This book examines the alternation between accusative-dative and dative-accusative order in Old
Florentine clitic clusters and its decline in favor of the latter. Based on an exhaustive
analysis of data collected from medieval Florentine and Tuscan texts we offer a novel analysis
of the rise of the variable order the transition from one order to the other and the demise
of the alternation that relies primarily on iconicity and analogy. The book employs exophoric
pragmatic iconicity a language-external iconic relationship based on similarity between
linguistic structure and the speaker writer's conceptualization of reality and endophoric
iconicity a language-internal iconic relationship where the iconic ground is construed between
linguistic signs and structures. Analogy is viewed as a productive process that generalizes
patterns or extends grammatical rules to formally similar structures and obtains the form of
the analogical relationship between the masculine singular definite article and the third
person singular accusative clitic which shared the same phonotactically constrained
distribution patterns. The data indicate that exophoric pragamatic iconicity exploits and
maintains the alternation whereas endophoric iconicity and analogy conspire to end it.