Solar protection is an important public health issue because solar UV exposure can cause acute and chronic damage to the skin. Seeking shade is a convenient and commonly practiced sun avoidance measure. Shade works by physically shielding the skin from direct UV rays; however UV rays can also reach the skin from other angles. It is not clear how protective the widely-used shade structures like umbrellas and walls are under actual use conditions. In this study, a sky view model was applied to systematically assess the influence of different factors to umbrellas and walls, including the transmission of the shade materials, the reflectivity of the ground or the wall, diffused UV to total UV irradiance ratios, shade geometry, a person's positions and orientations in the shade. We measured the sunburn protection factor (SPF) with a calibrated UV meter at different positions in the shades of an umbrella at different times of the day and compared the measurement results with the modeling. We found that shade structures like umbrellas and walls are more effective when the ratios of diffused UV to total UV irradiance are smaller (mid-day). The effectiveness increases with more coverage, less surface reflectance, and more centralized positions in the shade. The SPF value for a typical umbrella is probably between 3 and 7 in real-life. The low sun protection level offered by a typical shade highlights the importance of educating the public about how to properly protect the skin from the sun and the importance of applying a combination of sun protection measures during extended sun exposures.