In today’s ever changing world, it is very important to keep a holistic track of a user’s needs and wants. Maslow proposed that human needs can be organized into a hierarchy that ranges from base level needs such as food and water to top tier concepts such as self-fulfillment . The notions of self fulfilment emerge from the emotional comfort that a user experiences whenever he/she interacts with any product or situation. Hence, a specialized understanding of various emotions and their effects is required. This brings us to a form of complicated human emotion that we have often elicited and experienced in our life. The emotion of ‘kawaii’ or ‘cute’ or the ‘Aww emotion.’ This study focuses on the kawaiiness of various design trends followed by different websites or graphical user interfaces (GUIs). It aims to evaluate the kawaii features that enhance or diminish the approachability and attractiveness of different web-based interfaces through self-devised experimentation and analysis. The results show clear notions of ‘kawaiiness’ in certain design trends that use pastel colors and softer animations. At the same time, evident characteristics for ‘not kawaii’ websites that used darker and bolder colors along with real images were also found.