19 rock stars who were the most stylish men of their time

What do Bob Dylan, Simon Le Bon and Donald Glover all have in common? (Hint: More than a string of chart topping hits).

Dylan's upcoming Australian tour reignites a fascination with the music industry's most revered – and potentially underrated –style icons from the past half-century. The effortlessly cool? The charismatically contentious? Here's why we're still talking about them…

Blue suede rebels (and gents)

Prior to the bedazzled jumpsuits, Elvis adopted a laid-back approach in the '50s. He paired raw denim or high waisted trousers with Cuban-collared shirts. The King knew exactly what looked good on him and dressed accordingly.

The '50s also re energised sartorial silhouettes as the tailored suit became the gentleman's hallmark. Often overshadowed by Rat Pack heartthrob and mortal enemy Frank Sinatra, Bing Crosby demonstrated that an impeccable pin-striped suit, a fedora and a twinkle in the eye never go out of fashion.

Fur, guitars and cool cats

The '60s saw music makers like Bob Dylan and The Beatles evolve into style sensations in the way they cultivated an air of effortless confidence. "All I can do is be me, whoever that is," Dylan reflected in 1965.

He appeared utterly at ease in his go-to outfit of a turtleneck sweater, leather pants and Ray Bans. Throw a brown trench over the shoulder and there it is; Zim' swag. 

"His style 'mojo' was another expression of his creativity as an artist," says Monte Morgan of Australian indie-pop duo Client Liaison. "People often don't realise that there was a genuine element of theatre to him."

Post Beatlemania, Ringo Starr also mastered the art of the upmarket hippy. While paisley suits, pastel cardigans and fur flourishes were more flamboyant than Dylan's outfits, both men embodied the persona of '60s nonchalance that inspired countless designers including Tom Ford and Hedi Slimane.  

Ziggy business

Outer space. Metallic tights. Bless you, Bowie.

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Granted, the Ziggy Stardust look was pretty intense. But it's worth reflecting on how Bowie inspired a generation of '70s fans (and far beyond) to take risks with colour, texture and excess when it came to style. Push the boundaries. Keep 'em guessing…

Shift focus to German electro-pop band Kraftwerk and their dynamic move towards minimalism across both music and style. Sharp shirts, starched collars and crisp trousers; Kraftwerk made average fashion 'the thing'. The band had a significant influence on fashion designer Raf Simons, who named his Autumn/Winter 1998 collection after their song Radioactivity.

The glory of the '80s

Ask any fan who was caught up in '80s Durandemonium and they'd have a few words for you: Simon Le Bon. The Duran Duran frontman redefined sex appeal through matching ensembles like the white jacket and cropped white pants. Safe to say his golden mane and sculpted cheekbones never went unnoticed either.

Synth-pop duo Pet Shop Boys played the opposite style card. They used mystery as the main component of their style ethos. Cue massive overcoats and black sunglasses. The duo inspired numerous designers to explore the notion of identity in fashion; selected by Dior Homme's former creative director Kris Van Assche to front the brand's SS18 campaign.

Brits and beats

As rap and hip-hop music made their way into '90s mainstream culture, no one melded street style and high fashion quite like Tupac Shakur. Often seen in statement garments by Versace and Jean Paul Gaultier, Tupac's bandana-baggy jeans-jacket (no shirt) defied style conventions.

The graphic t-shirts, bucket hat, oversized denim and occasional hint of lux favoured by British producer and Blur frontman Damon Albarn. The soccer-loving Pom was kicking the dad shoe trend before it had even been noticed by the cool kids.

Heart on their striped sleeve

All bets were off when it came to men's style in the new millennium. The Killers frontman Brandon Flowers had his way with every colour and cut of blazer imaginable, while unlikely babe-magnet Pete Doherty had us all musing upon the secret alchemy behind filthy ripped shirts and trilby hats.

The 'emo' subgenre also gets dishonourable mention. Thanks (or not) to bands like My Chemical Romance, a generation of young adults squeezed into skinny leg jeans and blackened their eyelids in a show of badass defiance against the 'institution'. We move on.

This is the modern man

Childish Gambino aka Donald Glover is one of the best dressed men in music today. He's a style chameleon; kicking it in streetwear one minute, effortless in Prada the next. Few people look absolutely at ease while wearing an open Hawaiian shirt on stage or a brown velvet suit to the Golden Globes. But Glover does.

Australia is not without representation today, either, with Troye Sivan one of the many young men breaking down "masculine" stereotypes, both with music and his fashion sense. Fond of a Prada shirt, a playful print and pastels (going so far as to dye his hair a matching shade), Sivan has fun with his fashion. And that's the most important detail of all.

Check out the gallery above of the biggest style figures from decades gone.