Dressing as Bob Dylan is a great last-minute Halloween costume for any music lover. Dylan's retro style is easy to pull off with modern clothing. A harmonica holder and an acoustic guitar scream "Bob Dylan" before even getting to the actual outfit, especially when paired with some retro Ray-Ban-style shades and a newsboy cap. As for the actual clothing, start with a pair of denim jeans or black pants plus a leather jacket or blazer and a button-front shirt or a dark turtleneck for an extremely easy costume.
Bob Dylan’s basic style
Bob Dylan's sense of style over the years is part folk singer, part working man, part beatnik, generally with simple clothing easily found in your own closet or on the racks of any thrift store or department store.
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All of the clothing elements are not far off from something you might see classic country singers wearing, such as jeans and a leather belt. In his earliest songwriter days and beyond, Bob Dylan wore turtleneck shirts, button-front shirts or sometimes a striped shirt under a dark blazer—a look that's still trending today. Short or long, Bob Dylan's hairstyles are always a little on the unkempt side, slightly styled with a little curl. His looks often include a bit of scrubby beard growth.
Find a Halloween costume shirt
There's a fair chance you already have a Bob-Dylan-worthy shirt in your closet or one that's close enough to make it work. Look for a long-sleeve button-down shirt in any basic workman's clothing color, such as white or light blue. If you don't have such a shirt, choose one with narrow horizontal stripes instead. A dark-color turtleneck is yet another option. Many of Bob Dylan's looks involve wearing such tops under a jacket or blazer, so if you're going for that layered look, a short-sleeve shirt will do.
Find a blazer or leather jacket
While you're sourcing some shirts for your cosplay or Halloween costume, look for a dark blazer or a leather jacket. The black leather jacket could be virtually any type, such as one that looks like a blazer or that has fringe on the sleeves. Wear the jacket with your selected Bob Dylan costume shirt to see which option looks best. If you're going to a Halloween party and you're concerned about being hot in the costume, Bob Dylan sometimes wore a dark vest, such as a black leather vest, in place of the jacket.
Choose the pants, belt and boots
Basic blue jeans or black pants that fit like jeans have been part of Dylan's look throughout the decades. In many cases, he wore his shirt tucked into the pants and wore a dark belt with the pants. Dylan often wore Chelsea-style boots, which are ankle-high boots with either elastic or a side zipper for putting them on with ease. Dark ankle-high boots are a good choice that pairs well with any Bob Dylan costume.
Add the accessories
Just about any era of Bob Dylan costume includes a harmonica sitting in a harmonica holder around the neck. Add an acoustic guitar for the folk singer early Bob Dylan look or choose an electric one for a more rockin' midcareer Bob Dylan. A newsboy cap goes well with the early 1960s Bob Dylan costume.
Wear classic Ray-Ban-style black sunglasses to capture Dylan's look from any era. For the most part, Dylan's various styles changed little from the 1960s through the 1980s or 1990s, so there's lots of wiggle room for your DIY interpretation.