(1) Background: There is a need for a novel surrogate marker to ease decision making when facing ascending aortic dilatation. In this article, we study the ratio between ascending and descending aorta diameters as a potential one. (2) Methods: Retrospective observational cohort study, including all the patients who underwent surgery for acute type A aorta dissection (aTAAD) between January 2014 and September 2020 at our center. A total of 50 patients were included. Clinical and demographic data were collected. The anatomical measurements were made including orthogonal maximal diameters of the ascending and descending aorta, post-dissection whole circumference length (post-wCL), post-dissection true lumen circumference length (post-tCL), and surface and sphericity indices of the ascending and descending aorta. Pre-dissection ascending aorta diameter (pre-AAD) and pre-dissection descending aorta diameter (pre-DAD) were calculated as well as the ratio between them and compared with reference values. (3) Results: Of the pre-AAD patients, 96% had smaller than the recommended 55 mm. The ratio between the descending and ascending aorta pre-dissection diameters was significantly smaller compared to the reference value (0.657 ± 0.125 versus 0.745 ± 0.016 with a mean difference of −0.088 and a p < 0.001). (4) Conclusions: The 55 mm threshold for aorta maximal diameter is an insufficient criterion when assessing the risk of dissection. The ratio between DAD and AAD is a parameter worthy of analysis as a tool to stratify the risk of dissection.