This paper introduces a little-known print genre that flourished in Britain from the late 1770s to the late nineteenth century. Notwithstanding the long life of the illustrated pocket diary-cum- almanac, scholars have failed to assess the range and variety of these annuals or examine in what ways these print objects were produced in a competitive environment that saw, in its most prolific decades, the publication of up to forty different titles per year. Due to the ephemeral nature of the pocket diaries, very few copies have survived, and some titles known to have existed from advertisements have remained entirely untraced. Yet an attempt at charting this genre’s various contexts of production, marketing, and consumption is rewarding in that it will reveal the richness of these publications in terms of design and layout innovations, the ways in which each of these titles promoted a narrative of cultural literacy, and the increasingly — in the course of the nineteenth century — gender-specific marketing of the titles. While introducing a number of different pocket diaries issued from 1779 to the mid nineteenth century, the essay will discuss the earliest diaries (The Royal Engagement Pocket Atlas, The Polite Repository, and Le Souvenir) in some detail to facilitate an understanding of how the genre developed in the nineteenth century. It will focus, in particular, on these annuals’ illustrative material and the ways in which pocket diaries promoted cultural improvement.