Street trees are important components of an urban green space and understanding and measuring their ecological and cultural services is crucial for assessing the quality of streets and managing urban environments. Currently, most studies mainly focus on evaluating the ecological services of street trees by measuring the amount of greenness, but how to evaluate their aesthetic functions through quantitative measurements of street trees remain unclear. To address this problem, we propose a method to assess the aesthetic functions of street trees by quantifying the shape of greenness inspired by assessments of skyline aesthetics. Using a state-of-the-art mobile mapping system, we collected downtown-wide lidar data and panoramic images in Jinzhou City, Hebei Province, China. We developed a method for extracting the canopy line from the mobile lidar data, and then identified two basic elements, peaks and gaps, from street canopy lines and extracted six indexes (i.e., richness of peaks, evenness of peaks, frequency of peaks, total length of gaps, evenness of gaps and frequency of gaps) to describe the fluctuations and continuities of street canopy lines. We analyzed the abundance and spatial distribution of these indexes together with survey responses on the streets’ aesthetics and found that most of them were significantly correlated with human perception of streets. Compared to indexes of amount of greenness (e.g., green volume and green view index), these shape indexes have stronger influences on the physical aesthetic beauty of street trees. These findings suggest that a comprehensive assessment of the aesthetic function of street trees should consider both shape and amount of greenness. This study provides a new perspective for the assessment of urban green spaces and can assist future urban greening planning and urban landscape management.