1 The first thing I do is put down the midtone. Use this opportunity to paint in the main shape as accurately as you can. Silhouettes are an important tool in communicating form, and this is great chance to get it right before complicating things with light and shadow. 2 Study reference to get a feel for the type of leather you’re painting. Soft, turning folds need smooth edges, while sharp kinks can be handled with hard, bold strokes. When a surface folds, the creases that form will be getting less light. The deeper the crease, the darker the shadow. 3 For a glossy look, strong light should show where reflections would go. On leather this is often the crest of each fold. Be sure to paint the surface textures that are revealed in the light, particularly in the transition from light to halftone. This keeps the material from feeling too smooth.