The Most Stylish Men of the 1950s

The 1950’s were a formative era in menswear fashion. Read on to take a look at the men who defined this time in fashion who have come to be considered the most stylish men of the 1950’s.

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I know what you’re thinking, Danny Zuko and Kenickie with their T-Bird leather biker jackets chatting up the Pink Ladies, but 1950’s men’s fashion laid the foundation for menswear standards that have lasted till now. Slicked quiffs and the pick of Hollywood’s most stylish and beautiful women is what many of these men were accustomed to, but the 1950’s style has influenced fashion that we see today, with recurring trends easily worked into your wardrobe.

James Dean

We couldn’t have the most stylish men of the 1950’s without including James Dean. Known for his strikingly good looks and onscreen demeanour, James Dean epitomises the 1950’s fashion. With simple and tailored looks he lead the pack when it came to the young guns in Hollywood, a look that is still worn today, simply classic.

PHOTO CREDIT: Harper’s Bazaar


Buddy Holly

Buddy Holly was not only one of the most influential musical acts of the 50’s, he was also of the the most stylish men of the 50’s. He embodied the 50’s style that characterised the time period. His signature thick-framed eyeglasses, cigarette pants, and smart jumpers would become pieces that soared in popularity and defined an era in fashion. Holly’s style influence is instantly recognisable even today as designers like Gucci turn out nerd-chic looks on the runway.

PHOTO CREDIT: Famous People


Marlon Brando

Famous 1950’s icon Marlon Brando also had great style. Most well-known for sporting plain white T-shirts, he helped the T-shirt‘s status in the fashion world go from strictly an undergarment to everyone’s top wardrobe staple. Actually, he effectively changed the whole fashion game for men. In the 40’s men wore smart suits to be on trend but once Brando took over the silver screen wearing T-shirts and leather jackets, everyone was after his look.



Elvis Presley

The king of rock and roll was a powerhouse when it came to style. Before the days of the bedazzled jumpsuit, this 1950’s man rocked a more preppy and tailored style. This look was sought after by many, allowing him to lead the way in the style stakes. Pairing tailored trousers with loose fitting shirts and boat shoes (classic 1950’s style shoes), he championed the preppy look. His swinging hips and talent for music was contagious, as was his style. He will always be on our style mind (reference intended).

PHOTO CREDIT: The Fashionisto


Frank Sinatra

Understated yet stylish are the best words to describe Frank Sinatra. His impeccably tailored suits – like most men’s 1950’s suits – and tipped trilby are definitive of his style, always dressed to the nines and ready for an impromptu song. More of a mainstream fashion icon of the time, he was the average man’s go-to when it came to style heroes, keeping the conventional ideas of the time, with his attitude doing all the rest.

PHOTO CREDIT: letsgetfisico


Montgomery Clift

Monty pioneered the casual vibe in the 1950s, teaming casual striped T-shirts and chinos for the ultimate in 1950s cool. Known for his relationship with screen siren Elizabeth Taylor, Montgomery loved teaming casual wear and tailored pieces creating an enviable wardrobe.



The Most Stylish Men of the 50’s

  • James Dean is a 1950’s icon who embodies the essence of effortlessly casual style.
  • Buddy Holly, one of the most influential musicians of the 50’s, was also quite a smart dresser. He perfected the nerd-chic look that we still see on runways today.
  • Marlon Brando, notorious Hollywood bad boy, revolutionised the plain white T-shirt from being worn as an undergarment to being one of the top modern wardrobe staples.
  • Elvis Presley, famous for his glittery jumpsuits, was quite stylish off stage ass well. He is another figure we still look to for 50’s style inspiration.
  • Frank Sinatra knew how to rock a suit – his signature look – in true 50’s fashion.
  • Montgomery Clift had the 50’s casual vibe down, pairing laid-back pieces perfectly.

On That Note

The 1950’s were a key period in setting the standard for menswear fashion. Many of the styles that we still see today were born in this era. The style icons featured are known for how they made waves in the menswear world at the time and to this day are considered the most stylish men of the 1950’s.