Sunshades are widely used to alleviate outdoor heat stress, yet conventional parasols often block airflow and trap heat, limiting their cooling performance. This chapter introduces an innovative “fanned parasol,” which integrates a lightweight canopy with a compact fan to provide enhanced relief from thermal discomfort. The device is portable, affordable, and designed for practical outdoor use. Field experiments demonstrated that the cooling benefit of the fanned parasol is more pronounced in the initial stage of operation, when stored cooling energy within the canopy is most active. Compared with a traditional parasol, the fanned version strengthens thermal relief through both direct airflow and indirect cooling effects, effectively counteracting the drawbacks of airflow obstruction. Quantitatively, the indirect fan effect was identified as the dominant mechanism, contributing more than 60% of the overall enhancement in both operational stages. These findings highlight the potential of the fanned parasol as a practical strategy for mitigating outdoor heat stress and improving thermal comfort in hot urban environments.