In this pandemic time, wearing face masks is mandatory to all because of the possibility that a person can get COVID-19 virus through their mouth, nose or eyes, which could possibly happen when a person has a direct or close contact to a person with that virus. But, despite the strict implementation, some people disregard the proper wearing of face masks and unaware the risks of possible virus transmission for such negligence. In this paper, it will demonstrate how a Convolutional Neural Network (CNN) can detect if a person is wearing a face mask or not and the additional parameter to support to detect if the face mask is properly worn by a person by considering the facial landmarks thru face recognition using Histogram of Oriented Gradients (HOG) feature descriptor with a linear SVM machine learning algorithm. Two (2) processes are involved in proper wearing of face masks detection. It needs to pass in Face Mask Detection to proceed to the next process which is the Face detection wherein the result of checking should return false to confirm the proper wearing of the face mask of a person.