The present study examined students' first impressions of different aesthetic treatments for the same web-based lesson about the experiences of British soldiers during World War I as expressed through examples of trench poetry. Holding site content and functionality constant, the interface design's visual presentation was manipulated along two dimensions: (1) Design Positioning, examined with respect to Aesthetic Value (Good, Poor) and Gender Orientation (Masculine, Feminine, Neutral) and (2) Design Novelty (Contemporary, Dated, Outdated). This resulted in 15 different visual presentations of the online lesson. All students rated each design with respect to appeal. They also indicated the design they most preferred for further engagement with the web-based lesson. Ratings of appeal for the different design styles were examined with respect to the learning topic as well as learners' gender, interest in, and perceived knowledge about: history, World War I, poetry, web design, and online learning. Results regarding students' visual preferences and issues surrounding the influences of the learning context are discussed. (Contains 4 tables and 5 figures.)