The performance of elastomeric seals degrades over time in use due to the development of permanent material deformation. The existence of localized high stress regions below seal-housing contact areas led to consideration of improving O-ring design by modifying material behavior to decrease strain energy, and so permanent deformation, in these regions. Photoelastic stress analysis was used to experimentally characterize the stress and strain fields in O-ring sections and to validate finite element models used in design studies. O-ring section designs that included small inset regions of different material behavior than the larger surrounding section were investigated with the intent of manipulating and reducing the strain energy content. Finite element models of O-rings were used to characterize the strain energy content and distribution for inset materials with various stress-strain behaviors. Measurements of permanent deformation and load-deflection behavior of specimens held under applied compression over time showed dependence of the amount of permanent deformation on strain energy. Design rules were extracted from results of studies in which inset region material stiffness, stress-strain behavior, size, and location in the larger section were varied. O-ring sections with regions of less stiff material result in lower strain energy and more uniform strain energy density distribution than the typical one-material seal. Inclusion of less stiff softening stress-strain behavior material insets in the larger O-ring section produced reduction in strain energy level and favorable redistribution of the high strain energy density regions compared with the conventional one-material one-material-behavior design. Similar concepts will apply to the design of other elastomeric structures in which permanent material deformation affects structure performance.