How to Dress Like You’ve Stepped out of the 1950’s

1950s mens style

The 1950s was an era that many of us like draw style influence from. This simple style guide will show you how to pull off that 1950s mens clothing and fashion with ease this and every season. Men’s fashion in the 1950s is as popular now than it was back then.

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During the 1950s there was a style revolution. No longer were we in the troubled times of the war and people could start to finally wear what they wanted without it being drab and dark. The biker culture was well and truly alive and many of the younger generation wanted to rebel against the system and get into trouble.

This particular decade is solidified in the classic and brilliant (to me) film Grease. Danny Zuko with his slicked back hair, biker jacket and jeans makes him the heartthrob of the time, and his style can still be seen in today’s fashion world. Music plays a massive role in this decade with the likes of Elvis Presley and his swinging hips paving the way for that rock ‘n’ roll style.

1950s Mens Fashion: The Biker Jacket

The leather biker jacket is a classic staple item that nearly all of us have in our wardrobes. Like most fashion items that we see today they stem from practicality, but it takes that one brave soul to wear it for purely style purposes.

Brands like Schott NYC were the first to create the modern biker jacket. The Perfecto jacket was the first of its kind because the Schott brothers decided to put a zipper on it instead of a pop button fastening. Being made entirely from leather it was durable, hard wearing and immediately embraced.

lucky blue smith 1950s style men
Lucky Blue Smith channelling the 1950s


How to Wear Leather Biker Jacket

The leather biker jacket is a staple in many men’s wardrobes. Its versatility and durability speak for itself. Dress it up with a crisp white shirt and 1950s style trousers for a more formal look, or dress it down with a T-shirt and some jeans, either way, the leather biker jacket for men if the perfect wardrobe essential. 

leather jacket street style mens
A man wearing a leather jacket


1950s Rock and Roll Fashion: T-shirts and shirts

Steering away from formality and more into the casual vibe, the 1950s is the era where we had a lot of firsts. Casual T-shirts and shirts were worn with jeans and trainers rather than trousers which is epitomised in James Dean, who was a pioneer for the casual style.

Teaming plain white tees and shirts with a pair of raw denim jeans he was rarely seen in trousers or a more formal look. Stripes are a big game player during the 1950s, considered a classic style now they were first worn casually and for style purposes during the 50s.

How to Wear White T-Shirt

On the subject of white t-shirts, let’s take a page out of the book of James Dean’s iconic style. While it’s the ultimate basic with a basic look, it’s a timeless outfit. While keeping in the essence of 1950s, simple pair a slim-fit white t-shirt with either an Edwin or Levis 1950s jeans. Whether you opt for darker blues or lighter washes, this look is easy to dress around for any season.

the idle man James dean white tshirt mens 1950 fashion
James Dean in a white T-shirt



The 1950s was a time when we first started to see a pair of jeans for purely fashion purposes. Jeans were invented for practical use when the farmers and the working classes used to wear them whilst out working as the material was hard wearing and durable.

Since then brands such as Levi’s and Edwin have paved the way for jeans to become the staple item that everybody wears. For that ultimate in 1950s nostalgia try wearing a raw denim pair, classic and they suit everyone.

mens jeans 1950 mens style
A man earring jeans and a white T-shirt in the 1950s


If you are feeling adventurous. elevate your 50s look with some modern continuity. This means don’t just go for the denim jacket, but also opt for the matching trouser as well. The best way to create this look while staying completely authentic is avoid your day to day denim and invest into the Levi’s Vintage clothing range.

the idle man denim trend men
A model wearing double denim



During the 1950s you can see that the younger generations were steering away from the formality that was once the fashion. Trainers or plimsolls became the mainstream footwear amongst many, but they did still keep that slight hint of formality by wearing penny loafers and brogues.

Converse is a brand that many associates with certain subcultures within fashion, but their beginnings are different from their stance now. First created as a cheap and durable shoe option for the poorer families they soon became a hit amongst many. They moved into sports shoes and were endorsed by a basketball player named Chuck Taylor (can you see where I’m going with this?).

white tshirt history the idle man converse
Basketball players wearing Converse trainers


They fast became popular amongst the youth during the 1950s with many of them teaming them with a pair of jeans and a plain tee. However, this doesn’t mean that they couldn’t still be smart as loafers and brogues were still as popular as ever. Pairing some penny loafers, such as these ones from G.H.Bass & Co, with some white tube socks, raw denim jeans and a plain tee, you can have a 1950s mens look in no time at all.

Get the Look: 1950s Men’s Fashion

  • Be adventurous and opt for fabrics such as denim and leather.
  • Always opt for classics Levi’s and Edwin.
  • 1950s was the birth year of the most timeless wardrobe pieces.
  • Experiment with your basics, such as t-shirts.
the idle man jeans denim mens street style
A man wearing a leather jacket and light-coloured jeans

On That Note

The 1950s was a decade where we saw many firsts. We first started to see jeans and leather jackets for fashion instead of practicality. We also first started to see the mixture of the new and old i.e. penny loafers with jeans. We saw that people still wanted to keep the old traditions of dressing but liven them up in a new and modern way.

Personally, I love the 1950s way of dressing. I love the classic feel it has and the simplicity of it all. Teaming a plain white tee and raw denim jeans with some penny loafers, it gets no better than that!


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The 1950s was an era that many of us like draw style influence from. This simple style guide will show you how to pull...
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