Bob Dylan had a very unique sense of fashion and his influence still shows in clothing today. Dylan popularized skinny jeans, skinny blazers, and Cuban boots as well as flyaway hair. Bob Dylan had two unique styles in the 60's: folksinger Bob (in his early days) and electrified Dylan (mid 60's). Learn to dress like Bob Dylan here.
For an early Bob Dylan, wear straight legged blue jeans. For the electric Dylan phase, be sure to wear black skinny trousers or black skinny jeans.
Be relaxed with your shirt. The early Bob Dylan often wore a striped flannel/camp shirt with a cloth jacket over it to give it a very Woody Guthrie-esque touch. In the mid 60's, Bob Dylan would wear a button up shirt (usually in white or a dark color) with a skinny blazer over top. Sometimes, for example his appearance at the 1965 Newport Folk Festival, he would wear a leather jacket over the shirt.
Wear work boots in brown or black for the early phase of Dylan and Cuban heeled boots for the mid 60's phase.
Find the right sunglasses. In the mid 60's, Bob Dylan was rarely ever seen without his infamous Ray Ban Wayfarer sunglasses. While real Ray Bans can be pricey, there are many Ray Ban lookalikes that will work.
If your hair is already curly, just grow it out some. If your hair isn't, take a photo of Dylan to your hair stylist and tell them you'd like your hair like his. Women: if you have wavy or curly hair, try not brushing it for a while to see if it divides itself into soft but messy pieces. Women with short but curly hair might want to get a perm, while women with straight hair might want to get it curled. Slightly frizzy is best.
Watch the stunning Bob Dylan documentary "No Direction Home".
Women will want to avoid wearing makeup, as Bob Dylan was very natural and never tried to hide his physical features. Be who you are and be beautiful!
Listen to Dylan as much as possible. Blonde on Blonde and The Freewheelin' Bob Dylan are two great places to get started.