THE JOURNAL

Mr John F Kennedy visiting Oak Ridge National Laboratory, Tennessee, US, 24 February 1959. Photograph by Galerie Bilderwelt/Getty Images
JFK and the other sartorial icons who best represent Massachusetts’ City of Champions .
Boston holds a special place within the pantheon of great American cities, and the men who have called it home have forged a style to match. Pugnacious yet refined, proudly blue-collar yet home to the world’s most elite educational institutions, Boston has produced working-class heroes and Brahmin statesman, beer-brewing revolutionaries and historian-quoting janitors. (Sure, that last one was fictional, but in many ways Will Hunting is the embodiment of his hometown.) To coincide with MR PORTER team visiting Boston this week, we fete the city’s most stylish figures, from an outspoken Celtic to the best-dressed president in US history.
Mr Bill Russell

Mr Bill Russell (right) with head coach Mr Tommy Heinsohn during a game at the Boston Garden in Boston, 1974. Photograph by Mr Dick Raphael/NBAE via Getty Images
From Mr Ted Williams to Mr Tom Brady, Boston has produced no shortage of athletes who dressed well both in and out of uniform. But few have captivated the city like Mr Russell, whose 11 championships with the Celtics remain an NBA record. Mr Russell was ahead of his time in more ways than one. His off-court penchant for casually elegant suits foreshadowed the fashion choices of today’s basketball stars, and his political outspokenness (along with that of his friend, Mr Muhammad Ali) paved the way for the activism of Messrs Colin Kaepernick, Steph Curry and LeBron James, among others.
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Mr Red Auerbach

Mr Red Auerbach (middle) at the Boston Garden in Boston, 1967. Photograph by Mr Dick Raphael/NBAE via Getty Images
Mr Russell’s coach and mentor was equally tenacious, if more outwardly joyous, favoring bold checked suits and, of course, his famous cigar, which he lit up after every victory. (This trademark inspired many Boston establishments to post “No Smoking” signs with an explicit exception for the beloved coach.) His modern attitude – his Celtics were the first NBA franchise to draft an African-American player – helped make his Boston teams of the 1950s and 1960s among the most successful of all-time.
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Mr Malcolm X

Mr Malcolm X. Photograph by Mr Michael Ochs Archives/Getty Images
Born in Omaha, raised in Detroit, and most commonly associated with New York City, Mr Malcolm Little spent 12 years in Boston, from 1940 to 1952. It proved to be a formative era, producing two of his best known signatures. First came his browline glasses, which he required after reading extensively during a stay in prison. And then there’s his name: prior to leaving the city for good, he adopted the iconic “X”.
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President John F Kennedy

Mr John F Kennedy at the Democratic National Convention, along with Messrs Milton Berle, George E Jessel and Frank Sinatra, 1960. Photograph by Mr Bernie Abramson/mptv.com
The pinnacle of Boston style. His sartorial signatures – from the Wayfarers and polo shirts he favoured when sailing to the broad American tailoring he wore in the White House – remain shorthand for what it means to be a well-dressed New Englander. It’s hard to overstate the impact Mr Kennedy had on American style. In many ways, the way men dress today begins here.
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The Cars

Mr Elliot Easton of The Cars during a recording session in Boston, March 1980. Photograph by Mr David Gahr/Getty Images
“I’m Shipping Up To Boston” might be the city’s unofficial anthem, and Mr Steven Tyler its best known rock star son, but The Cars are the most stylish musicians to come from Boston. (Mr Jonathan Richman runs a close second.) The New-Wave heroes embodied the city’s signature working-class elegance, going from campus-ready tweed suits to leather jackets and faded jeans with ease (and often in the same photo), looking like a group of MIT students who had just discovered The Ramones.