Ocular surface (OS) and dry eye (DE) symptoms are frequent ophthalmic complaints influenced by climate and pollution related with acute and chronic ocular surface symptoms. This study assessed their association with environmental conditions in São Paulo metropolitan area (2016–2020), including air temperature, humidity, atmospheric pressure, ozone (O₃), particulate matter (PM), using IQVIA eye drop sales data and Google search trends. Sympathomimetic decongestant sales correlated with higher temperature (r = 0.434, p = 0.0021), UV radiation (r = 0.643, p < 0.0001), and ozone (r = 0.491, p = 0.0004). Artificial tears and lubricants correlated with ozone (r = 0.452, p = 0.0012) and with searches for “red eye” (r = 0.505, p = 0.0005) and “stye” (r = 0.599, p < 0.0001). To address multicollinearity, Principal Component Analysis (PCA) was applied, with the first two components (PC1 and PC2) explaining 87.3% of variance. Regression models using these components were significant for decongestant sales and “stye” searches. Eye drop sales and search trends thus emerge as potential indicators of OS and DE symptoms, reflecting environmental conditions and informing prevention strategies.