This study investigates the translation of similes in two Arabic versions of Ernest Hemingway’s Men Without Women, translated by Abdullah Fadhel Farea (2007) and Sameer Izzat Nassar (2003). Focusing on the cultural and stylistic importance of similes in Hemingway’s work, it examines the translation techniques used by each translator and evaluates their success in bridging linguistic and cultural differences. Using Katharina Reiss’s functional model (2000), the analysis assesses how semantic, lexical, and stylistic elements affect the translation of similes. It examines strategies like figurative equivalence, literal translation, and adaptation, highlighting both successful and problematic examples. The study reveals that while both translators aim to preserve Hemingway’s vivid imagery, their approaches to cultural nuances differ. The findings emphasize the importance of considering cultural context and audience expectations when translating similes to ensure both fidelity to the original text and resonance with the target readership.