Recent studies have characterized individually experienced temperatures or individually experienced heat indices, including new exposure metrics that capture dimensions of exposure intensity, frequency, and duration. Yet, few studies have examined the personal thermal exposure in underrepresented groups, like outdoor workers, and even fewer have assessed corresponding changes in physiologic heat strain. The objective of this paper is to examine a cohort of occupationally exposed grounds and public safety workers (n = 25) to characterize their heat exposure and resulting heat strain. In addition, a secondary aim of this work is to compare individually heat index exposure (IHIE) across exposure metrics, fixed-site in situ weather stations, and raster-derived urban heat island (UHI) measurements in Charleston, SC, a humid coastal climate in the Southeastern USA. A Bland-Altman (BA) analysis was used to assess the level of agreement between the personal IHIE measurements and weather-station heat index (HI) and Urban Heat Island (UHI) measurements. Linear mixed-effect models were used to determine the association between individual risk factors and in situ weather station measurements significantly associated with IHIE measurements. Multivariable stepwise Cox proportional hazard modeling was used to identify the individual and workplace factors associated with time to heat strain in workers. We also examined the non-linear association between heat strain and exposure metrics using generalized additive models. We found significant heterogeneity in IHIE measurements across participants. We observed that time to heat strain was positively associated with a higher IHIE, older age, being male, and among Caucasian workers. Important nonlinear associations between heat strain occurrence and the intensity, frequency, and duration of personal heat metrics were observed. Lastly, our analysis found that IHIE measures were significantly similar for weather station HI, although differences were more pronounced for temperature and relative humidity measurements. Conversely, our IHIE findings were much lower than raster-derived UHI measurements. Real-time monitoring can offer important insights about unfolding temperature-health trends and emerging behaviors during thermal extreme events, which have significant potential to provide situational awareness.