Skip to Content

The 20 Most Stylish Musicians of All Time

Regardless of the era, there’ll always be something effortlessly cool about musicians.

This post may have affiliate links, meaning we earn a small commission on purchases through the links (at no extra cost to you). This does not change our opinion but does help support the site. Thank you!

Granted, the 80s gave us a whole host of trends that nobody wants to remember, but even when the style du jour was questionable, there were still countless boldly fashionable men shining like dapper beacons to guide us out of the sorry mess.

From the 50s right up to 2019, here are 20 most stylish musicians who look as good as they sound.

Our 20 Favorite & Most Stylish Musicians

Bryan Ferry

From that velvet voice to the velvet suits, Ferry has always been smoothness personified.

Bob Dylan

A man who has continuously reinvented his look and his sound. From his denim and chambray Guthrie-esque early days to the iconic wayfarers and curls of Blonde On Blonde, Dylan is forever cool.

Keith Richards

In the Stones 60s heyday, Keith was an impossibly cool, ragged, jagged amalgamation of scarves, jewellery and cheekbones that could cut glass. Even in the 90s, Keith cut a raggedly dapper figure.

Marvin Gaye

Of course, Marvin could rock a dress suit like no one else, but look at him in that red beanie and denim shirt and ask yourself if there’s ever been anyone cooler. (There hasn’t.)

Childish Gambino

Is it sacrilege to suggest that Gambino (aka Donald Glover) is this generation’s heir to Marvin’s crown? We suspect not.

Chet Baker

Has anyone ever looked better in a white t-shirt?

Paul Banks

Banks and his band Interpol have always cut silhouettes as sharp as their basslines. A master of monochrome cool.

Matt Berninger

Berninger (of brooding indie darlings The National) is a big fan of a waistcoat, giving off a “cool and slightly eccentric history professor” vibe as he lurches around the stage spilling red wine. It works.

Jarvis Cocker

Back in the 90s, Cocker was the coolest man in Britpop. Twenty-five years later, not much has changed. He’s still a rakishly fabulous man with the best wardrobe in the country.

Levon Helm

Perhaps Dylan only asked The Band to collaborate so he could trade chambray with their drummer Levon, the finest singing drummer of all time and the man who defined American backwoods chic.

Albert Hammond Jr

Picking the most stylish Stroke would be as difficult as picking the worst Trump press secretary, if it wasn’t for Mr Hammond Jr. Somehow still making skinny ties and suits look great.

Hamilton Leithauser

The frontman of the sadly defunct The Walkmen combines white tees or shirts and black slacks to tremendous effect.

Bruce Springsteen

From his Pacino-in-Serpico bohemian early days to the all-American, all-denim glory days, Springsteen has always and will always be the coolest.

Dave Rawlings

Speaking of denim. Country crooner Dave Rawlings is a master of double denim, often setting the look off with a natty neckerchief and his trademark cream Stetson. Most people couldn’t pull this off. Rawlings can.

Leonard Cohen

The much-missed Canadian doom merchant was famed for his debonair style, rarely seen in anything other than a dark suit and a snappy hat. His grace and style are irreplaceable.

Thelonious Monk

Those wonderful, wonderful hats. It’s ok to be as difficult as Monk was when you look that good.

Nick Cave

With that long lean frame and long black mane, Cave could pass for the best-dressed preacher in the creepiest backwoods church in the darkest Southern Gothic novel. Fashionably menacing.

Frank Sinatra

The suavest man on the strip by a mile. Sinatra could stand next to Sammy D and Dean and still be the coolest man in the room. Perhaps the most stylish musician of all time.

Johnny Cash

Black. Black. Black. Maybe a white shirt if he was feeling cheery. Several buckets of pomade. A scowl. A cigarette between his lips. They don’t make them like big John anymore.

Miles Davis

Ignoring whatever the hell was going on with his 80s look, Davis dressed and carried himself with a style befitting the man behind The Birth Of The Cool.


Mark Grassick joins us with over 17 years' experience as a journalist covering pop culture in the UK and Ireland. He's interviewed everyone from Alan Rickman to Iron Maiden and is currently a bearded, music-mad father of two and husband of one residing in London, England.