Stress has been identified as one of the major causes of automobile crashes which then lead to high rates of fatalities and injuries each year. Stress can be measured via physiological measurements and in this study the focus will be based on the features that can be extracted by common wearable devices. Hence, the study will be mainly focusing on heart rate variability (HRV). This study is aimed at investigating the role of HRV-derived features as stress markers. This is achieved by developing a good predictive model that can accurately classify stress levels from ECG-derived HRV features, obtained from automobile drivers, by testing different machine learning methodologies such as K-Nearest Neighbor (KNN), Support Vector Machines (SVM), Multilayer Perceptron (MLP), Random Forest (RF) and Gradient Boosting (GB). Moreover, the models obtained with highest predictive power will be used as reference for the development of a machine learning model that would be used to classify stress from HRV features derived from heart rate measurements obtained from wearable devices. We demonstrate that HRV features constitute good markers for stress detection as the best machine learning model developed achieved a Recall of 80%. Furthermore, this study indicates that HRV metrics such as the Average of normal-to-normal (NN) intervals (AVNN), Standard deviation of the average NN intervals (SDNN) and the Root mean square differences of successive NN intervals (RMSSD) were important features for stress detection. The proposed method can be also used on all applications in which is important to monitor the stress levels in a non-invasive manner, e.g., in physical rehabilitation, anxiety relief or mental wellbeing.