On July 25, 1965, after a tour of London, Bob Dylan turned up at the Newport Folk Festival wearing a polka dot shirt, slim, fitted trousers, Cuban heeled boots with pointed toes, and a pair of dark sunglasses.  A strong summer wind gusted through the crowd.  When Dylan plugged in his electric guitar and launched into a blistering rendition of “Maggie’s Farm,” the folkies were scandalized by the entire scene.  Dylan had a whole new sound and a wardrobe to go with it.  The festival goers showered their icon with a hail of boo’s.  Many fans that had come to hear their Bobby Dylan strum an acoustic guitar and sing songs of freedom, could not reconcile this new, shocking version of their idol with the man they thought they knew.  After all, if he was a star, he was their star first – wasn’t he?


Raised in a middle class Jewish home in Hibbing, Minnesota, Robert Zimmerman attended the University of Minnesota where he began performing folk tunes at local coffee shops under the pseudonym Bob Dylan.  However, Minnesota was too small to contain him, and after his freshman year in 1961, he struck out for New York City to meet his idol, Woody Guthrie, who was dying of Huntington’s disease.  Not only did the young Dylan meet Guthrie, but he became what he would term “his greatest disciple.”  In New York, he quickly insinuated himself into the burgeoning Greenwich Village folk scene, began writing and performing.  For a time, he was a minor character with a small following.    

But before the year was out he had received a favorable review of his performance at Gerde’s Folk City on West 4th Street, and was signed to Columbia Records by A&R man John Hammond.  Dylan quickly went to work in the studio, and his debut, Bob Dylan, was released in March, 1962 – the same year he legally changed his name.  The album was comprised almost entirely of traditional folk and blues mainstays.  And although he could count Johnny Cash as a fan, his first album sold only a few thousand copies.   

However, Dylan did not sit idle.  He wrote at a furious pace, and by 1963 he had penned several of the best protest songs the world has ever heard.  One of these, “Blowin’ in the Wind,” appeared on his second album, The Freewheelin’ Bob Dylan.  Thanks in part to a successful pop rendition of the tune by Peter, Paul, and Mary, not to mention a well publicized romantic and professional relationship with folk singer Joan Baez, Dylan was launched into the greater public eye.  By 1964, having recorded another instant classic, “The Times they are a-Changin’”.   He had not only ascended to the top of the folk world, he had effectively established himself as the most important songwriter of the 1960’s.  And just as he had left his hometown, and later the small folk circuit attached to his university, it was not long before the scrawny golden son of the Greenwich Village folk scene found himself at odds with his erstwhile fans and their well-meaning yet rigid adherence to entrenched musical traditions.

Photographs taken during 1961-1963 show Dylan dressed like a folkie, wearing simple blue jeans and flannel work shirts, occasionally donning an engineer’s cap.  He was consciously cultivating a personal style.  And his persona during this time was Bob Dylan, folk musician.  But just as Dylan would not be constrained by any one style of music, his style of dress was destined to expand. 

It was, perhaps, his trip to the U.K. and London’s famed Carnaby Street (the epicenter of mod style) during 1965, where he played his last entirely acoustic set, that informed Dylan’s new rock and roll look, just as the brash electric sounds of British invasion groups like The Animals would resonate with his inner musical sensibilities.  This tour, captured by D.A. Pennebaker in his film Don’t Look Back (perhaps the first conceptual music video), also marked the end of his relationship with Joan Baez.  Upon returning to America, he moved into the Chelsea Hotel and began seeing fashion model Sara Lowndes.  Dylan was his own entity. And to the dismay of many, he had a trajectory all his own.  

By the time he hit the stage in Newport he had already released “Like a Rolling Stone,” a tune that, at approximately six minutes in length, defied the standard 3 minute verse- chorus-verse scenario that most songs abided by, shirked folk traditions with it’s tumbling organ sound, and showcased Dylan’s new direction as a deftly poetic songwriter with lyrics that seemed a thinly veiled, sharp tongued attack on the scene that had nurtured him.  The point is, Dylan had already found his new direction, lyrically, sonically, stylistically.  The folkies simply weren’t willing to accept it, or him.  Video footage of the festival captures one attendee saying, “Who needs him anymore? He’s part of your establishment…and forget him.”   

But Dylan would never really become a part of anyone’s establishment. Because his genius includes the ability to defy those who seek to label and contain him.  Just when you think you’ve got him figured out, he slithers into a new role, a new mask, frustrating everyone.  His 1965 album Highway 61 Revisited cemented his rock and roll transition and boasted unstoppable top ten hits such as “Positively 4th Street” and “Rainy Day Woman #5.”  1966 saw the release of the platinum double album Blonde on Blonde, the cover of which shows a blurred photograph of Dylan with wild hair, a scowl, and a checked black and white scarf.   

Dylan’s look during the mid-sixties was typified by stovepipe jeans and skinny trousers, polka dot shirts, fitted pea coats and soft-belted trenches, mod boots, scarves, and Wayfarer sunglasses.  And who could forget Dylan’s signature coif?  Part of the Dylan mystique was the unmistakable intellectualism.  He was a thinker, a poet, and while some would proclaim him a prophet, others called him Judas.  Nonetheless, the sixties belonged to Dylan.  He defined rock and roll and influenced the elite and the masses alike. 

Countercultural icon, literary giant, and hippy standard bearer Allen Ginsberg claims to have wept with joy the first time he heard Dylan.  John Lennon openly admitted that “Norwegian Wood” was Dylan style-inspired.  The scrawny Jew from Minnesota walked out on the Ed Sullivan Show, walked out on Joan Baez, introduced the Beatles to marijuana, had an affair with Warhol’s muse Edie Sedgwick (check out Edie Sedgwick, Style Icon) and wrote a song about it (“Leopard-Skin Pill-Box Hat” has been covered by artists like Hot Chip and Beck in recent years), and walked the strange fine line of being a countercultural figurehead intent upon blurring the lines between highbrow and lowbrow.  But was it all just an act? Was he really mystified by his own popularity?  The whole world was simultaneously rapt and confounded.     

Bear in mind, all of this happened in just a few short years.  For Dylan, life moved at a frenzied pace that even he struggled to keep up with.  After all, how does one live up to one’s own growing legend?  In July of 1966, he crashed his 500cc Triumph motorcycle near his home in Woodstock, NY (where he bought a home long before the famed hippy music happening seared the name Woodstock into the collective cultural landscape).  The accident marked the end of an era for Bob Dylan.  He quietly retreated into himself and prepared for his next incarnation.

To be continued…