Probably taken in 1960, this photograph shows Dylan dressed like Huck Finn in a work shirt and engineer's cap. His choice in clothing reflects his interest in Woody Guthrie and traditional American music, as well as the financial challenges of a young musician.

Another early photo showing Dylan in work shirt and engineer's cap. His second album sold well, and in 1963 Dylan's clothing was more well-tailored, though he still favored work shirts, boots, and jeans. 1964 brought increased fame, and Dylan's "aw, shucks" demeanor was replaced by a more guarded attitude, crisp white shirts, trousers, jackets, and sunglasses.

Looking folkie in a blue work shirt in 1962.

In the early 60s Dylan continued to dress in work shirts, jeans, and boots, as in this 1962 Manhattan photograph.

After his 1965 tour of London, Dylan appeared at the Newport Folk Festival in slim trousers, high-heeled Cuban boots, and a polka-dot duelling shirt. London's Carnaby Street was the ground zero of mod fashion, and the clothing in this picture was probably purchased there.

Dylan startled the Newport audiences with an electric performance as well as his wild clothing.

At an airport in Sweden, Dylan sports another polka dot shirt. He seems to like polka dots of all sizes.

Listening to the first press of Blonde On Blonde in polka dots.

A beautiful photo taken in Central Park shows Dylan wearing a soft belted trenchcoat and polished black boots.

Wearing a Triumph t-shirt over a wildly pattern shirt in this photo from the Highway 61 Revisited cover session.

At an Australian airport in 1966, Dylan wore the perpetual polka dots with striped trousers.

From 1966 to 1974, Dylan took a hiatus from touring. This 1967 photo from Nashville Skyline shows a relaxed, countrified Dylan.

Relaxing at home in Woodstock in 1969, a country gent in sandals and boater hat.