How To Dress Like The 50s With Jeans

Jeans first became popular in the mid-1950s, especially with the younger generation. They brought about a whole new way of wearing clothes without having to always resort to a dress.

What Was Menswear Like In The 20s (1)

The high waisted styles replicated the nipped in at the waist look that was common back then. They were also often made of dark and heavy denim that contrasted with the thin fabric of the women’s tops.

However, jeans were popular with men and women during this era. It gave both sexes an adventurous way to dress that became more and more casual over time.

If you are looking to replicate the 1950s era of wearing jeans, then you will want to read on. Here we look at how to dress like the 50s with jeans. 

You will be surprised at how easy it is!

Who Are 1950 Denim Style Icons?

Whether you are watching the film Grease or are trailing the internet for 1950s fashion icons, then you will find plenty. From the likes of Elvis Presley and Marilyn Monroe, all the way to James Dean.

Jeans became an everyday staple for many. They allowed a person to dress a lot more casually than they were perhaps used to. They also promoted a particular type of style, often referred to as a ‘greaser’.

This style was particularly popular with the young American men of the 1950s. It included wearing jeans with white shirts and a leather jacket. The hair was often heavily styled in a slick way too.

They also took their inspiration from workwear, such as Dickies pants, a work-based jacket and a baseball cap. 

Women on the other hand volumized their updo and wore a pencil skirt, heels and a light top.

How To Wear Jeans Like The 1950s?


Women often wear jeans inspired by the 1950s. Here are a few key points when wearing jeans inspired by this stylish era:

  • For a smart casual look, team the high waisted jeans with a belt to nip the waist in more, and team it with a white blouse tucked in. 
  • Pair the jeans with a top that has a square cut cleavage line. This should not show cleavage, but just the skin above. 
  • Keep it simple by wearing a thin cotton quarter length sleeve top tucked into the waist of the jeans with a belt
  • You can also wear a T-shirt with jeans. Just remember to roll the ends up of the jeans with every style!
  • You may also want to think about footwear. This can include open-toe sandals, wedges and heels.
  • Some women like to accessorize with bandanas in their hair or flower clips. 
  • Use a thin belt with a thin fabric top. It will keep the waist looking dainty.
  • You could also try wearing pedal pusher style jeans with similar clothes to the above. Remember to still roll up the ends. Wear heels to elongate your legs, or flat shoes to give the outfit a casual look.
  • For a modern take, wear a leather jacket or varsity jacket.


It is easy for a man to emulate the 1950s era while wearing a pair of jeans. Often when it comes to males, the greaser look is the best way to go for inspiration. 

However, you do not need to do the full comb-backed hair and leather jacket to appreciate this style.

  • Wear the jeans rolled at the cuff with a plain white T-shirt. A black leather jacket is optional but always works.
  • Team the jeans with a button-down plaid shirt. 
  • Wear a varsity style jacket with a plain white T-shirt and rolled up at the cuff jeans.
  • Wear boat shoes rather than sneakers.
  • Accessorize with a nice belt and aviator sunglasses.

Final Thoughts

Jeans are a fashion staple, and have been through every single decade since the 1950s. The material is robust, and if the jeans are made with quality, then they can last for years if taken care of. 

Jeans were also a revolutionary item back in the 1950s. It gave male and females something to wear that made them different to their parents’ generation.

Over time jeans became a part of casual wear. Even to this day we wear jeans casually, and sometimes formally – it happens.

If you love the 50s era then you will want to know how to wear jeans the same way the young generation did back then. Hopefully this article has helped you.

Frequently Asked Questions

What Kind Of Jeans Did Women Wear In The 1950s?

Jeans were relatively new back in the 1950s, after Levi only releasing their ladies collection in the year 1934.

By the 50s, women were wearing dark and heavy denim in a high waist style (see also ‘15 Best 50s Theme Party Outfits To Try Today‘). In a similar way to the cocktail dresses (Check out Vintage Cocktail Dresses), the jeans helped them keep the small waist look. 

The jeans were wider on the hips and then tapered down the leg. Often the jeans were then rolled up at the end at the ankle.

What Did Women Wear Casually In The 1950s?

During the 1950s, a casual style started to become increasingly popular. The fashions at the time included relaxed blouses, tailored trousers and pencil skirts. Jeans also became popular among women and men. 

Bright colors and plaid were common too. 

What Was The Most Popular Style Of Pants In The 1950s?

During the mid 1950s the most commonly worn type of pants were the cigarette style. These were high on the hips, wide on the waist and tapered to the lower leg kind of pants.

There is also the pedal pusher style which are jeans that have the cuffs of the jeans halfway up the calf. 

Often people replicate these kinds of styles when they think of 1950s jeans.

Were Jeans A Popular Item To Wear In The 1950s?

Jeans became a fashion staple for the younger generation in the 1950s. By the year 1954, zippers were added for the very first time.

They soon became casual wear for teenagers.

Willa Price

Leave a Comment

Your email address will not be published. Required fields are marked *