Men's Shoe Styles From the '50s

Written by a.n. pike
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Men's Shoe Styles From the '50s
Loafers have maintained their popularity over the years and have undergone many re-imaginings. (Hemera Technologies/ Images)

Shoes go in and out of style with the changing of every season. During the 1950s, men were just beginning to wear more flamboyant and eye-catching shoes such as the winklepicker and an assortment of ankle boots. While not all of the men's shoes from the 1950s have stood the test of time, many have maintained their popularity, such as the classic basketball shoe and the loafer. Other men's shoes from that era have inspired many trends over the years.


Winklepickers were ankle boots and shoes that had very low heels and very long, pointed toes. The shoes usually had a side strap or buckle. Winklepickers were inspired by British rock 'n' roll musicians. Winklepickers were popular among the rebel youth of the 1950s. The shoes were most often seen in black, two-toned brown and white or the contrasting colours of black and white.


Chelsea boots grew in popularity toward the end of the 1950s. Chelsea boots were ankle boots that had two elastic panels on either side or one elastic panel on one side of the boot and a zipper on the other side. The boots were popularised by The Beatles. Chukka boots were inspired by the desert military boots that were worn in World War II. Chukka boots were ankle high and made of suede or leather. The boots had two or three lace holes toward the top of the boot. Chukka boots were popular among the 1950s street culture and have gone in and out of popularity over the years.

Loafers and Creepers

Loafers were popular among the well-off and privileged college students in the 1950s. They were easy to slip on and normally made in brown or brown with a white strap. Penny loafers became popular when someone slipped a penny into the strap across the front of the loafer. Loafers have maintained their popularity over the years with both men and women. Creepers featured thick crepe heels and resembled a large loafer. Creepers usually had a buckle or a strap and were popular with the youth of the 1950s. Creepers often came in solid black or white as well as a combination of both. Creepers are still popular among the rockabilly crowd.

Athletic Shoes

Basketball shoes such as high-top Converse and P.F. Flyers were popular among the youth. Basketball shoes were worn not only during sports but as part of street clothes attire as well. While they are not used as basketball shoes any longer, the original basketball shoes have maintained their place in culture over the years.

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