Do you or did you used to work in an office environment? Then you're bound to own a pencil skirt. The classic pencil skirt is a key piece to bring to a pinup shoot as it's very usable and can be worn with shirts and cardigans or even just with your favorite bra. It is reminiscent of 1950s wiggle dresses that made the wearer walk with a little wiggle in their step.

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The classic style of the pin-up originates back from the 1940s. Due to the shortages of materials during WWII, this period of makeup is considered the "natural beauty" look.[20] The US was immersed in war-time economy, which put distribution restrictions on consumer goods.[21] General rationing was supported; women applied mild amounts of products. Despite the rations, "Women were encouraged to keep buying lipstick and to send letters to the front covered in 'lipstick kisses' to boost the morale of the soldiers."