Many details about our world are not captured in written records because they are too mundane or too abstract to describe in words. Fortunately, since the invention of the camera, an ever-increasing number of photographs capture much of this otherwise lost information. This plethora of artifacts documenting our "visual culture" is a treasure trove of knowledge as yet untapped by historians. We present a dataset of 37,921 frontal-facing American high school yearbook photos that allow us to use computation to glimpse into the historical visual record too voluminous to be evaluated manually. The collected portraits provide a constant visual frame of reference with varying content. We can therefore use them to consider issues such as a decade's defining style elements, or trends in fashion and social norms over time. We demonstrate that our historical image dataset may be used together with weakly-supervised data-driven techniques to perform scalable historical analysis of large image corpora with minimal human effort, much in the same way that large text corpora together with natural language processing revolutionized historians' workflow. Furthermore, we demonstrate the use of our dataset in dating grayscale portraits using deep learning methods. Click to Read Paper