Size estimation is a hard computer vision problem with widespread applications in quality control in manufacturing and processing plants, livestock management, and studies on animal behaviour. Typically, image-based size estimation is facilitated by either well-controlled imaging conditions, the provision of global cues, or both. Reference-free size estimation is challenging, because objects of vastly different sizes can appear identical if they are of similar shape. Here, we attempt to implement automated and reference-free body size estimation to facilitate large-scale experimental work in a key model species in sociobiology: the leaf-cutter ants. Leaf-cutter ants are a suitable testbed for reference-free size-estimation, because their workers differ vastly in both size and shape; in principle, it is therefore possible to infer body mass, a proxy for size, from relative body proportions alone. Inspired by earlier work by E.O. Wilson, who trained himself to discern ant worker size from visual cues alone, we used various deep learning techniques to achieve the same feat automatically, quickly, and at scale from a single reference image: Wilson Only Looks Once (WOLO). Utilizing over 3 million hand-annotated and computer-generated images, a set of deep neural networks including regressors, classifiers, and detectors were trained to estimate the body mass of ants from image cut-outs. The WOLO networks approximately matched human performance, measured for a small group of both experts and non-experts, but were about 1000 times faster. Further refinement may enable accurate, high-throughput, and non-intrusive body weight estimation at scale, and so eventually contribute to a more nuanced and comprehensive understanding of the complex division of labour that characterises polymorphic insect societies.