Schur polynomials are special cases of Schubert polynomials, which in turn are special cases of dual characters of flagged Weyl modules. The principal specialization of Schur and Schubert polynomials has a long history, with Macdonald famously expressing the principal specialization of any Schubert polynomial in terms of reduced words. We study the principal specialization of dual characters of flagged Weyl~modules. Our result yields an alternative proof of a conjecture of Stanley about the principal specialization of Schubert polynomials, originally proved by Weigandt.