Miles, Chet, Ralph & Charlie: An oral history of The Andover Shop

Interview with Constantine Valhouli, author of Miles, Chet, Ralph & Charlie: An oral history of The Andover Shop

Miles, Chet, Ralph & Charlie: An oral history of The Andover Shop chronicles how The Andover Shop, an iconic clothier in in Harvard Square, became an unexpected literary and jazz salon in the 1950s. At its center stood its renowned proprietor, Charlie Davidson, whom The Boston Globe eulogized as “the Baron of Bespoke” after his death in 2019. Constantine Valhouli, whose lifelong admiration for and friendship with Charlie began when he was only 10, has compiled a fascinating oral history of the man and the legend. The was recently chosen by the Robb Report as one of “27 Style Books Every Man Should Own, Read, and Learn From.”

ML: Please tell us a bit about yourself and your background.

Whenever anyone asks that question, the first thing to come to mind is Dr. Evil’s response in the Austin Powers movie (“My childhood was quite typical. Summers in Rangoon, luge lessons…”).

Brooks School, Georgetown University, Columbia Business School. Worked at the Washington Post in the later years of the legendary Ben Bradlee, and for the former White House press secretary Ron Nessen. Writing was my first love, even if I became professionally distracted from it for some time.

ML: What inspired you to write Miles, Chet, Ralph & Charlie?

One of my favorite plays is A.J. Gurney’s “Love Letters,” and part of the attraction for me is that the production requires only two actors, a couch, an end table, and a bottle of wine. The Andover Shop under Charlie Davidson felt a lot like that. An unexpected literary salon in a tiny clothing store with just one chair. But in that chair, you might find Miles Davis, Chet Baker, Alec Wilder (who literally wrote the great American songbook), or Albert Murray (one of the greatest overlooked public intellectuals of the twentieth century, who also advised on Jazz at Lincoln Center).

As I got to know Charlie over the years, I came to see a fascinating overlap of style, jazz, and social issues. Charlie understood the power of style and clothing to make someone seen. And he used that power to help raise the profile of people whose talent he admired.

ML: Like Miles Davis?

A perfect example. Charlie was pivotal in the shift in Miles’ look from the “big band” outfits with the padded shoulders to the understated, Ivy League style. Part of this was that Charlie felt that Miles’ spare new sound required an equally understated look. But part of this was also outrage that Miles –– who he felt was a genius –– was forced to walk in the “colored” entrance to venues and hotels because of segregation.

Charlie did that for others, too. Helping people navigate the complex social codes of Boston, New York City, and Washington.

ML: For the readers who don’t know The Andover Shop, could you explain briefly why the store and Charlie are so significant?

Traditional American menswear began with Brooks Brothers in the 1800s, but J. Press took things in a new direction at the turn of the last century. And alumni of J. Press went on to found some of the most influential shops that reflected the specific lenses and interests of their founders. J. Press is closely aligned with Yale and Princeton, and the Andover Shop is associated with the New England boarding schools and Harvard. And Charlie loved jazz and literature, so his shop brought together consummate insiders with complete outsiders.

ML: Why did you choose to tell the story as an oral history?

One of my favorite writers, and someone with whom I was fortunate to collaborate, was Nelson W. Aldrich Jr., an early editor of The Paris Review. His oral history of George Plimpton, George Being George, is just wonderful, and it was told from the perspective of the people Nelson interviewed. Each of the people with whom I had spoken was such a wonderful storyteller that I did not want to impose my authorial voice over theirs. I wanted to foreground them, let them tell their stories in their own words. Nelson suggested doing it as an oral history. That was the moment of narrative alchemy, when the stack of notes became the beginning of a book.

ML: The main voices in the book –– Bruce Boyer, Alan Flusser, and Richard Press –– are three of the living legends of traditional menswear.

I feel so incredibly fortunate that they (and so many others) were so generous with their time and stories. And insights. What was particularly wonderful was there was a dialogue among them, and they did not always agree on things. The oral history format turned out to be a perfect way to hold up these differing perspective and let the readers decide. (Thank you, Nelson.)

A reader came up to me at a recent book event and said, “I’m not sure if this is a book about style with a history book hidden between the lines, or a history book with a bonus book on style.” That delighted me.

ML: So, which is it?

Both. And also, a character sketch of someone who was simultaneously very generous and supportive but also incredibly ornery and complicated. Somehow, all of the elements combined into something which resonated with so many different audiences. I’ve been stunned by the reception it’s received. Robb Report recently included it in a round-up of “27 Style Books Every Man Should Read”; it was nicely reviewed in the Boston Globe and mentioned favorably in the New York Times. And it was for a time, #1 on the Kindle charts in the Jazz, Jazz Biographies, and Fashion categories.

ML: The book seems to have taken on a life of its own?

I really wasn’t expecting any of this. Especially since the book was self-published. We weren’t able to interest any publishers or even agents in it. These days, they don’t seem particularly interested in mass-market books that don’t have elves and vampires and werewolves getting all romantic.

ML: Which clothing items from The Andover Shop would you consider to be the most iconic?

Without doubt, patchwork tweed –– whether it’s jackets, waistcoats, trousers, or a scarf. There’s a scene in the book where Charlie explains, “It goes with nothing, so it goes with everything.” But Bruce Boyer recently pointed out that this is not an ironclad rule. If it is worn incautiously, it looks like you’re heading out for the Shire.

ML: What is the one clothing item that every customer of The Andover Shop must own?

Charlie wanted everyone to come out of the shop looking more like themselves, not like him. So, all those items in the store were like a painter’s palette for him. Or like that wand shop from Harry Potter. He wouldn’t sell the same wand to everyone.

ML: Are “ivy style” and “preppy style” the same? If not, how do they differ?

This question merits a full interview of its own. Perhaps we should do a roundtable with Bruce Boyer and Richard Press? But off the top of my head, there were three periods of the style: when it was a private look of the northeast colleges from 1900 through the Second World War. After the war, the G.I. Bill made college more accessible, and the look became nationally known as “Ivy style.” And I think “preppy” started in the 1970s or 1980s –– the same relationship that rococo had to baroque. A little de trop. What I find fascinating is how these shifts reflected differences in how the country saw itself –– where did it look for style guidance, what did it aspire to be, and how did these change over time.