I used the following photo of fitness and glamour model, Denise Milani, as the starting point. Using the pen tool, I started with large, flat color shapes to create my base layers and clipping paths. As you can see from the work-in-progress images below, I built up the shadows, mid-tones, and highlights using different blend modes for each.
When it was complete in Illustrator, I imported it into Photoshop and overlaid a grungy, paper texture on top to give it a warm, antique-y feel.