This article provides a jurisprudential-legal assessment of Iran's "Law on Supporting the Family through the Promotion of the Culture of Chastity and Hijab," examining it against foundational principles of Imamiyya jurisprudence. Using a comparative-analytical approach, the study evaluates key maxims—including human dignity, divine sovereignty, otherworldly interests, expediency, freedom, presumption of innocence, tolerance, no-harm, and prohibition of hardship—against the law's specific provisions. The findings indicate that at the macro-theoretical level, the law aligns with Islamic jurisprudence, particularly in its objectives of safeguarding public modesty and moral security. However, significant contradictions emerge in enforcement mechanisms. The law violates the presumption of innocence through automatic fines and eliminated due process, undermines tolerance by prescribing fourth-degree imprisonment, disregards the no-harm principle by inflicting damages on innocents, and breaches the hardship prohibition. The article concludes that reforming the law by abolishing automatic penalties, restoring fair judicial procedures, and prioritizing cultural-educational measures is essential. Without such amendments, despite its theological legitimacy, the law risks losing social acceptance and practical effectiveness.