Pin-up fashion is synonymous to and a combination of Burlesque, Rockabilly and Old Hollywood Glamour in terms of clothes, hair, makeup, shoes and accessories. It's all about being classy yet elegant, flirty without going overboard. It's more on minimalism and simplicity with just a little skin exposure. With a little cleavage men are teased. This style celebrates women, from their curves to their flawless faces. Don't worry if you think you aren't skinny enough to pull off the perfect pin up girl look. The pin-up  culture embraces your natural hips and curves. 
_{I think this is a great look for a beginner or someone with an advanced skill set. The best advice I can give when it comes to creating rolls is, when you think you’ve teased it enough, tease it a little more. I find that most people are afraid to tease their hair. With vintage styling, I find teasing key. I recommend using a texturizing power like Puff.Me at the roots then teasing with a “C”-shaped motion. Lightly brush out the surface and use a pomade or wax to smooth flyaways.}
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."