Current imaging systems available in the study of tissue hemodynamics and vascular reactivity are typically complex and bulky, hence limiting their applications to laboratory use. The aim of this study is to present the dynamics of skin oxygen level with changes in the microcirculatory perfusion monitored using a developed field portable, handheld tri-wavelength imaging system. The skin oxygen saturation level (StO2) was measured in-vivo in a span of 12 minutes in the ventral forearm of seven healthy humans at rest, before and after supra-diastolic and supra-systolic pressure inflations. The findings of this work showed statistical significance in the difference between the mean StO2 values in baseline and that following ischemic episodes with ρ ≤ 0.03. The values returned to baseline, although of different magnitude for each individual, within 2 min (ρ =0.217) during reperfusion could suggest the time required for the resume of normal autoregulation mechanisms and vasomotion reactivities in the recruits. This study concluded that the developed imaging system could find potential application in self-healthcare management and may help to improve patient care in remote or rural locations.