1950s Fashions With Rolled Up Jeans

Updated November 21, 2016

Jeans, or dungarees as they were called, caught on big in the 1950s. Teens never wore them to school or for proper social outings, but they often wore them to lounge around the house. As the decade wore on, Hollywood stars wore jeans in films, and they became popular outside the home. Young people wore them rolled up to achieve the height of cool.

Over-sized Dress Shirts

Young women wore oversized men's shirts with rolled-up jeans. They rolled their jeans halfway up their calves and wore them with white bobby socks and saddle shoes or canvas Keds sneakers. They borrowed white dress shirts from their brothers or fathers and left them casually untucked over their jeans. As the style developed and girls wore jeans outside of the home later in the decade, they unbuttoned the bottom buttons and tied the shirt tails in a knot at their waist.


Girls and women fell hard for colourful cashmere sweaters in the '50s. They wore baggy pullover sweaters long over their jeans around the house or for very casual outings. They wore cardigan sweaters over feminine blouses with rounded Peter Pan collars that were tucked into their rolled up jeans. These sweaters were often lovely pastel shades and came to the waist or hips. Teen girls also wore cardigans tied loosely over their shoulders and around their necks with blouses and jeans.

Sleeveless Shirts

In the second half of the '50s, when it was more acceptable for young people to wear jeans and more relaxed styles outside of the house, young women rolled up their cuffs and wore them with sleeveless shirts to picnics and casual outings. Patterns like polka dots and especially gingham were trendy and girls wore sleeveless shirts or halter tops that tied around their necks with their jeans and dainty ballet flats.

Guys Fashions

Young men took a cue from stars such as Marlon Brando and James Dean and rolled up the cuffs of their jeans in the new, cool style. They sometimes pegged their cuffs by folding them in before rolling them up to make them tight. Guys wore rolled jeans with white socks and loafers or Converse high-top tennis shoes. Along with this style, they wore T-shirts and varsity jackets or letterman sweaters. Young men into the greaser style wore their jeans with black boots and black leather jackets.

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