Style Archives: Bob Dylan

Lookin' so dandy and so fine

Bob Dylan’s sixties style has been chronicled in great depth, and that’s good because he looked marvelous for pretty much the whole decade. As the ‘60s gave way to the ‘70s, Dylan’s style–like his music–evolved, and he started experimenting with leather jackets, khaki, head wraps, etc.. The ‘80s were a mixed bag for Dylan–both musically and style-wise. That being said, I’ll go ahead and insist that it was an underrated decade for him on both fronts. Since the ‘90s, Dylan has remained in the cultural conversation, and unlike other aging rockers, he has not let his style slip. Please join me as I dip into the Bob Dylan style archive.

When Dylan got to New York in 1961, his style reflected his midwestern upbringing. He wore simple button-down shirts, denim, hats–the sorts of garments his hero Woody Guthrie wore. But that would change.

In 1963, Dylan released his second album and first masterpiece, The Freewheelin’ Bob Dylan. This picture, taken in Greenwich Village, shows a different Dylan from the teenager we met in 1961. Though the outfit is practically the same, the striped t-shirt and rakish new haircut dial up the confidence a whole lot.

In the mid ‘60s, Dylan put together some truly iconic fits–and I guess his music was good, too. I won’t pretend to understand what’s going on with his collar, but he carries himself with unholy amounts of swagger. Look at the length of that cigarette ash! And need I add that his double breasted coat looks amazing?

Another pic from around that time. This one shows Dylan wearing Cuban heels like all the rockers started wearing after the British invasion. Dylan is a legendary wearer-of-coats, and this belted number is maybe even better than the double breasted coat we just saw.

When you put out a record as good as Blonde on Blonde (1966), you get to wear pretty much whatever you want, and that includes frilly polka dot shirts. Dylan will return to polka dots throughout his career. Please take note of the Coat God’s corduroy jacket, and of course, the shades. This is probably the Dylan haircut.

The times, they are a-changin’, and so is Dylan’s style. The year is 1968, and the palette is notably lighter. The fabrics are, too. We’ve got a lightweight oxford shirt, gray trousers, and some sandals that look about a size too small. The hat is divine. No, you cannot pull it off. Or maybe you can, what do I know? Swing for the fences, boys.

I should note that Dylan got into a nasty motorcycle accident in 1966, and that may have informed the change in his style. It seems to have informed everything else in his career.

Before I became obsessed with Dylan’s mid-’70s style, I thought this was the Dylan fit pic. Look at him staring off in the distance, just freaking chilling on the Isle of Wight. A more structured oxford shirt, cropped pants, loafers, and a mothereffing mustache. Lord have mercy.

The seventies are here, and so are the lapels. Otherwise, this picture is relatively unremarkable. Next.

In the words of VH1, I love the ‘70s. A lot to take in here, so I’ll draw your attention to Dylan’s flared jeans–back then, people called them “bellbottoms.” Wild. Where do we turn now? The return of the polka dot shirt? The mighty necklace? How about that leather jacket? Dang. And I’m not even convinced it’s ethical to wear leather. Dylan’s sunburst Telecaster–a less angular guitar than the Strat from the last pic–mirrors the tan, round crown of Dylan’s hat. This is too good. Let’s keep going.

I’ll spare you pictures of Dylan sporting whiteface during the Rolling Thunder Revue. You’ve seen those. And though you’ve probably seen this outfit, too–Dylan wears it during the Hard Rain concert film–I’d like to sing its praises for a sec. The head scarf is one thing, but did you notice the beaded capo? The tasteful signet ring? The texture on that button-down shirt? Note: the “Idiot Wind” recording that emerged from this concert is one of my favorite things ever.

Who among us hasn’t flirted with Christianity? I was confirmed by the Catholic church, and I even joined a youth group before lapsing and finding shelter in the cold but logical house of atheism. Saved!

I never did wear a leather vest.

The Coat God has risen, alleluia. Impossible for me to not immediately think of Shia’s Sundance fit from last year. What’s the over/under on Dylan wearing Golden Geese? Probably zero given that the brand was established in 2000. This picture is from the early ‘80s, I believe.

Yeah, the eighties are here, but Dylan’s fits aren’t embarrassing yet. I love the boots, and I really love the drape of his coat. The rolled sleeves look super cool. You don’t see him do that too much. Yes, he is wearing eyeliner.

No comment.

I’m not mad at this look, just like I’m not mad at Empire Burlesque (or Knocked Out Loaded, Infidels, Oh Mercy…). The fabric is pretty out there, and Dylan never looks quite so comfortable as when he’s wearing black, but this was the style back then. The backlighting is, frankly, not great.

The year is 1994, and Dylan is recording an Unplugged session for MTV. He’s in arguably the biggest slump of his career, having released Under the Red Sky (1990), Good As I Been To You (1992), and World Gone Wrong (1993) to tepid reviews. He retreats to his trusty polka dots, perhaps to channel whatever it was that made him so virile in the sixties. The shades are back, too. Something is happening.

At the 1998 Grammys, Dylan took home the top prize for his late-career masterwork, Time Out of Mind. His performance was hijacked by this Soy Bomb fellow. You remember. Anyway, that’s probably for the best because his outfit, surprisingly, wasn’t anything special. I do love the neck bow (as opposed to a bow tie), but the long, shiny jacket buttoned sky high just doesn’t do much for me. The piping on the pants? Nah. He still dresses like this today, but he’s made improvements.

Much better. This was taken near the release of Love and Theft. Outstanding ‘stache.

When Dylan returned to the Newport stage in 2002, he looked like a bedraggled cowboy. Straightened hair? Check. Ornate vest? Check. Ten gallon hat? Yeehaw.

Well, the years started coming, and they didn’t stop coming. Bob made it to the aughts when so many of his peers didn’t. His three songbook albums (2015’s Shadows in the Night, 2016’s Fallen Angels, and 2017’s Triplicate) are rare birds in that they don’t suck. Every other artist sucks at making them. And now Bob is really leaning into western wear. Bolo ties, cowboy hats, mother of pearl buttons, and so forth. A good look on him.

Here’s Bob playing the penultimate episode of Letterman. People didn’t seem to like it, but they were wrong. It was a dignified performance. His band sounded great. And Bob’s still rocking these incredible droopy neck bows on shirts with huge collars so I’ve got nothing to complain about.

Last month, Dylan released his latest album of originals, Rough and Rowdy Ways. The lead single, a 17-minute elegy called “Murder Most Foul,” is the best song of the year. Bob is the king. If you’ve made it this far, no doubt you agree. I don’t see him letting up–not in terms of clothing, anyway. I doubt he’ll reinvent his style again, but as long as he’s serving fits like the one you see above, I’ll be pleased. Give this man a Nobel Prize, a Nobel Prize for getting fits off.