Drawing a retro style pin up can be a little tricky in that you do not want the image to come off as pornographic. There is a fine line between sexy pin ups, and trashy drawings of girls. The first thing you have to consider is body language. The position of the figure in a pin up should be interesting and unique. It should have a sense of movement to it to make the figures seem more life-like. Here are a couple examples of figure positions. Notice how both figures are doing something interesting with their hands - putting the hands above the head is a classic example of how to make the image more dynamic.
A few more examples of figure positioning. Don't be afraid to have fun with it. Pin ups are known for featuring women in unusual and borderline cheesy situations. Adding in a small detail such as a ray gun or a soda bottle completely changes the story behind the image. The outfit is also very important and can help tell the story and establish a sense of setting. When utilized appropriately, giving a figure gloves or stockings immediately makes the image sexier. Pin ups do not always have to feature a full figure, but can sometimes feature just the upper part of the body. So long as it's sexy and interesting, anything goes!
The female figure should be drawn roughly eight heads tall. Use high heels to help make the legs appear longer. Even if your figure is not wearing heels, it is a good idea to have the figure standing on tips of their toes rather than have the heels of the feet touching the ground. Having the foot flat on the ground is not as elegant.
In addition to giving the figure heels, there are a few other key elements that make a retro style pin up distinctive. Since pin ups became popular in the first half of the 20th century, the clothing and hair are very important, as is the makeup. Be sure that these elements are reflective of the time period you are going for. Remember that even swimsuits and lingerie should leave plenty to the imagination - a good pin up should not have to rely on nudity to be sexy. The makeup should be fairly bold and the hair should be thick and full of movement. Notice how interesting the position of the figure is here - it is more fun seeing the figure leaning back on a stool with her legs crossed as opposed to just sitting there with a straight back and knees together.
The eyes are an incredibly important aspect of a pin up. Draw long, thick lashes and make the eyes partially closed, as if to seem slightly careless. The attitude is in the eyes - they need to exemplify confidence above all else.
Make the lips full and pouty. If you want to give the lips a shine, color the lips in with solid black and then white out spots where the light hits. This will give them a wet look.
Now we can begin working on our figure from start to finish. First, let's lay down the rough construction lines by using a 2H or harder pencil. Drawing very light, create a basic stick figure of the model. These lines to now have to be perfect - they are just a guide for us to go off of and they will be erased later on.
After the construction lines have been sketched in, we can now start working on the face. Having her look back over her should will create a sense that she is flirting with the viewer, even more-so if she is looking directly at us with her eyes. You can start sketching in the hair, but we will finish doing the hair in step 10 because we first have to draw her right arm…
When drawing the arms, be sure that you plant the right elbow firmly on the ground, as it is supporting her upper body. The left arm will be hidden by her body, so only draw the forearm and hand. Having one hand rest on top of the other helps make the image more interesting and natural than if they are laying on the ground separately.
Now that the arms are drawn in, we can revisit the head to finish drawing the hair. Now you can see why we drew the arms first, because the hair partially falls in front of the right shoulder. Make sure that the hair is thick and voluminous. We will go back to the hair later, after we ink, and add in highlights for shine.
We can now start making our way down the body by drawing in the torso. She's going to be wearing a one-piece swimsuit for added sex appeal. Although the swimsuit is form fitting, it should still have a few small wrinkles around the waste.
Draw in the legs and make the feet point upwards to add more character to the image. Give her some heels for fun!
Now that the image is sketched out we can ink it using a brush or Micron markers. Carefully and patiently ink over each line. After the ink has dried, erase your pencil marks with a kneaded eraser. Look at how nice and clean your image has become!
To make the image even more unique, add in small polka dots to the swimsuit. Do your best to make the pattern of the dots contour to the shape of the figure.
Go in and add shadow to the image to give it a sense of depth. Don't go too heavy on shading - you don't want it to be so bold that it takes away from the delicacy of the model. Keep an eye on your light source. In this case, the light is coming from the upper left side of the page.
Finally, use a brush with opaque white paint or white ink to add highlights to the hair, or do any needed touch ups. Be sure to give the hair a lot of shine and keep in mind that the light is going to hit on the same side of every curl and hair roll. And that's how you draw pin ups! Hope you enjoyed it!