We describe the design, algorithm, implementation and experiments with ClosetStylist – an Android app that helps users digitize their clothing inventory for better usage, manage outfit worn history, laundry bags, and last but not least, suggest what to wear based on occasion and weather. The app utilizes a variety of off-the-shelf services such as location and weather services, combining with our own clothes matching algorithm to recommend the most suitable outfit to users. In addition to the main features, ClosetStylist offers a friendly user interface that enables smooth navigation and keeps users engaged. The app was tested under different mock weather conditions with two sets of wardrobe, specifically a male closet of 24 items and a female closet of 86 items. The recommended outfits were displayed on the screen within three seconds of the moment the user initiated the options from the main menu. The app recommended satisfying results which we would hand-pick as our daily outfits. / text