There’s something sassy about this look. The women I’ve done it on have all had such great reactions to seeing it on themselves. It’s like it gives them permission to be a bit cheeky. When you think flapper or pin-up, there’s definitely an attitude associated with it. One thing I would definitely tell my client is that this isn’t your everyday look. The outfit has to match! I’m not saying you need to wear a flapper dress or a pin-up corset, but this is a classic look and you wouldn’t want to pair it with something too modern.
First and foremost, you’re going to want to start from the top, literally, your hair is up first. There are several different hairstyles that you can choose from but, some of the most popular can be a little bit daunting at first when putting together the perfect look to go with your pinup dress. If you want to go the easy route, be bold and cut in some Betty Page style bangs and flat-iron your beautiful locks for an edgy but simple look. But, if you’re more daring, maybe you want to try your hand at some victory rolls. First, you’ll curl your hair, dab some gel onto the roots of your hair and loop your hair using your fingers into rolled curls. You can twirl whichever direction you want to, but it’s most common to curl the rolls inward for a symmetrical look. Pin them in place from front and back, spray with some hair spray or liquid gel. You can now take out the pins or leave them in for some added strength.

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."