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 it's 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
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
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
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
"Of course," he adds with a raspy sigh, "the clothes are a little tight now."