The friction of microstructured polydimethylsiloxane samples against a glass surface is studied through force measurements and simultaneous optical microscopy. Both average friction forces and the amplitude of stick-slip oscillations are greatly reduced by the structuring. Optical microscopy reveals waves propagating through the contact in connection which stick-slip events. The experimental observations are interpreted with the help of simulations of a spring-block model for which parameters are directly derived from the experiment. Stress gradients across the contact area are found to play an important role for the frictional behavior.