Embodiments of the present invention are directed at providing a font similarity system. In one embodiment, a new font is detected on a computing device. In response to the detection of the new font, a pre-computed font list is checked to determine whether the new font is included therein. The pre-computed font list including feature representations, generated independently of the computing device, for corresponding fonts. In response to a determination that the new font is absent from the pre-computed font list, a feature representation for the new font is generated. The generated feature representation capable of being utilized for a similarity analysis of the new font. The feature representation is then stored in a supplemental font list to enable identification of one or more fonts installed on the computing device that are similar to the new font. Other embodiments may be described and/or claimed.