A League Of His Own: The Andover Shop’s Charlie Davidson

A League Of His Own: His aloof demeanor may not be that of a man locked in the groove, but Charlie Davidson has spent seven decades making Ivy Leaguers and his very own jazz heroes “hip to my kinda clothes.”

By Christian Chensvold
From The Rake, issue 23 (click here for PDF)

Half a century ago, a certain social set really had its priorities in order. Life’s pursuits ran something like this: Jazz, tennis, newspapers, Yankees vs. Red Socks, Newport and Nantucket, sailing, contemporary literature, prize fights, prep schools and the Ivy League, cigarettes and cocktails, college football, Broadway shows, and New York parties that blended socialites with beatniks.

Somewhere in this cross between Old Money and the creative class, between college town and metropolis, between traditional and cool, lies what Charlie Davidson calls “my kinda clothes.” And what kind of threads are these? Multus ne multus, English country attire with an American twist and a guiding spirit of jazz-hip. This, after all, is the man who dressed Miles Davis in 1954 for the style chameleon’s Ivy League phase.

That midcentury date suggest Davidson is at the age when one is either long forgotten or a living legend. At 86, Charlie — as everyone knows him — is incomparably the latter, the last of a certain breed of American haberdasher from an age more golden than ours. He is the epitome of “old school,” and that old school, founded in 1661, is Harvard.

Since 1953 Charlie has operated The Andover Shop in Harvard Square, the off-campus commercial center of the distinguished university in Cambridge, Massachusetts. Along with his original and still-extant shop, founded in 1948 in nearby Andover (where it serves the elite Phillips Academy Andover prep school), Charlie has been dressing students and faculty in tweed jackets and penny loafers since before the Ivy League Look’s 1950s heyday. The entire Anglo-American look of chinos and buttondowns, herringbone jackets and Shetland sweaters, argyle socks and tassel loafers that Ralph Lauren sells around the world, Charlie Davidson has been selling since before it was popular the first time around.

“Charlie is the last of the greats of the natural-shoulder business, back when it was the power elite who were wearing that stuff,” says bespoke clothier and menswear historian Alan Flusser. “Charlie goes back when it was just for prep school and college students in the Northeast, and remains as the lone standard bearer of East Coast/elitist-trad male style. His eye for colors and materials is first-rate, and he is masterful in his interpretation of conservative New England style. He has been able to make a living selling his vision of classic American traditional style longer than any other retailer. This speaks to Charlie as much as a force of nature as well as a force of personality.”

The Andover Shop is certainly an unlikely style mecca. It’s not on Madison Avenue in the heart of Midtown Manhattan, but in a college town adjacent to the sartorially reserved city of Boston. The shop is tiny and merchandise is spare and presented without fuss. But the advanced sartorialist will immediately notice the copious bolts of fabric that line the wall, a dizzying variety of rare English cloth that Charlie has accumulated over the decades. The off-the-rack house cut is a two-button jacket with an undarted front, while bespoke services start at a modest $2,500, well within the limits of Yankee frugality.

But to stimulate Charlie’s enthusiasm — to get him to bust out the really rare stuff — one must demonstrate genuine interest in clothes and a certain esprit. With his well known aloofness, some shy customers feel like commissioning a suit from Charlie Davidson is like going to an audition. “He’s a brilliant designer and an excellent merchandiser, but a very private individual,” says Richard Press, grandson of the founder of rival Ivy League haberdasher J. Press. “I always felt that The Andover Shop was a very private commercial enterprise. It served a fairly narrow range of people who met Charlie’s very difficult credentials of acceptability. He didn’t seem to welcome customers he didn’t feel belonged at The Andover Shop. He’s a vastly entertaining individual, but does not suffer fools lightly. ”

In a 1995 article for Atlantic Monthly, John D. Spooner shares an anecdote about Charlie’s lackadaisical attitude when it comes to serving unknown customers. Seems one day a wealthy businessman came into The Andover Shop and ordered three suits. Charlie said him they would be ready in a month. “After five weeks,” writes Spooner, “the customer, whose last name was Zachary, called to inquire after his suits. ‘Not quite yet,’ Charlie said. Another two weeks went by and Zachary was put off again. Charlie had not made the suits. ‘He’ll get the message,’ Charlie told me. ‘I am not sure I like the cut of his jib.’ Four weeks more and Zachary called, irate. ‘What the hell do you do over there?’ he asked, ‘make the clothes alphabetically?’ After hearing this line Charlie made the suits. Zachary had passed the test.”

When it comes to style, Charlie reserves his greatest appreciation for everyday men with individual panache (what he and writer friend George Frazier would call duende, or a kind of magnetic charisma), not ambulatory mannequins dressed by designers — or tailors, for that matter. “The customer knows more about style and taste than the merchant,” he avows. What he notices most in a well dressed man is the whole picture, “from his haircut to his shoelaces,” which suggests something deeper, a core competence in the art of dressing and exquisite taste. Charlie scoffs at curriculum-based dressers punctiliously concerned with rules and genre perimeters. Sophisticated dressers, he says, see a wide horizon beyond buttondowns and striped ties. “Charlie has a larger sartorial vocabulary than the died-in-the-wool traditionalist,” says Paul Winston, whose family ran rival trad clothier Chipp. And while he’s the oldest practicing torch-bearer of the Ivy League Look, Charlie is strongly opposed to “looking like a ’50s caricature,” and cryptically calls Ivy style more of an attitude than a wardrobe. “You know a preppy,” he says drily, “as soon as he walks in.”

Charlie Davidson was the right man in the right place at the right time, he asserts, and the result has been a life so satisfying that he wouldn’t even consider retiring. “It’s a party all day long,” he says, “just being enthralled by the people who walk in the door.” Though his father had been a Texas farmer, Charlie grew up in Andover and attended the noted prep school. That he would eventually found a shop with strong ties to the school is rather magnanimous, considering he was kicked out (that’s right: the greatest preppy clothier was a prep-school dropout). After serving in World War II Charlie spent one semester at Bowdoin College in Maine, then worked for J. Press in New Haven, Connecticut, serving the Yale community. Whereas Brooks Brothers, which traveled frequently to prep schools and colleges, provided the upstanding establishment look, J. Press was more youthful, Charlie says, “adding a little more stylistically to get kids away from their father’s clothes.” During his brief stint with Press, Charlie sold a hat to Gregory Peck that the actor wore in the film “Gentlemen’s Agreement” (Peck doffs it in one scene, revealing the J. Press logo). Shortly thereafter Charlie opened The Andover Shop in 1948 at the age of 22.

“It was the perfect moment,” Charlie recalls. He hosted trunk shows at such leading prep schools at Groton, St. Mark’s and St. Paul where, because of his youth and cool attitude, he became better known than the traveling reps from the bigger stores. Five years later he opened the second shop in Harvard Square, where Charlie found himself at an outpost through which countless 20th-century luminaries would pass through on visits to the famed university. “Harvard Square is the epicenter of the universe,” he says. “The whole world goes right by and comes in here.” Former President George HW Bush was a former classmate and Andover Shop patron who inquired about Charlie all his life, and when African-American author Ralph Ellison received an honorary degree from Harvard, Charlie Davidson was his guest.

A jazz fan since he was a teenager, Charlie went on to befriend boyhood crushes such as Billie Holiday and Anita O’Day. And in the mid-‘50s, when campus concerts became popular and jazz musicians began taking style cues from their audience, Charlie provided clothing to such jazz greats as Chet Baker, Stan Getz, Paul Desmond, Gerry Mulligan and The Modern Jazz Quartet, and became lifelong friends of legendary producers (and Newport Jazz Festival founders) George Wein and Charles Bourgeois. Recalling a night with Charlie hearing Bobby Short at New York’s Carlyle Hotel, Rake contributing editor G. Bruce Boyer says the entertainer rushed over to give Charlie a hug, while the band waved at him as though he was their favorite uncle. “I share Charlie’s love of jazz,” Boyer says, “but envy him because he actually knew so many great artists, and they loved him.”

Adds Richard Press, “Charlie brought jazz musicians within the boundary of establishment style but still let them express themselves individually.” Charlie also became the chief clothing consultant — and closest friend — of George Frazier, Esquire’s witty style columnist and author of the seminal essay “The Art of Wearing Clothes,” who was said to have developed his own understated yet dapper style — chalk-striped flannel suit, pink oxford buttondown, navy dot tie and boutonniere — under Charlie’s tutelage. “Charlie is special,” notes Paul Winston, “in part for having outlived the very legends he’s dressed.”

Even as an octogenarian Charlie reamins “mad for clothes,” passing hand-me-downs to his tailor and acquiring new things with delight. “I love getting something new,” he says, “while my old clothes are like old friends.” Some things never change, including, apparently, the world around him. When you’ve turned your vocation into your own private gentleman’s club with yourself as grand pooh-bah, there’s something to be said for having rose-colored blinders on. “People say how much Harvard Square has changed,” says Charlie, “but I haven’t noticed. To me nothing’s changed. The ties get wider, than they get narrower — that’s it.”

Notoriously press shy, it took some convincing for Charlie to talk to The Rake, (though that was nothing compared to getting him to sit for the camera). His reasons for reticence are myriad, but they partly come down to the ephemeral nature of style, which is something you ultimately have to feel, not notate by chiseling into a block of marble. “I hate giving interviews because by next week I’ll change everything I said,” Charlie sighs. “That’s why I can’t read articles about me. I’ll say, ‘I said that?’”

Photos by Tasha Bleu.

27 Comments on "A League Of His Own: The Andover Shop’s Charlie Davidson"

  1. That Andover Shop place looks pretty Preppy to me, they obviously sell clothing other than blue and white OCBD, navy blazers and brown tweed jackets, khakis and charcoal pants, and God forbid, only navy ground ties and Weejuns. The place is obviously inspired by the Ivy anti-Christ Ralph Lauren, or visa versa. Chucker on gentlemen.

  2. Great profile Christian, thanks for the read.

  3. @MAC

    I think you hit the nail on the head when you said ‘or vice versa’.

  4. This is a man out of time. Time moves on, he doesn’t need to. Relevance is always to be had.

  5. Orgastic future | August 7, 2012 at 12:01 am |

    That tie selection is Awesome!

  6. Great post – I still remember the first time I walked into the shop….just a terrific place with wonderful history.

  7. Am I the only one that finds it odd that we are glorifying a man for his unwillingness to deliver on time? I think it might be another story if this had happened before the orders were purchased, but I think that passive-aggressive games do not make an icon.

  8. When I worked in an ivy shop, I never failed to deliver, but I did have my stash of cream, that I held back for specific customers or ones that would not debauch the item. I think most carriage trade salesmen do. One gets to know one’s clients’ taste very well and you know when they are ready to push the envelope. I often, actually made them buy an item, guarantying to buy it back if their wife or a girl at the office didn’t compliment them on it, never bought anything back. I taught a lot of men how to dress, like the men that taught me and the probably thousands of men Mr. Davidson taught. It would be interesting to hear from my fellow Ivy Style fans about those “Mr. Davidsons” in their early lives.

  9. I gladly offer words of honor and praise on behalf of anyone who’s succeeded at making a small business–especially a small enterprise that caters to particular tatstes such as this–work. The piles of folded cloth, the Scottish Shetlands, the spectrum of brightly shaded stripes and emblematics–all to the good. That The Andover Shop continues to thrive in this outlet-dominate, get-it-as-cheap-as-possible culture is reason to rejoice. Picky about cloth, quality cut-and-sew operations, and a certain atmosphere about the shop itself–again, all very good.

    The shop itself makes the case for a word other than “Ivy.” The house cut is a 2-button. Low button stance, wide(ish) lapel, longer length, and a point-to-point that no one would describe as narrow.

    Anglo American? American Traditional? Trad? Who knows. And probably not important, except that it transcends the boundaries of Ivy Heyday same ol’

  10. I think The Andover Shop still uses Southwick for MTM cut and sew. Maybe one of the few shops that has its own pattern (Andover model) on file at the Massachussetts factory. They’ll add a third button for those who insist on the tip-over 3-to-2.

  11. Craig Sevde | August 8, 2012 at 3:10 pm |

    I agree Good Read! If you were brought up shopping in stores like these with the trunk shows, etc. you enjoy it even more.

  12. @Matthew, I am not convinced money ever exchanged hands.

    As an FYI to our readers, Ivy Style writer Zach DeLuca works at the shop on Mon,Wed and Sat.

  13. Minimalist Trad | August 8, 2012 at 7:29 pm |

    The disappearance of the non-functional top button is not to be mourned; on the contrary, it is to be welcomed, even praised.
    It actually provides a far neater appearance, as does an unvented jacket. It may not be Orthodox Ivy, but it is certainly conforms to a gentlemanly tradition of avoiding attracting unnecessary attention to oneself.

  14. Sounds like a first class snob.

  15. I find it hard to believe charlie being described as “aloof”. charlie would be better described as a “wonderful, gentlemanly chameleon” and i mean that in the most reverential sense. I have been a customer of charlies (and larry’s) for 10 years. I have never left there without saying to myself that charlie is a “piece of work”. Interested in me and my take on the world and incredibly interesting, opinionated and entertaining in his own right.The man has met and dressed some of the greatest men in the past century and yet i think he would get along so well with the average joe sitting next to him at a Sox or Celtics game……..One other thing – it never feels like he , or larry trying to sell you anything. I relly appreciate Charlie and larry. I highly recomend them.

  16. I was on the phone with Charlie just the other day. He said there was construction going on and a room full of customers, and after considering calling me back, he still opted to go upstairs and indulge me on the phone for 40 minutes while I asked vague questions for an upcoming article.

    And yet when I made a kind overture to see if he’d like to provide clothes for our next photo shoot, something I thought would benefit his business, he politely declined. He won’t condescend to anything that might come across as self-promotional. All efforts to involve him in the MFIT exhibit have failed.

    Charlie’s Charlie, which is to say an original.

    BTW, does it feel like Zach is trying to sell you something?

  17. Michael Azarian | November 9, 2012 at 1:19 pm |

    I’ve known Charlie forever but have not had the opportunity to stop off in Cambridge (or Andover stores wher I grew up) more than a half a dozen times in the last 10 years. Aloof? No way! At least not to me.

  18. I may be mistaken, but Charlie’s reluctance to get involved may be due to the fact that the Andover Shop is far more traditional (conservative) (purist) (authentic) than BB and J.Press,and Charlie doesn’t want to be associated with “preppy” novelties in the guise of Ivy.

  19. My husband still wears/yearns for the Christmas Tree, wool slacks. They still fit! 1975

  20. Don "Kinder" Gordon '56 | April 27, 2013 at 10:43 am |

    Having spent three years at Andover (’52) I certainly remember the shop on Main Street, halfway between the school and the center of town. Charlie was always welcoming, and a comfortably effective salesman, not at all pushy, for which I was grateful.

    Thinking about all this today is a bit like revisiting another world…which it surely was.

    Thanks for the story!

    Don Gordon

  21. The Andover Shop is filled with rude snobs. I went to one of their out of town showings about eight years ago. These guys need a lesson in manners. I don’t know how the place stays open. I guess Bostonians are crude and vulgar elitist. To make matters worse, the showing that I went to was to help support Planned Parenthood. F.R. Tripler was a store for gentlemen and run by gentlemen. Salesmen who new the fine art of dressing and understated style. Not the peacock look of the Andover Shop and in latter years Paul Stuart. If I want the Andover look, all I have to do is go to the Polo shop in the nearest mall. Massed produced preppy clothes. The Andover shop like Polo is the GM of the natural shoulder set.

    John

  22. I started shopping at the Andover Shop in about 1975, after I’d decided to stay in Boston and buy real clothes. When I first started shopping there Charlie was aloof, all right, and the other sales clerks made me feel like I’d just wandered in from a farm. In a sense I had, because I’d been at Cornell in the sixties where the look was carpenter’s pants and L. L. Bean Farm coats. You can probably buy a coat like that there now, but back then no. The prices were low compared to the competition or designer shops. Charlie and I got to be friends when I discovered his interest in jazz, and he accepted me. Many years later he said he had seen me from the start as a “diamond in the rough.” You want the man’s approval because his taste is extraordinary, the cut and detail of the clothes they make is unmatched, simply cannot be found anywhere else. One example with do. He makes sportcoats out of all kinds of tweed without lapel welting or welted pockets; they are like suit coats but of heavier material. The lapels are stitched only at the outer edge, in other words, and they look almost cushioned. The luxury is there in the soft look, and the roll of his lapels can’t be found anywhere else. The tailoring is English-inflected with, more recently, some continental inflections. But there is nothing to compare these clothes to. Charlie picks out the fabrics, cuts the bespoke jackets and suits, and, as others here point out, is an endlessly charming conversationalist. I didn’t know his parents were from Texas. So are mine. That is the real reason we got to be friends, I think–he is not a snob.

  23. @droll

    I wouldn’t call Charlie a snob either. I’d say he really likes people. I’ve been there only twice (over the past three years).

    The first time I went in was by chance. I had stopped at J. Press, walked back to campus by way of Holyoke St., thought the window display was interesting, and went inside.

    I had never heard of Charlie Davidson, and he didn’t introduce himself. I wandered around, he mentioned my Alden loafers, pointed to his own, noted they were made nearby, and we got into a conversation. Fascinating man, full of life and good will. The next day, a Sunday, I had lunch with a friend at the Thai restaurant next store. While waiting for the friend outside, I checked out the Andover Shop window display again. Naturally, the store was closed. Who suddenly appears? The man from the day before. We exchanged greetings, and I asked him what he was doing there on a Sunday. He said a customer had bought some things, but had trouble getting around, so he was going to the bring the things to him. I said, “You’re a good man.” He wouldn’t have any of it. He said, “No I’m not, I just like what I do.”

    A year goes by, I’m back in Cambridge, and wouldn’t miss going to the Andover Shop again. I’m browsing again, the same man is there, and eventually he says, “Weren’t you here before?” I said, yeah, a year ago, etc. This time he introduced himself as Charlie Davidson, and in the course of our conversation, he gave me a lesson about shoes, which was a lesson about life.

    It went like this. I was getting pedantic about my cordovan loafers. I had begun reading up on the history of the clothes I had grown up wearing, and read that if you use a polish on cordovan that has silicon in it, it makes the color look too uniform, so I asked him about it. He said he never liked cordovan anyway because it faded, and when he had cordovan shoes he used to put black polish on them. Just like that. He said it in such a way that was pointed but friendly, not dismissive, and the conversation continued in another direction. Walking away, I reflected on what he said. I took him to be saying saying, “don’t take your shoes too seriously,” which could also be translated as “don’t take yourself too seriously.”

    So here is a guy who has a clothing store, is comfortably but impeccably dressed himself, but is very down-to-earth and keeps things in perspective. No bullshit anywhere near him.

    Then I googled “Charlie Davidson” and was not surprised to learn he was a legend.

    I would love to have something made there to my measurements, but I don’t live close enough to Boston.

  24. Robert H. Boyer | March 25, 2015 at 11:50 pm |

    Charlie Davidson is one of the world’s wonders, all knowing, marvelous conversationalist, and a great wit, I haven’t seen Charlie in person since maybe 1980, but when I feel I need a real lift, I get him on the phone, and when I finally hang up, I am absolutely exhilarated. Ceers to Charlie!

  25. Robert H. Boyer | March 25, 2015 at 11:51 pm |

    Oops. Cheers, not Ceers. Just thinking about Charlie gets me carried away.

  26. Robert H. Boyer | March 25, 2015 at 11:53 pm |

    Oops again. It’s Boyle, NOT Boyer, and I haven’t been drinking. Just shows what even thinking about Charlie can do to the mind.

  27. Al Shapero | April 14, 2015 at 6:34 pm |

    I became a customer in 1951-53 while a student at HBS. He taught me how to dress. I take issue with his being a remote deity. Along with dress clothes, I remember the British white wool submariners sweater and the hunting horn tie pin. When I graduated, my parents gave me $100 to buy luggage(to replace my service B4 bag. Charlie took time of to take me down to a mfr in lower Boston and helped to pick out two items. Unfortunately the only survivor is the tie pin.
    I’m delighted that he is still here(given his smoking early on, who knew).
    Blessings on you Charlie, you are the best!!!
    al

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