Miles Ago


This week I met with someone close to Charlie Davidson, the founder of The Andover Shop who died recently at the age of 93. While cleaning out his apartment, the person found some 15 printouts of my 2008 article for Ralph Lauren Magazine. And not stashed in the same place, but rather scattered all about in his ever-expanding collection of bureaus. There were even email exchanges between us from about that time. It was the kind of charmingly eccentric anecdote one became accustomed to hearing about Charlie. 

The article in question was entitled “Ivy League Jazz,” and the subject matter so interested me that I launched a few months later. The piece was lost to the Internet lost for a time as there wasn’t a copy of it here. In 2015, with the help of some loyal readers, we pieced it together in this post, albeit not properly formatted. It’s now been laid out properly, and at the bottom you’ll find a little surprise. — CC

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Ivy League Jazz
By Christian Chensvold
Ralph Lauren Magazine, 2008

Sometime around 1954, jazz great Miles Davis walked into the Andover Shop, a small haberdashery in Cambridge, Massachusetts, and single-handedly turned the world of style upside down. Just as his groundbreaking album Milestones (celebrating its 50th anniversary next year) changed music, that afternoon in Cambridge shifted men’s fashion.

Miles emerged from the store clad head to toe in traditional “Ivy League”–style clothing, and in so doing merged two separate worlds—those of the establishment and the black jazz artist—as if fusing two dissonant notes to create a bold new harmony. The result was a crashing chord of cool that obliterated the line between square and hip, sounding a fashion fortissimo that lasted several years before fading into the silence of pop-culture obscurity.

Miles stocked up on tweed and madras jackets with a natural shoulder and narrow lapel; chino and flannel trousers; button-down shirts; knit and regimental striped ties; and Bass Weejun penny loafers. “It was a look that redefined cool,” writes Miles biographer John Szwed, “and shook those who thought they were in the know.”

“It sounds corny now,” recalls 82-year-old Charlie Davidson, who still runs the Andover Shop, “but Miles liked the real Ivy League look, and it became the hip way of dressing.”

At the 1955 Newport Jazz Festival, Miles went onstage in a seersucker sack coat, rounded club-collar shirt, and bow tie. Candid photos from this period reveal his taste for tweed sport coats and oxford-cloth button-down shirts that were so white, recalls jazz writer Rob Mariani, they “made you think you’d never seen a really white shirt before.”

Swing bands had their matching tuxedos; and bebop’s poster boy was Dizzy Gillespie, in his double-breasted pinstripes, Technicolor tie, and hipster beret. But the new sounds of the ’50s—hard bop and cool jazz—required a new look. Ivy League style fit perfectly, and its clean-cut understatement seemed only to further highlight the adventurous music of these jazz pioneers. “The old clothes looked drab to them, just as swing and traditional jazz did,” says Davidson. “The stage was set for something new, and it turned out to be my kind of Eastern, university, WASPy, old-line clothing.”

Soon Davidson was dressing such jazz luminaries as Stan Getz, Gerry Mulligan, Paul Desmond, J. J. Johnson, the Modern Jazz Quartet, and Chet Baker. “Musicians realized they looked better in that costume,” recalls jazz promoter Charles Bourgeois, who first took Miles to the Andover Shop. “It was a good look and still is. Next to a tuxedo or military uniform, there’s nothing that makes a guy look better than Ivy League.”

When Baker was booked at the Boston jazz club Storyville in 1954, says Bourgeois, “Chet arrived from California dressed like a ragamuffin with giant shoulder pads. I said, ‘You can’t be seen here like that.’” Just as he’d done with Miles, Bourgeois took Baker to the Andover Shop. And when the album Chet Baker in New York came out in 1958, it bore a cover photo showing the trumpet player looking the epitome of collegiate cool in a navy jacket, white button-down, and gold-and-navy rep tie, and with Brylcreemed hair.

A drummer for Charlie Parker and Sarah Vaughan, the legendary Roy Haynes—who’s still beating the skins today, at age 83—was another loyal Andover customer in the ’50s. He grew up in Boston, where, he says, he was surrounded by “natural shoulders, button-down shirts, rep ties—it was very popular at the time, and I was used to seeing guys from Harvard at jazz events.”

Decked out in their traditional-yet-hip Ivy gear, Haynes and Miles were named to best-dressed lists by GQ and Esquire, alongside elegant icons like Cary Grant and Fred Astaire, and blue bloods like A. J. Drexel Biddle Jr. and Dean Acheson.

The Ivy League look wasn’t only for those on the creative side of jazz. The cofounder of Atlantic Records, the perennially dapper Ahmet Ertegun—who helped shape the careers of John Coltrane, Charles Mingus, and Ornette Coleman—sought out suits at J. Press. And producer John Hammond, patron saint of jazz patrons, who was a Yalie and the grandson of Cornelius Vanderbilt, ambled around clubs dressed like a tweedy history professor while scouting cutting-edge talent.

As jazz evolved, embracing electric guitars and rock rhythms, the Eisenhower-Kennedy look gave way to tie-dye and denim. “Looking sharp was the standard until the late ’60s,” says Michael Cuscuna, who has produced reissues of Baker and Mulligan for his own Mosaic Records. “That’s when rock permeated into jazz and Art Blakey traded his silk suits for overalls.”

If the Ivy League style was cool in the ’50s, it only seems cooler in retrospect. Perhaps that’s because the look isn’t fleeting fashion but something timeless. The eight private colleges that are members of the Ivy League athletic conference may be for just a select few, but the clothes popularized on their campuses have been democratized into staples of classic American style. During the ’50s the unlikely pairing of African American artistry and WASP style not only created a new idiom of cool, but also helped set the stage for the civil rights marches and demands for equality that came a decade later.

Baker and Miles ultimately moved on to new sounds and new fashions, but Bourgeois has stuck to his sartorial roots. At 89 he continues to be director of public relations for the Festival Network, which operates the Newport Jazz Festival. “And I still wear the same clothes,” he says. “When you have something well made, it lasts a long time.

“Of course,” he adds with a raspy sigh, “the clothes are a little tight now.”

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And now for that little surprise. This stationery features The Andover Shop’s original logo, which was sketched by Charlie and a friend on a cocktail napkin at a bar in the late 1940s— presumably while listening to jazz. 

28 Comments on "Miles Ago"

  1. Very well written excerpt CC. Would like to have read your entire story.

  2. Christian | May 26, 2015 at 9:45 pm |

    Perhaps one of the whiz kids can use the Wayback Machine or something to find it. Coincidentally I went looking for it just recently and failed.

    Google cache? But don’t I need the exact URL?

  3. I’m guessing that living in New York means you purge old mags pretty often to save space. I find it surprising you don’t have a copy, but I suppose when you’re a writer keeping copies of all your published work gets old after a while…

    Perhaps the library, or the RL store; surely one of the tried and true employees has a personal archive of the publication.

  4. Great excerpt on a definite stylemaster from a definite wordsmith!

  5. For some of us, it’s the only way of dressing. Full stop.

  6. miles coverdale | May 27, 2015 at 6:15 am |

    And now, with the link provided by Etymologue, the full article via this link:

  7. Bags' Groove | May 27, 2015 at 9:23 am |

    Miles and other Ivy wearing jazzers hugely affected my get-up as a jazz obsessed kid in England. And a subscription to “Downbeat”, with it’s powerful images, was crucial in being able to see exactly what the coolest cats on the planet were wearing. A lifelong love of jazz and lifelong quest for the natural shoulder followed.

  8. Ward Wickers | May 27, 2015 at 10:14 am |

    I thought these sentences expressed something remarkable about Ivy style:

    “The eight private colleges that are members of the Ivy League athletic conference may be for just a select few, but the clothes popularized on their campuses have been democratized into staples of classic American style. During the ’50s the unlikely pairing of African American artistry and WASP style not only created a new idiom of cool, but also helped set the stage for the civil rights marches and demands for equality that came a decade later. ”

    Really well done.

  9. Christian | May 27, 2015 at 10:30 am |

    Thanks, “Miles Coverdale,” for putting together the pieces. The piece was written on the now defunct software program AppleWorks, and I never transferred it to another format, believing it would be on the web forever. But for some time now the URL to the story just took you to the home page for RL Mag.

    And thanks for the kind words.

    After so much research since that was written, what jumped out at me now was the timing: I think many are in consensus now that the heyday began in ’54, with a good cornerstone being the LIFE magazine “Ivy look heads across the US piece.” If Charlie’s memory is correct (note how the story opens “sometime around 1954…”), then Miles was perfectly on trend, jumping on board right at the beginning and then moving on a few years later once it started to become entrenched.

  10. G. Bruce Boyer | May 27, 2015 at 11:51 am |

    A great piece! The relationship between clothes and music is important to both subjects and should be explored more extensively and systematically. So many wonderful musicians, particularly jazz musicians, are also incredibly stylish dressers. Perhaps that should come as no surprise.

  11. Chris Riffle | May 27, 2015 at 11:53 am |

    I find this statement very interesting: “During the ’50s the unlikely pairing of African American artistry and WASP style … helped set the stage for the civil rights marches and demands for equality that came a decade later. ” Is anyone aware of scholarship on the commingling of jazz, WASP style, and the civil rights movement?

  12. Christian | May 27, 2015 at 11:54 am |


    Charlie once said “You’ve got to have great taste to play jazz.”

  13. Ward Wickers | May 27, 2015 at 1:49 pm |

    @ Chris Riffle

    I don’t know about Ivy style and civil rights, but there is lots written on jazz and the civil rights movement. Many whites listened to jazz during the era of Jim Crow and couldn’t square the two. They began to realize that the practice of racial segregation was an anathema to the values of this country.

    Growing up in the 60’s, I can remember seeing Louis Armstrong and Nate Cole on TV (Ed Sullivan Show, probably) and also seeing news footage of “Whites Only” bathrooms and signs displaying “No Negroes Allowed” on restaurant doors and wondering how could this be so. Perhaps wearing clothes that were normative (for whites at the time) and recognizable as conservative helped smooth the path, though that is only conjecture. Here are a few of links to articles on jazz and civil rights you might find interesting:

  14. @Chris Riffle You make an interesting point that doesn’t stray too far into politics but is at the heart of today’s discussion. The adoption of Ivy style by these artists was an effort at inclusion or assimilation. The recent controversy regarding the Duke professor reflects the same consideration. He argued that the use of common American fist names by Asians was an effort to assimilate into the dominant culture. The alternative is — for good or bad –to separate yourself from the culture by the adoption of visibly distinctive attire.

    Regardless of your opinion of the culture the effort is obviously positive. It’s a variation on the “think Yiddish, dress British” theme.

  15. @Wianno85 I will argue that the adoption of Ivy style by these musicians was appropriation. From bebop forward, jazz musicians were rejecting a way of performing for, and behaving around, whites and the dominant culture that they equated with minstrelsy. They weren’t looking to be “performing” and getting accepted on the dominant culture’s terms. Signifying with Ivy style was a method of one-upmanship on the status quo. Not only were they making cutting edge, highly intellectual, and risk-taking music that was ahead of anything else, but they took the white man’s clothes (who had his foot on their neck) and made them their own and wore them better. Miles Davis, Art Blakey, Lee Morgan, and on and on – I doubt that they needed validation from the racist status quo, and Miles Davis says as much in his autobiography. Miles Davis would knock you out for suggesting that he dressed that way because he wanted to assimilate and be included or accepted.

    Hip-hop style is a direct descendant of the appropriation of Ivy style by jazz musicians. Look at how ‘Lo Heads appropriate preppy and Ivy – do you think they want the approval of the Waspy set? ‘Lo Heads and Miles Davis et al took a style that was square and safe and made it look cool and cutting edge. Who has more style, Miles Davis or WFB jr? ‘Lo Heads or the KJP crew?

  16. So you’re asking who has more style, a jazz innovator or a political commentator? Hardly fair…

    As for Lo Heads v KJP…none of the above?

  17. No offence meant, but the Ivy League style somehow furthering the civil rights movement seems a little far fetched. What did these famous and talented jazz players wear prior to visiting the Andover Shop, bib overalls? I think not.

    It’s always interesting that these articles always use some city in the south as examples. We forget that Jim Crow existed in every state of the union in the 1950s. I would suggest that integration of the military in 1948 probably had an exponential effect compared to Ivy Style.

  18. MAC, that’s simply not true. Jim Crow—the state-enforced segregation of the races—was in the South and only in the South. There was customary segregation elsewhere, but we have customary segregation today.

    Maybe people prefer to live around people like themselves.

  19. Ward Wickers | May 28, 2015 at 12:09 pm |

    I can recall some of the old movies of the 1940s and 50s. Blacks were often portrayed in roles of servants and “Mammies,” wearing maid, cook, and butler clothing. When not in the servant role, they usually were seen as very poor, uneducated, incompetent and worse. Their clothes matched their roles. Same with whites playing ‘negro roles’ in black-face. Acquiring the Ivy-style look would have been a very dramatic change. It seems reasonable it would further the idea that blacks are people, too, change perceptions, and at least tacitly help advance the civil rights movement.

  20. Henry
    The only real difference was the state sanctions and the degree of prejudice. You might want to check out Jason Sokol’s book, “All Eyes are Upon Us: Race and Politics from Boston to Brooklyn”.

  21. Ward
    You might Google ” early jazz players images”, you’ll be hard pressed to find a jazz artist not in coat and tie.

    Both white and black actors and musicians performed blackface. Jolson did, even our fashion icon Fred Astaire did. I don’t get it either, but shit even bad art is still art.

    I can’t and won’t defend the portrayal of blacks as of low intellect. But, if you’re making a movie of wealthy or upper middle class or even middle class white Southerners prior to the mid 1960s the maids, cooks, butlers and even the mammies are going to be black. It’s how it was.

  22. Richard Maple | June 4, 2015 at 8:47 am |

    Esquire magazine’s first list of best-dressed men (September 1960) was written by George Frazier and was called The Art of Wearing Clothes. The list included Miles Davis. This is how he was presented.

    “MILES DAVIS—The thirty-four-year-old genius of “progressive jazz” trumpet is an individualist who favors skin-tight trousers, Italian-cut jackets. His seersucker coats, which have side vents, are custom made. His tailor: Emsley (New York), which charges $185 a suit.”

    Who was Emsley?

  23. whiskeydent | January 26, 2020 at 6:04 pm |

    Arriving four and a half years late, I’d point out that African-Americans of that era often dressed well as a way of receiving and/or demanding respect. So I suspect Mr. Davis chose Ivy precisely because it was the style of the white establishment. “I’m taking your clothes too,” might have been his message.

    Now take a look at the ads for Rowing Blazers and BoastUSA. Everything is new again.

  24. Rather cynical…

  25. Mr. Davis is on a constant rotation in my home along with Messrs. Monk, Coltrane, Tatum, Powell, and Garner. He had my respect before I even noticed the buttons on his collar – as one ought to do. His talent and art superseded his clothes and the body they covered.

    But having read up on Mr. Davis, articles from 2016 tell me that he always had a flare for style. And he grew up in what is considered an upper-middle class family – the son of a dental surgeon. Where his contemporaries chose more extreme looks, he chose his – not to combat “white establishment” – but to set himself apart from other jazz greats at the time. He looked to the influences of his youth for it.

    Thanks for reposting this article, Christian. I type this listening to Kind of Blue.

  26. Lottastyle | June 8, 2021 at 6:41 am |

    Maynard Ferguson brought ACTUAL style to jazz. Sartorial and audial. It’s passé to flog the same tired old names.

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