Generation 1's art, unlike any other generation, didn't see notable improvement over its six-year span. At this time, the stories and characters didn't have a distinct art style, and largely lent from Jeff Kinney's Diary of a Wimpy Kid series.

Generation 2 was the only generation to feature noticeably different art styles for its stories and art. Notable improvement wasn't seen until 2019, the final year of Generation 2. The styles were as follows:

Generation 3 was the first generation to mostly feature digital, colored art and comics. It's also the generation that started seeing gradual improvement over long periods of time. The aim of the style was to combine, and improve upon, the cartoon and anime styles from Generation 2.

Generation 4's style was revealed to some of Gaboza's close friends, with the debut art of Cleo Duflora being made in February 2024. The new style is similar to, but a noticeable step up from Generation 3. It displays an emphasis on pen pressure.