This article presents data from detailed analyses of the Initial Upper Palaeolithic personal ornaments and formal bone tools excavated from the East Chamber of Denisova Cave. The bone tools include an eyed needle and an awl made from tubular bones of large mammals. The personal ornaments include flat and volumetric beads, pendants, plaques, rings, a button/fastener, decorated bone and bracelet. They show that the Palaeolithic inhabitants of Denisova Cave used a variety of raw materials for making ornaments, including mammal teeth, mammoth ivory, ostrich eggshell, tubular bones from animals and birds, as well as different types of soft stone. Data from technological and experimental use-wear analyses elucidate long and short production sequences or chaîne opératoire, used in ornament manufacture. Micro-wear examination of the artefact surfaces reveals evidence indicating the different ways in which the ornaments were used. Microscopic observations also revealed traces of red ocher pigment on the personal ornaments. This evidence of pigment usage from Denisova Cave is the oldest known in the context of symbolic behavior in the deep history of Northern and Central Asia.