Over the past several decades, G. Bruce Boyer has distinguished himself as one of the most erudite writers ever to tackle the subject of menswear.

Born in 1941, he came of age at the Ivy League Look’s height in popularity. A graduate of Moravian, the fifth-oldest college in the US, Boyer went on to do graduate work at Lehigh University and taught literature for eight years at Moravian and DeSales University. He has lived most of his life in Bethlehem, Pennsylvania.

Boyer’s writing career began in 1973 with an article about the Duke of Windsor, penned shortly after the British royal’s death. Boyer submitted the story to Town & Country, and soon became the magazine’s men’s fashion writer. He has since written numerous books, most recently “Fred Astaire Style” and the forthcoming “Black Tie.”

Ivy-Style founder Christian Chensvold recently spoke with Boyer about the heyday of the Ivy League Look, its abrupt end, the sprezzatura of the WASP establishment, and why he doesn’t spend much time in online forums.

IS: You entered college in 1959. What were the typical items of clothing you wore at the time?

BB: A button-down shirt in the traditional colors: white, blue, pink, yellow or striped, a shetland crewneck, khakis and Weejuns. The other thing was argyle socks, and in the summer madras everything. For tailored clothing, the ideal would have been a navy single-breasted blazer, a Harris Tweed jacket, a gray flannel suit, and a tan poplin suit or seersucker. That was the standard stuff.

IS: Madras quickly leads us to what’s known as the Go-To-Hell look. How much of that do you remember?

BB: I remember that stuff from the early ’60s. I started to go to New York for shopping and my favorite store was Chipp. That’s where I saw the patch madras and tweed, even before Brooks. Because Chipp is gone now, people tend to forget them. But they were probably the most interesting and most important and the best of Ivy League clothing stores. They were always a little more expensive, too. If Brooks introduced the shetland to this country, it was Chipp that promoted the wild colors like coral, hot pink and lemon yellow. I think I had a cable-knit shetland in bright raspberry in the ’60s. Chipp also did all of the wonderful, wild tweeds: You’d get a tan herringbone with a lilac windowplane overplaid.

I also remember going to Langrock in Princeton, which was for me the greatest campus shop that ever existed. By the late ’60s, the whole town of Princeton was divided into two kinds of people: It was either tweedy professors or freaky kids. It was either guys in Harris Tweed suits, tortoiseshell glasses and bow ties, or kids in tie-dye and jeans. Yet everyone got along.

IS: The OCBD-shetland-khakis-Weejuns-argyles look is considered a uniform today, as apparently it was then. In hindsight we seem to have conflicting images of the style: On the one hand everyone wore the same basic things, but on the other hand, as you pointed out with Chipp, there was tremendous variety.

BB: I think the variety came not so much from the items within the genre, but from color. It depended on how out-there you wanted to be. On the one hand there was a big interest in drab colors. Olive green was a huge color. I remember having an olive tweed three-piece suit. A lot of guys wore olive or gray flannel and brightened it up with a rep tie, a pink button-down and argyles. But then there were more guys of a more dandyish bent who were really out-there with the lime-green shetlands and animal corduroy trousers in bright orange, and bright plaid sport jackets. You got a beat on a guy from his sense of color more than anything. Some guys were more quiet and conservative, and others were more out-there. Some guys looked more like bankers, and others like they spent their lives on the golf course, but they were wearing the same clothing.

IS: Did it feel like a uniform at the time?

BB: It certainly was a uniform, the way most traditional clothing is. What was maybe the most interesting aspect of it was the label: whose clothes it was that you were wearing. That’s what was prized more than anything. It was the label that had the prestige. There were certain labels considered to be more authentic than others, and that was the one you wanted.

IS: A lot of advertisements from the heyday talk about “genuine” or “authentic” Ivy League clothing. Tell us more about the importance of wearing the right brands.

BB: There were certain labels that rang true: Corbin trousers, London Fog raincoats, shirts by Gant and Sero. Tom Wolfe pointed out the difference in shirts between Brooks Brothers, J. Press and Chipp — one had no pocket, one had a pocket with a flap, one had no flap — and guys could tell that kind of stuff. They could tell a Gant shirt from a lesser brand. Weejuns, of course, were a top brand. Southwick was huge, probably the best-known suitmaker in any Ivy League shop. I think people think brand consciousness came only when designers started putting the label on the outside.

IS: What about the details associated with the Ivy League jacket? How trained were eyes for the details like the 3/2 roll, lapped seams and hooked vents?

BB: For guys who understood the look, those details were everything. You not only had to have those details, you had to buy it at a certain store. The store was probably more important than the brand.

IS: Then I suppose the answer is that you just went to the right store and then you didn’t have to worry about the details, because that’s what you’d get.

BB: Exactly, that’s why the store was more important than the brand. If you went to the right store, you didn’t have to know what a hooked vent was, you were going to get one. That’s how the store got its reputation. You didn’t have to know anything because they were going to take care of you.

IS: How did the small campus shops that carried private-label brands, and makers like Southwick and Norman Hilton, compare to Brooks and Press? Were they ahead or behind as far as styling went?

BB: Probably Brooks was the standard for shirts. If you had a Brooks button-down on, that was the real thing. You find that all over. George Frazier often told the story about being at a club in New York with John O’Hara, who was nuts about clothes. Frazier was taken over to meet O’Hara, and O’Hara looked at him and said, “You’re wearing a Brooks collar, you can sit with me.”

IS: And you’re saying he was being only half ironic?

BB: He wasn’t being ironic at all. What he was saying was, “You’re OK; sit down and have a drink.” It was the ticket in. O’Hara was typical of that certain Ivy League guy who would recognize a Brooks collar, and that applied to everything: Were you wearing the real penny loafers or not?

IS: During the heyday, there must have been peer pressure to get the collegiate look just right.

BB: I went to a more Eastern Establishment, conservative college, so if you wanted to be in a fraternity, which was one of the hallmarks of campus life, or if you were a jock on campus, there would have been enormous pressure for you to look Ivy League. The only guys who had any prestige who weren’t wearing Ivy League were a certain group of intellectuals who wore black turtlenecks and tried to look like Jean-Paul Sartre.

IS: At what point did the Ivy League Look go from being a young, modern, collegiate look to a reactionary, middle-aged look? When and how did this transition happen?

BB: There are a couple of things going on. You can’t point to one thing because things don’t fall in a straight line. But the look was originally Eastern Establishment Old Money, and that has held for a long time. If you go back to the turn of the century, those Old Money guys are wearing natural-shouldered clothing, basically what Brooks came to call its Sack Suit Number One.

IS: In contrast, say, to New Money financiers with shoulder pads?

BB: Yes, as opposed to what at the time would have been called traditional American clothing. What happened was that after World War II, because of the GI Bill — which was federal aid for higher education for GIs — a lot of guys started to go to school, and they did two things. First, they saw what the Old Money kids at Harvard and Yale were wearing and they imitated that, and secondly, they integrated their army wardrobes, so there was an awful lot of khaki around, to mesh in with the tweed. So that Old Money Look became popular, but that popularity was for a short time. I’d say from the death of FDR at the end of the War, to the inauguration of Nixon in ’69, the Old Money Eastern Establishment Ivy League Look became very popular because of the push for higher education.

But after 1969 you get so many other interests contending for the popular look: hippies, the British look to get ahead in the world, and Italian fashion. So you get these other groups chewing away at the popularity of Ivy League Style, though the Old Money guys held onto it. Then by the early ’70s the designer look in menswear had firmly taken hold, and that leads to the beginning of what I’d call Postmodern Preppy, where the clothing becomes a costume. A guy like William F. Buckley dressed that way because it was his heritage, but kids today dress that way because they want to assume a look of the moment. It’s not a real belief, it’s just a costume.

IS: But I think that has always been the case. For example, when I interviewed Charlie Davidson of the Andover Shop about dressing Miles Davis, he used the term “hip to my kinda clothes.” It wasn’t something you had to be born to in order to appreciate.

BB: What you’re talking about is the short period when it became popular. Yes, absolutely, we can credit this to Miles Davis and his ilk. In the ’50s the jazz guys started to put on Ivy League clothes because they were playing on campus, and they spread the word about Ivy League clothes to other campuses. Jazz helped spread the Ivy League Look, and the Ivy League Look helped spread jazz. Charlie Davidson put Miles in some clean threads, and he was converted like all of them were: The Modern Jazz Quartet, Gerry Mulligan — they were all wearing the Ivy League Look.

IS: What’s your take on the term “preppy”?

BB: Preppy is postmodern Ivy League. It’s a more conscious thing. Even the jazz guys who played on campuses very consciously copied that look and modified it. And Ralph Lauren made a fetish out of a lot of that stuff.

IS: Given that Ralph Lauren’s rise happened after the Ivy League Look had already fallen in popularity, do you think he saved it from extinction?

BB: If I were asked to put my money on it, I’d say probably yes. During the ’70s, you couldn’t get the kind of gear you would find in old campus shops unless you went to places like Cable Car Clothiers or The Andover Shop. That’s one of the reasons I would give Ralph a lot of credit, because he stuck to his guns when everybody else was changing. Ralph was the only who for years and years still used real Harris Tweed for sport jackets. He’s been better for menswear than anyone you can think of.

IS: The idea of authenticity that surrounds this style of clothing is inescapable, as it is a style popularized by the Eastern Elite. But I think it’s too facile to say that “preppy” is the later, self-conscious version of Ivy, and therefore less “authentic.” When Nelson W. Aldrich, Jr. uses the term “preppie” in his 1979 cover story for the Atlantic Monthly, he’s not talking about clothes; he’s talking about the WASP upper class, of which he is a member. So it depends on whether or not you’re using the term “preppy” pejoratively, in a post-1980 fashion sense.

It seems there are four categories of clothes-wearer: Ivy born to it, Ivy hip to it, preppy born to it, and preppy fashion follower. You can’t say a preppy guy from the ’70s who was born to it is inherently less “authentic” than a poor kid who went to college in the ’50s and got hip to it, just because the media or his peers refer to the former as a “preppy.” Preppy should not automatically mean ersatz, as it’s dependent upon how the speaker is using the term.

BB: I see what you mean, and let me add to that. When I wrote the Brooks Brothers article for Town & Country‘s May 1981 issue, I interviewed the president of Brooks Brothers, a man named Riley, and he said to me at one point, “Do me a favor, please don’t use the word ‘preppy’ when referring to Brooks Brothers.” I knew the word was much used at that time.

IS: “The Official Preppy Handbook” would have been on the best-seller list at the time.

BB: Right, and I said it was just a buzzword and I wasn’t planning on using it, and he said, “I just wanted you to know that I hate that word.”

IS: What did the word mean to him at the time, and why did he object to it?

BB: I think the term signified something ersatz, that everybody was doing it, and Brooks was above that. There’s something to it, and why I mention the story is that even now, as far as buying clothes is concerned, everybody is in nostalgia mode. A single way of dressing no longer dominates the market, as it did in other periods. And I think what designers are doing today is trying to recreate an atmosphere that goes with clothing. In other words, a person’s style today, especially among young people, no longer seems natural. There’s no longer any authenticity to it. Everything is in some way a costume.

IS: Does the notion of authenticity even matter anymore in 2009?

BB: There are certain people out there for whom it matters very much. At a website like The London Lounge, you read what those guys say about clothes, and right away you get the impression that if you don’t fold your pocket square a certain way, none of them will ever speak to you. If you don’t have your shoes made by John Lobb or Cleverley, you’re nothing. So it matters to those guys. But apart from that, fashion is what it is.

IS: We live in an inauthentic world.

BB: That’s exactly it. There’s a lot of style and no substance, and that’s what we’ve come to. The clothing doesn’t reflect what it used to.

IS: But isn’t one of the good things to come from this is that it’s created the possibility for a cult of taste? While the clothing doesn’t signify what it used to, it does tell you that someone made a conscious decision to wear something. If you’re a fan of J. Press, which is so comparatively small in the overall marketplace, and you see someone else in it, you know you have something in common. Not like the old days, when it may have said a lot about a guy, but at least now it says you share the same taste.

BB: That’s perfectly true. In a way, it’s like the rise of the dandies at the beginning of the 19th century. What you get is a group of guys who formed a loose club that was an aristocracy of taste. It was true then, and maybe ever since, that being born to the manner is not as important as having its taste.

IS: With Brummell, the taste was more important than the social station.

BB: And then the taste made the social station.

IS: The world of online menswear blogs and forums is recognized as a place of draconian cattiness. What’s your take on the Internet?

BB: It’s John Lobb London versus John Lobb Paris, and which one is better. That’s one reason why I don’t get involved. The other reason is that they’re amateurs, and I’m a professional, and I ought to get paid for my opinions.

IS: Contemporary articles refer to the Ivy League Look as being collegiate, as being primarily developed on college campuses.

BB: Yes.

IS: But some ads and articles from the heyday refer to Madison Avenue in conjunction with the Ivy League Look. Why is the term “The Ivy League Look” alternately used to describe campus dress — shetland sweaters, chinos and penny loafers — but also to describe the gray-flannel suit look?

BB: When Kennedy was elected in 1960, there were a lot of articles about what his cabinet members were wearing. Instead of wearing the dark suits that everyone else wore, they were showing up in tweed sport coats and poplin suits, and if I remember correctly, it was pointed out that Kennedy had brought over all these guys from Harvard. Look at Arthur Schlesinger, Jr.: You couldn’t find a more Ivy League guy, and I saw him in J. Press about eight months before he died. He was prototypical of the guy who went from campus to government. And I think the same thing happened with the guy who went from campus to Madison Avenue, or finance or law. He didn’t wear hard worsteds, he wore flannel suits and eventually got rid of lace-ups and started to wear Gucci or tassel loafers.

When George Bush senior became president, he complained that Castro called him a “fascist in a capitalist suit.” But it was an apt description. He has that Old Money Look and will wear boat shoes and checks with plaids in that kind of nonchalant way that says “screw you.”

IS: He was also told to tone down his look, which leads us to the present day: It seems there’s hardly anyone in the public eye — in politics, business or media — with the classic Brooks/Press look. Peter Jennings, Obama, Donald Trump — they all look the same.

BB: They’re all wearing Oxxford suits in the Midwestern grain-salesman model, a plain shirt and a “discrete” tie, but probably by Hermes. The only guy who’s ever mentioned for having the old prep-school, Andover/Ivy League Look is Tucker Carlson. I look at him and say it may be natural for him, but it doesn’t look natural. It looks like he’s trying too hard, but I can’t quite put my finger on why.

I think the reason nobody has that look is that they’re smoothing out their image to appeal to everybody. With Obama, you can’t pigeonhole him: He looks the same to people in Florida or Seattle. That’s what they want. The first guy to do that was Nixon, he had that demulsifying look where you couldn’t pin him down. He looked like he could have been a manager of something in Chicago.

IS: What about the idea of quintessential American good taste? Did The Ivy League Look achieve a kind of pinnacle of American style? What is the legacy of this style?

BB: Yes, it did produce an ideal that is still very appealing today. First off, America kind of invented the idea of sportswear, the idea that clothing could be comfortable but still have dignity. It used to be the Victorian idea that you could have dignity or comfort, but not both. Gradually Americans started to destroy that. That’s the great value of Astaire, because he could command your attention and respect while remaining supremely comfortable. This does come out of Ivy League clothing, and is accomplished in several ways. There’s the softness of it: The button-down shirt has a soft collar, the natural-shouldered jacket, wearing slip-ons with a suit. The Ivy League Look also did something I really love that I think is a wonderful way to think about clothing: They’d mix the formal and the casual, which is something the Italians have really learned from us. There’s a purposeful nonchalance, what the Italians call sprezzatura.

IS: I’m reading a novel set at Princeton in the late ’50s, and there’s a passage in which a boy is described as wearing his father’s 20-year-old Savile Row jacket, nipped at the waist, with a knit tie and blue canvas sneakers splattered with boat paint.

BB: Absolutely. There’s a memoir by Paul Watkins called “Stand Before Your God” about being an American at a British public school, and the guys who had the most prestige were the guys who wore their father’s old tweed jackets and 50-year-old Lobb shoes, which had a certain cachet that New Money just didn’t have.

IS: New Money doesn’t understand the appeal of old, worn family things.

BB: It’s the difference between a country house where none of the furniture matches; it’s just been collected over the past 500 years, and somebody else who comes into money by inventing the hula hoop and buys a whole suite of furniture for each room.

IS: What about the rumpled aspect of the Old Money Look? Aldrich is ultimately just one man’s opinion, but in his Atlantic Monthly story, he says the great secret about the WASP upper class is the tremendous effort and anxiety goes that goes into appearing nonchalant.

BB: Originally I think that nonchalance comes from a couple of different places. One certainly is quality. It’s better to have one good pair of shoes than a half dozen cheap ones, because the cheap ones look cheap even when they’re new, but the new ones look good even when they’re old. Quality by definition is the best you can get for your money. If you buy a pair of shoes for $500 and they last you 10 years, that’s $50 per year. If you buy a pair for $100 and they last you six months, which was the more expensive? I think the Old Money WASP guys were just cheap, so they always bought the best.

IS: Sure: Yankee frugality.

BB: Yes, that’s what I think it’s about. And the best always is the cheapest, if you have the money to buy it in the first place. The way we do it today is ask how much it costs. Nobody asks how much it costs over its lifetime — it’s just the initial price. And if you only look at the initial price, you’re going to get screwed every time. I think that’s what the Old Money guys thought, and I think they’re right.

IS: There’s one more piece to it, and that’s the inherent WASP abhorrence of ostentation, and so Brooks Brothers and other Ivy League clothes were always relatively affordable.

BB: The unofficial motto of Brooks Brothers was “Good clothes at a good price,” and that’s how they did it: They gave you good clothes at a decent price.

IS: Tell us more about the abrupt fall in popularity of the Ivy League Look. There must have been sudden and intense pressure not to look establishment or square.

BB: Once both Kennedys were assassinated, and the more the Vietnam War took hold, the more we turned away from the Ivy League as any kind of ideal. JFK’s cabinet was all guys from Harvard, Yale and Stanford, and yet it was thought, “They’re the guys who got us into all this trouble.” It was the war, I think. I really do. I tried to convince my students at the time that you could be in the New Left and still dress decently. But it was true that there was another pressure of uniformity to let your hair down or you weren’t taken seriously.

IS: Taliesin, one of our contributing writers, has written, “In the middle of Watergate, the establishment look — ‘three-piece Yale-gray suits, white shirts and club ties’ — started to become a liability, and wilder, newer styles came to be seen as evidence of credibility — or at least as the absence of taint.”

BB: In “Frost/Nixon” the David Frost character is wearing Gucci loafers, and later Nixon says, “Did you see him? He was wearing shoes without laces!” Somebody wrote at the time, when everybody switched from wing-tips, that “Washington was nothing but a town full of lawyers running around in Gucci loafers.”

IS: To look hip instead of square.

BB: Exactly. It showed that you had a more global sensibility, because these were Italian shoes. They meant that you were aware of the world outside of Newport.

IS: What do you still wear today from this genre?

BB: I have a photo from my mid-twenties in which I’m wearing corduroys and a button-down and a navy crewneck sweater, and that’s exactly what I’m wearing today, 40 years later. My jackets have a bit more shape to them because I go to a good tailor, but I dress pretty much the same. I’ve gone through different phases and trends and tried things, but I always keep coming back to a kind of Anglo-American look. I still enjoy wearing the Brooks cordovan loafers.

But what really pisses me off today is that it’s very difficult to get a true button-down constructed the way they used to be. It’s all fused collars now. It used to just be two pieces of cloth stitched together, and now there’s a lining inside that’s fused with glue. I get my shirts from Mercer because they still make the old-fashioned collar. It comes back from the laundry all wrinkled up, and people say, “Your collar’s all wrinkled,” and I say, “Yeah? Well they’re a lot more comfortable and I really don’t give a shit.”