The film contains no depictions of non-cisnormative identities or same-sex intimacy. Narrative dynamics focus on heteronormative courtship, particularly during the competition for a female protagonist in the Sleepy Hollow segment.

Gender hierarchies are reinforced through traditional roles. Katrina Van Tassel serves as a romantic prize, while the Wind in the Willows segment features an all-male cast that centers a masculine social sphere.

The cast is homogeneous, reflecting the English countryside and rural New York settings. There is a lack of intersectional presence or non-Anglo-Saxon characters within the narrative.

The film leans into traditional Western social structures and values. While it touches on class through Mr. Toad's consumerism, it lacks a systemic critique of institutional power or capitalism.

There is no meaningful representation of neurodivergence or physical disability. Ichabod Crane’s awkwardness and fear are used as comedic tropes rather than nuanced character studies.