way around, a testament to the idea that clothes should never upstage their wearer.

Sartorial simplicity suited Kennedy best because he had star quality, an air of innate dignity, recalled his physician Janet Travell, “that was the product of personal reserve, self-respect, style and a distaste for ostentation.” But there was something else. With his sunglasses and convertibles, ironic wit and military heroics, Kennedy had something no American leader had ever had before: cool.

Much of Kennedy’s cool came from his hair, a Samson’s mane of potent charisma and something Kennedy famously avoided covering with headwear. “In a hat he looked far older and almost unrecognizably ugly,” writes Steinberg. “And he knew it.”

Kennedy’s effect on American taste was palpable. “Kennedy sets the style, taste and temper of Washington,” wrote GQ in 1961. “Cigar sales have soared (Jack smokes them). Hat sales have fallen (Jack does not wear them). Dark suits, well shined shoes, avoid button down shirts (Jack says they are out of style).”

As GQ points out, Kennedy set styles as much for what he negated as for what he advocated, and he stood in favor of two-button suits as much as he stood against buttondown collars. Historians have suggested that Kennedy preferred two-button suits because they better accommodated his back brace. Paul Winston, however, who made suits for Kennedy while working at his family’s legendary clothing company Chipp, recalls Kennedy wearing a brace during fittings at New York’s Carlyle Hotel, but says the button stance would not have mattered.

What is more likely is that Kennedy felt that while he couldn’t hide his privileged background in a television age that required mainstream appeal, he could at least obviate his image sartorially by wearing suits less redolent of the Eastern Elite and more becoming a man in the limelight of international affairs. When asked if suits for the newly elected president would be two-button, tailor Sam Harris said, “Certainly, two button. We don’t follow Ivy League or beatniks. We make gentlemen’s clothes.”

And when it came to shirt collars, Kennedy mocked his brother Robert in the press, telling LIFE, “He’s still wearing button-down shirts; they went out at least three years ago,” and told friend and confidant Paul Fay that his button-down collars were “too Ivy League.”

Privately preppy, publicly the leader of the free world, Kennedy was always an icon. But in the annals of sartorial history, JFK is less an example of a well dressed man than a man with tremendous charisma, and for such men understatement is always the best frame.

“Kennedy was a handsome and important man,” remembers Paul Winston. “That old saying that clothes makes the man? Not really. I think the man makes the clothing.”

Images from Time magazine’s “JFK Style.”

Young men who came of age during the heyday of the Ivy League Look could largely rely on their peers for sartorial guidance.

By the ’80s, things were much different, and the budding man of style had to rely increasingly on books, magazines and movies.

But today’s young men, who’ve never known life without the Internet, are positioned to be more precociously informed about clothes and style than any generation before.

Case in point: New Orleans high school student Robert I. Brown.

I discovered Brown’s blog while performing a Google Image search for Clark’s Desert Boots (turns out they’re his favorite shoe). At the top of his home page is a shot of Brown wearing a madras jacket, white oxford-cloth buttondown, glasses, and sporting a trim haircut. He looks simultaneously early ’60s and yet timeless and modern. Another shot shows Brown in a necktie and Fair Isle sweater vest.

As I browsed his blog, I discovered the tastes of a man much older: Fred Astaire and Cary Grant films, James Bond, exotic sports cars, The Rat Pack, “Mad Men,” and books on gentlemanly style and deportment are just a few of Brown’s interests.

And as if being a teenager and running a style blog weren’t impressive enough, naming it after himself — Robert I. Brown Style — is both an admirable assertion of impetuous youth and a bold stroke of confidence considering the number of bloggers three times Brown’s age who insist on being pusillanimously anonymous.

We began corresponding, and that’s when Brown really blew me away. No juvenile IM-speak in his missives: Brown’s correspondence, like his blog posts, is pithy and direct with a mastery of punctuation. My grandfather used to say, parenthetically, that you can tell a lot about a man from his punctuation. I’ve no doubt in his senior yearbook Brown will be voted “Most Likely To Become Editor of GQ.”

Brown describes his style as “simple elegance and preppy,” adding, “I like to wear Ivy garments because they make me feel a part of this tradition and legacy that will never go out of style. It’s timeless. Even though I’m only 16 years, I’m a bit of an old soul.”

You’ll hear more from Brown in his own words in an upcoming post. — CC

Thanks to Valetmag.com for picking up this post.

Yesterday The New York Times ran a profile on Manhattan District Attorney elect Cyrus Vance, Jr. that makes a passing reference to Brooks Brothers and Chipp. In Ivy-Style’s interview with Chipp’s Paul Winston, Vance Senior, who served as Secretary of State in the Carter administration, was mentioned as a frequent customer.

Though Winston recalls making clothes for Vance Junior as well, he hasn’t seen the new Gotham DA in nearly 30 years, Winston told Ivy-Style today. As for Vance the elder, “He was really one of the finest gentlemen who ever walked into our place.” Winston has shared some recollections of Vance’s cordial manners on his blog. (Continue)

One of the saddest phrases in the English language is “You missed a great party.” Well here’s one we all missed.

In 1957 jazz historian and Harvard/Yale alum Marshall Stearns threw the ultimate jazz-Ivy shindig. Held in honor of sitar player Ravi Shankar, the party juxtaposed Indian music with jazz, and included a jam session with Dizzy Gillespie. LIFE Magazine captured the soirée, which drew the kind of crowd only possible in New York: a dazzling melange of socialites and hipsters, artists and businessmen, with everyone dressed to the nines. Though LIFE only devoted one page to the event in the magazine, the LIFE archives include an extensive photo set entitled “East-West Jam Session.” (Continue)

When Timothy Thompson, an 18-year-old from Ashland, Oregon, was chosen by LIFE Magazine to have his first semester at Yale chronicled, a massive challenge lay before him. Not only did he have to adapt to the school academically and socially, he had to do so while a reporter and photographer followed him around campus, capturing each awkward moment, for nine weeks.

Thompson was the subject of our previous post, in which we dug up his lengthy profile in the January 8, 1965 issue of LIFE. A reader later left a comment showing what became of Thompson after college, then another reader found his obituary (Thompson died in 2004 at age 58).

In the obituary I noticed that his sister, Ardith Da Costa, lives in Petaluma, California, 40 miles north of San Francisco and the next city over from me. I telephoned her, and Mrs. Da Costa was happy to talk to me about her brother and how the LIFE feature came about.

IS: How was your brother chosen by LIFE?

ADC: There were 250-500 Yale prospects LIFE was considering. They whittled it down to five pretty quickly, and the reporter Donald Jackson seemed to have a good rapport with Tim. That was probably the final determination.

IS: How did Tim get into Yale?

ADC: He was salutatorian in his class and was accepted to Yale, Penn State and another East Coast school. He had the marks and was well rounded, having been active in sports and band. And he got an academic scholarship, since there was no way we could afford it; he came from a pretty simple lifestyle and there were four kids.

IS: When he came home for Christmas, what did he tell you about his first semester?

ADC: One of the vivid experiences he shared was about him coming from a public school and immersing with East Coast kids from prep schools, who had had a whole different experience both academically and socially.

IS: After the story came out, did Tim become the big man on campus?

ADC: In the big picture, with the number of academically gifted kids there, when it came out he probably fleetingly stood out for 24 hours.

IS: The story is called “Freshman Blues,” and it certainly shows Tim’s struggles. It also makes the reader cheer for him to succeed. Was he pleased with how it came out?

ADC: Yes, he felt they portrayed his experience accurately.

IS: Tell us about his military service.

ADC: Tim was in ROTC, and he was drafted his senior year to serve in the Vietnam War. Because he knew Latin and French, the Army had a special assignment for him, and he worked in Army Intelligence. He never spoke about what he did while serving.

IS: How would you characterize Tim as a person?

ADC: He was definitely warm and caring. If someone needed something, he’d be there in a heartbeat. He had a good sense of humor, and was very determined. And he was very outgoing and well liked. His freshman roommates became lifelong friends. He gave a lot back to Yale, and yet as much as he liked living on the East Coast he still had his friends from where we grew up. He managed to keep his connections diverse, and really valued his contacts, family and friends from all his different stages of life.

— CHRISTIAN CHENSVOLD

On newsstands now is one of those book-like magazines LIFE puts out when someone important dies — in this case, Edward Kennedy. “The Kennedys: End of a Dynasty” provides plenty of photos and family history for those who don’t want to wade through a full biography. I especially liked this photo of JFK from 1946. — CC

Bruce Boyer herein presents his first piece for Ivy-Style, an interview with Bill Thomas of Bill’s Khakis.

Khakis and jeans are the iconic American work pants, both having been around for over a century but coming into global status after World War II. The democratizing effect of these trousers — everyone from top CEOs and celebrities to road workers has at least a pair of each —  cannot be overestimated. Every clothing designer on the planet has these trousers as essential components of their creativity. Ralph Lauren is fond of wearing his jeans with a dinner jacket, while both Dolce and Gabbana wear wear their chinos black, low slung, and razor cut.

For U.S. soldiers returning from World War II, khakis were the all-purpose trouser. With the huge de-mobbing of soldiers after the war, coupled with the GI Bill for higher education, these durable tan cotton trousers became an essential part of the casual campus wardrobe. If a student had a pair or two of khakis, a Shetland sweater, a tweed jacket or blazer, and a few oxford-cloth buttondowns, he was pretty well set.

In the tie-dyed, flower-power 1960s and ’70s, the versatile tan trousers were largely replaced by patched and decorated denim. But khakis never disappeared, and started to make something of a resurgence in the ’80s, along with faint stirrings of a returned interest in Ivy League style. One can conveniently date this movement from the publication of The Official Preppy Handbook in 1980.

By this time Ralph Lauren had already been mining what he realized was a heavy lode promoting his Old WASP Look, with growing success, for 12 years. His Anglo-American Old Money Look included a substantial closet full of 1950s college staples, coupled with Savile Row and Oxford University classics. It was getting harder and harder to find The Real Thing in U.S. stores —  Brooks Brothers had capitulated, and campus clothing stores across the country were being converted to pizza shops — and Ralph knew it. In the face of one crazy trend after another, Lauren had the courage, sense and sensibility to stick to tradition. He copied the authentic Levis (jeans, shirts, and ranch jackets) because the Levi Strauss Co. had gone off making bell-bottomed cotton pants in sludge-toned colors. He also made buttondowns without polyester, and pastel-colored crewnecks. By the mid-’80s Polo was raking it in.

About this time a young college student named Bill Thomas discovered a pair of World War II khaki pants in an Army-Navy surplus store. I now turn the story over to him:

As a kid, I’d describe myself as the biggest kid who could still play sports. I was used to getting clothes in the “Husky” department. So I was also used to always feeling slightly restricted in my clothes. People who are just a little heavy will know that feeling, of clothes being just a little tight, perhaps a little inhibiting.

Anyway, one day I went with a few friends to an Army-Navy surplus store, and I tried on a pair of original World War II khaki pants, which you could still find in those days. It was something of an epiphany. The pants were actually comfortable, I couldn’t believe it. They were full in the leg and seat and crotch, the rise was high enough, and they were well made. I don’t want to make too much of this, but I felt somehow freer, more relaxed. I was able to move and not feel constricted, the trousers weren’t pulling at me. It was a revelation, and I was hooked on these old khakis. (Continue)

Playboy in its early years has always struck me as the ultimate men’s magazine. The emphasis on jazz and literature gave it a highbrow edge not found in today’s magazines, in which articles on socially relevant topics, rather than aesthetic matters, provide the weight and seriousness.

Moreover, Playboy’s editorial vision really did encapsulate a lifestyle, whereas today a “lifestyle” magazine is not one guided by philosophy, but by consumer choices. Of course, Playboy is in fact largely credited with creating the modern urban male consumer.

Like bohemian writers in tweed jackets or jazz musicians playing avant-garde music in gray suits, Hefner wore conservative clothing while radically changing America’s views on sex. Recently I discovered a tattered paperback called “Big Bunny,” written by Joe Goldberg in 1967. The book chronicles Hefner and his empire and includes the following passages:

Black-haired, instense, slightly under six feet, he looks, in his often-photographed costume of white button-down shirt, orange cardigan sweater, slacks, loafers and pipe, like a college senior on his way to class.

And later:

[Hefner's] dress is conservative-casual. His suits are custom-made Continental or Ivy League — he has two complete wardrobes. But he says, “Taste isn’t something you’re born with, it’s something you develop. When I came out of the war, I was wearing the broad shoulders, wide lapels like everybody else. But when I went to work [as a copywriter] for Carson’s [a Chicago department store], I discovered Ivy and Brooks Brothers and wore it consistently thereafter.”

That is, until he started wearing pajamas all the time.

Lastly, let this be a lesson to our younger readers: There was a time when it was possible to wear conservative clothes unironically, keep your hair neat and smoke a pipe, and still be a Casanova. — CC

Photo from the Chicago Tribune.

John Vliet Lindsay, mayor of New York from 1966 to 1973, personified the resolute confusion with which clubby, liberal WASPs faced the social upheaval of the era.

Entering politics as a successful young lawyer, Lindsay represented the wealthy Upper East Side of Manhattan, known as the Silk Stocking District, in Congress from 1958 to 1965. While serving, he compiled a liberal voting record on matters that would have little immediate impact on the residents of his wealthy district.

This abstract approach to politics, which had little to do with serving the immediate needs of his constituents, brought Lindsay attention and admiration as a Congressman. It would fail him, however, when he moved into the mayor’s office. (Continue)