Divergent understandings of hadith regarding the hijab in the thought of Yūsuf al-Qaraḍāwī and Muḥammad Saʿīd al-ʿAshmāwī reveal methodological issues in the relationship between hadith authority, Qur’anic interpretation, socio-historical context, legal reasoning, and determining the scope of dress norms for women. It is insufficient to characterize the difference between them merely as an ideological conflict, as each scholar’s argument involves choices about sources, normative assumptions, and procedures for linking texts to legal rulings. This study aims to analyze the methods of hadith understanding employed by both figures, identify their similarities and differences, and explain the sources of their divergent arguments regarding the hijab. Using a comparative-qualitative design, this library-based research applies textual-hermeneutic analysis to the relevant works of both figures, with the hadith as the basis for their arguments, alongside pertinent Qur’anic verses and verifiable academic literature. The analysis reveals similarities in using Qur’anic verses as a foundation for discussion and in the attention paid to the relationship between text, meaning, and context. Key differences lie in the weight accorded to hadith authority, the function of historical reconstruction, and the basis for generalizing norms. Al-Qaraḍāwī integrates hadith with the Qur’an, synthesizes relevant narrations, and considers scholarly explanations to distinguish the obligation to cover the hair from the obligation to cover the face. Al-ʿAshmāwī places greater emphasis on the historical context of verses and hadith, while criticizing the establishment of universal obligations based on āḥād (solitary) narrations. This comparison highlights divergent conclusions rooted in differing approaches to evaluating evidence and linking context to norms, without demonstrating the absolute superiority of either approach.