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.
Using a little light back-combing along the way if you need to, and spraying some hairspray along the way will help, guide the hair so that it starts to curl around, using your fingers to help guide the strands in place. When in position, hold with bobby pins, and if you have blonde hair, use blonde pins to ensure they’re not too visible. Black pins look very obvious sometimes and can spoil the look. Spray with hairspray, pin the remainder of the hair up, and add a scarf for a real pinup touch.
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."