Retinal detachment (RD) is a potentially sight-threatening condition that requires timely diagnosis and appropriate surgical management. In macula-off rhegmatogenous retinal detachment (RRD), visual recovery after successful reattachment remains highly variable, underscoring the need for reliable preoperative prognostic markers. This study focuses on the contribution of advanced retinal imaging to the preoperative assessment of macula-off RRD, summarizing current evidence on imaging-derived biomarkers associated with disease severity and postoperative functional outcome. In this review, we analyze studies employing spectral-domain and swept-source optical coherence tomography (SD-OCT and SS-OCT), OCT angiography (OCT-A), and adaptive optics OCT (AO-OCT) to characterize microstructural and microvascular retinal alterations. Emerging approaches, including ultra-widefield OCT (UWF-OCT) and artificial intelligence–based image analysis, are also discussed for their potential role in refining diagnosis, supporting surgical planning, and improving prognostic stratification. While several imaging parameters appear promising, their prognostic value is not yet fully standardized. Further prospective studies are required to validate clinically meaningful imaging biomarkers and to integrate advanced imaging into routine preoperative decision-making for macula-off rhegmatogenous retinal detachment.