The living umbrella is resembling of a traditional patio umbrella but with a canopy made of a layer of plants rather than fabric or metal. It is thought to provide comfort and shade to users while increasing nature in hardscaped areas. The study aimed to compare the microclimates of metal canopy umbrella to that of living umbrellas. Metrics used were Wet Bulb Globe Temperature (WBGT), UV transmittance, solar transmittance, air temperature, canopy temperature, and humidity. Compared to ambient conditions, the living umbrella reduced WBGT by 1.5˚C, and UV and solar transmittance by 24.2% and 18%, respectively. The metal umbrella reduced UV and solar transmittance more than the living umbrella, but not WBGT. A second aim was to determine whether there was a Biophilic connection between the living umbrella and its users, which was explored through surveys. The Biophilic connection is exemplified by people who experience feelings of comfort when they are close to nature. The majority of respondents felt strong positive emotions towards the living umbrella, while 81% preferred a living umbrella over a metal umbrella. The research showed that an innovative green technology can improve the microclimate experienced by people while making them feel better.