One of my go-to sources for the Yankee look, Ivy Style, has a fantastic Q&A with one of ACL’s heroes Mr. G. Bruce Boyer. Some of my favorite quotes below.

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

Bruce Boyer: 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.

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 born to it in the ’70s 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 it.

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.

Get comfortable and read the entire interview here.