At commencement you wear your square-shaped mortarboards. My hope is that from time to time you will let your minds be bold, and wear sombreros.

Freund contrasts the conventional mortarboard—symbol of formal education, conformity, and credentialing—with the sombrero, a playful emblem of breadth, flair, and nonconformity. The image suggests that graduation should not mark the end of intellectual risk-taking; rather, the habits of mind cultivated in school should be periodically “worn” in bolder forms: questioning assumptions, entertaining unorthodox ideas, and approaching problems with imaginative range. Coming from a prominent legal scholar, the line also reads as advice to professionals: technical competence and respect for rules matter, but so do creativity, moral courage, and the willingness to see beyond established frameworks.