Nutritional monitoring is an important aspect of providing a healthy lifestyle and smarter food consumption. Food recognition is a key task in nutrition monitoring applications especially of interest for older people suffering from malnutrition and unhealthy eating. In order to ease the problem of food intake monitoring, recent health apps involve Artificial Intelligence algorithms for food image analysis. Food recognition is a highly challenging task as the dishes could be composed of mixed types, it could have a lower inter-class variance and also the number of dishes to be recognized is quite higher. In this chapter, we present an in-depth analysis and insights into the development of a nutritional monitoring system that would act as a Key Performance Indicator for the older people food intake monitoring. This system is aimed at providing a convenient food logging environment that would assist older people and their relatives as well as geriatrists in monitoring and maintaining the healthy daily dietary nutritional needs.