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.