The availability of wearable devices (WDs) to collect biometric information and their use during activities of daily living is significantly increasing in the general population. These small electronic devices, which record fitness and health-related outcomes, have been broadly utilized in industries such as medicine, healthcare, and fitness. Since they are simple to use and progressively cheaper, they have also been used for numerous research purposes. However, despite their increasing popularity, most of these WDs do not accurately measure the proclaimed outcomes. In fact, research is equivocal about whether they are valid and reliable methods to specifically evaluate physical activity and health-related outcomes in older adults, since they are mostly designed and produced considering younger subjects’ physical and mental characteristics. Additionally, their constant evolution through continuous upgrades and redesigned versions, suggests the need for constant up-to-date reviews and research. Accordingly, this article aims to scrutinize the state-of-the-art scientific evidence about the usefulness of WDs, specifically on older adults, to monitor physical activity and health-related outcomes. This critical review not only aims to inform older consumers but also aid researchers in study design when selecting physical activity and healthcare monitoring devices for elderly people.