Out-of-office blood pressure (BP) measurement is considered an integral component of the diagnostic algorithm and management of hypertension. In the era of digitalization, a great deal of wearable BP measuring devices has been developed. These digital blood pressure monitors allow frequent BP measurements with minimal annoyance to the patient while they do promise radical changes regarding the diagnostic accuracy, as the importance of making an accurate diagnosis of hypertension has become evident. By increasing the number of BP measurements in different conditions, these monitors allow accurate identification of different clinical phenotypes, such as masked hypertension and pathological BP variability, that seem to have a negative impact on cardiovascular prognosis. Frequent measurements of BP and the incorporation of new features in BP variability, both enable well-rounded interpretation of BP data in the context of real-life settings. This article is a review of all different technologies and wearable BP monitoring devices.