Men's 1950s Vintage Shoes

In the 1950s, men had several types of footwear to choose from. Most men from this era were as clean cut and conservative as their shoes. On the other hand, the rebellious youth preferred making dramatic fashion statements with their expressive choice of footwear. Many styles of authentic men’s 1950s vintage shoes are still popular and in demand today.

Loafers

Loafers were popular in the 1950s, and when college students began placing a penny inside the strap of the shoe, they became known as penny loafers. Businessmen began wearing a new type of loafer, which had a tassel attached to the top of the shoe.

Oxfords

Traditional men in the 1950s often wore lace up oxford shoes. Brogues were a type of leather oxford with small ornamental holes patterned along the edges of the shoe. Wingtip oxfords, also called full brogues, had a pointed toe with decorative wings running down from the toe to the sides of the shoe. Nubuck oxfords were made from nubuck, a material comparable to suede.

Chukka Boots

Inspired by military boots, ankle length chukka boots or bucks were worn as casual wear in the 1950s. This type of footwear had two or three eyelet holes for laces and was most generally made out of suede.

Brothel Creepers

These men’s 1950s vintage shoes had a style similar to loafers, but with a thicker heel and a clunky appearance. Radical youths wore them with tight-fitting pants, a drape jacket and a bolo tie. Brothel creepers were most often black, white or both colors combined.  

Chelsea Boots

Chelsea boots had elastic sections on each side which was later replaced with a zipper. These ankle high leather boots had a 2-inch Cuban heel.

Winklepickers

These shoes looked similar to oxfords with a low heel and tie laces. The main difference was the sharp, long, pointy toe of winklepickers.