Visit local modeling companies in your area and look for models who meet your basic requirements. Pinup models have curves and feminine figures, unlike the stick-thin models or models with boyish figures in the modern era.
Purchase vintage clothing from thrift stores and vintage clothing shops that fit your model and the style of your photographs. Women in pinup photographs typically wear little amounts of clothing and show quite a bit of skin. Look for outfits that reveal cleavage and a lot of leg.
Scout locations in your surrounding area. Pinup photographs feature a wide range of backgrounds, including ocean settings, kitchen settings, garages and even on cars or ships. Look for locations that complement the coloring of your model as well as her clothing.
Pose the model in a lighthearted and humorous way, such as sitting on a stool with one leg raised slightly and tipping her hat to the camera. Try different poses, finding ways to bring out the both the youthful and sexy sides of your model.
Change the backdrop and setting for each model you work with, giving each woman her own niche or market. For example, pose one woman in outdoor settings, another on a motorcycle or car and make boudoir photographs or bedroom images of a third model.