This thesis is an exploration of the process of getting dressed, and how it is incredibly complex. This paper identifies the multiple variables that go into the decisions and motives people have when styling a complete outfit. These variables will be explored through my expertise of being a personal stylist and shopper, and with expert consultations in different technology fields. The purpose of the What Do I Wear? mobile application is to assist people getting dressed by recommending an outfit that suits the users body shape, activity, represents their personal style, and is suitable for the weather. The final product is a mobile application that functions as a personal stylist, utilizing an artificial intelligence agent trained on using identified variables when styling an outfit.