This study aims to assess whether students’ learning styles have changed due to the environmental context changes caused by the COVID-19 pandemic outbreak. This analysis is important because learning styles, in addition to predicting vocational outcomes, must inform the design of pedagogical practices and supports used in the teaching environment. To achieve this objective, a cross-sectional analysis was conducted on three cohorts of students who enrolled in an engineering course. Students in group 2 have been under confinement conditions during the previous year, while students in group 3 have been under confinement conditions for the previous two years. Group 1 consists of students who did not experience any confinement. The obtained results lead to the following conclusions: (i) The pandemic outbreak has led to environmental changes, pedagogical practices, and changes in the personality profiles of students, which can significantly impact the learning styles of students entering an engineering degree. (ii) While some learning styles are more susceptible to change, others remain resilient. (iii) The duration of exposure to the environmental changes caused by the pandemic outbreak has a greater impact on the changes in these learning styles.