Modern pin up girls provide plenty of inspiration for how to wear 1940s and 1950s pin up dresses in a fresh way: Mix and match swing dresses with colorful fluffy petticoats and a hair flower.  A wiggle pin up dress ads a sexier variety that can also be office appropriate with a matching jacket. Don’t forget seamed stockings and a comfortable but oh-so-sexy pair of wedge heels or casual ballet flats.  Think beyond the pin up dress with high waisted pants and shorts or swing skirts and tops. Use the 40s and 50s menus at the top for more pin up clothing.
While victory rolls, vintage waves and micro bang hairstyles were ultra-popular styles back when pin-up girls and screen sirens reigned supreme, these same fun, flirty looks can be worn today. It doesn’t matter if you’re wearing it as a style for Halloween or for a special occasion; all of these styles are wearable and fairly easy to create. To look like a bombshell calendar girl in modern times, here are some pin-up styles for long hair that you’ve got to try out:
Gently flatten the back of the roll and curls under to close off the back of the victory roll (since this is the more traditional look that we’re going for), making sure to bobby pin well! Shape the front of the roll as needed, make sure to bobby pin the roll from the inside out, and spray well with hairspray. Repeat step #3 and #4 with the other side, and your rolls are done!
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."