Background and objectives: Exertional heat stroke (EHS) is a potentially lethal, hyperthermic condition that warrants immediate cooling to optimize the patient outcome. The study aimed to examine if a portable cooling vest meets the established cooling criteria (0.15 °C·min−1 or greater) for EHS treatment. It was hypothesized that a cooling vest will not meet the established cooling criteria for EHS treatment. Materials and Methods: Fourteen recreationally active participants (mean ± SD; male, n = 8; age, 25 ± 4 years; body mass, 86.7 ± 10.5 kg; body fat, 16.5 ± 5.2%; body surface area, 2.06 ± 0.15 m2. female, n = 6; 22 ± 2 years; 61.3 ± 6.7 kg; 22.8 ± 4.4%; 1.66 ± 0.11 m2) exercised on a motorized treadmill in a hot climatic chamber (ambient temperature 39.8 ± 1.9 °C, relative humidity 37.4 ± 6.9%) until they reached rectal temperature (TRE) >39 °C (mean TRE, 39.59 ± 0.38 °C). Following exercise, participants were cooled using either a cooling vest (VEST) or passive rest (PASS) in the climatic chamber until TRE reached 38.25 °C. Trials were assigned using randomized, counter-balanced crossover design. Results: There was a main effect of cooling modality type on cooling rates (F[1, 24] = 10.46, p < 0.01, η2p = 0.30), with a greater cooling rate observed in VEST (0.06 ± 0.02 °C·min−1) than PASS (0.04 ± 0.01 °C·min−1) (MD = 0.02, 95% CI = [0.01, 0.03]). There were also main effects of sex (F[1, 24] = 5.97, p = 0.02, η2p = 0.20) and cooling modality type (F[1, 24] = 4.38, p = 0.047, η2p = 0.15) on cooling duration, with a faster cooling time in female (26.9 min) than male participants (42.2 min) (MD = 15.3 min, 95% CI = [2.4, 28.2]) and faster cooling duration in VEST than PASS (MD = 13.1 min, 95% CI = [0.2, 26.0]). An increased body mass was associated with a decreased cooling rate in PASS (r = −0.580, p = 0.03); however, this association was not significant in vest (r = −0.252, p = 0.39). Conclusions: Although VEST exhibited a greater cooling capacity than PASS, VEST was far below an acceptable cooling rate for EHS treatment. VEST should not replace immediate whole-body cold-water immersion when EHS is suspected.