As the population of older adults increases, so does the demand for technology that supports caregiving and aging in place. Smart home technology, wearable health trackers, and mobile applications have all been identified as possible methods of support. Studies on the user interfaces of these technologies have predominantly explored how well their features and functions address the complex needs of older adults and caregivers. However, many of these applications lack adequate consideration of visual design principles and aesthetics. The present study aims to illustrate the iterative design process of the LifeTomorrow Ecosystem which includes two applications: one for caregivers and one for older adult care recipients. The results include high-fidelity screens from the applications that incorporate functional and visual design principles, as well as the feedback of older adults, caregivers, and designers. Finally, we provide recommendations for designers to consider when designing applications targeted at older adults and their caregivers.