Smart window has immense potential for energy savings in architectural and vehicular applications, while most studies focus on the tunability of a single property of optical transmittance. Here we explore harnessing dynamically tunable hierarchical wrinkles for design of a potential multifunctional smart window with combined structural color and water droplet transport control. The self-similar hierarchical wrinkles with both nanoscale and microscale features are generated on a prestrained poly(dimethylsiloxane) elastomer through sequential strain release and multistep oxygen plasma treatment. We show that the hierarchically wrinkled elastomer displays both opaqueness and iridescent structural color. We find that restretching/releasing the elastomer leads to the reversible and repeatable switch from opaqueness to transparency, arising from the flattening of large wrinkles (micrometer scale), while a nonvanishing structural color occurs due to the nondisappearing small wrinkles (nanoscale). The unique features of combined reversible large wrinkles and irreversible small wrinkles during hierarchical wrinkling are well reproduced by corresponding finite element simulation. The criteria for generating self-similar hierarchical wrinkles is revealed through a simplified theoretical model and validated by experiments. In addition to its tunable optical property, we further show its ability in control of water droplet transport on demand through mechanical stretching and release. We find that an initially pinned water droplet on the tilted hierarchically wrinkled surface starts to slide when the surface is stretched, and becomes pinned again upon strain release. Such a process is reversible and repeatable. The hierarchically wrinkled surface could find broad potential applications not only in multifunctional smart windows with additional features of aesthetics and water collection, but in microfluidics, design of slippery surfaces, and directional water transportation.