The study explored ways in which briefs can be structured to support creative design outcomes. The procedure involved a controlled, yet analytical experiment carried out in a university setting to test the use of analogical reasoning under different conditions to enhance the creativity of design solutions. The first goal was to verify whether visual and text analogies contribute to enhancing design creativity, measured by novel and useful solutions. The second goal was to explore the use of visual and text analogies in creative designs when instructions to formulate negative statements about the problem were provided. A final goal was to test whether correlations exist between the students’ self-reported creativity and their design outcomes scores. 179 first-year undergraduate students participated in this study. The results showed that design briefs with specific instructions to use text or visual analogies yielded highly novel outcomes. However, when text or visual analogies were triggered by statements concerning negative issues of the design problem, more useful outcomes were produced. Moreover, significant relationships were found between self-perceived creativity and the novelty of the outcomes generated in the visual and text analogy briefs. It is suggested that both types of analogies should be employed as effective design studio pedagogical tools to enhance creativity. Negative statements should be considered when the design goal is to improve existing features of current solutions.