Studies of anatomically preserved fossils provide a wealth of information on the evolution of plant vascular systems through time, from the oldest evidence of vascular plants more than 400 million years ago to the rise of the modern angiosperm-dominated flora. In reviewing the key contributions of the fossil record, we discuss knowledge gaps and major outstanding questions about the processes attending the evolution of vascular systems. The appearance and diversification of early vascular plants in the late Silurian-Devonian was accompanied by the evolution of different types of tracheids, which initially improved the hydraulics of conduction but had less of an effect on mechanical support. This was followed in the Devonian and Carboniferous by an increase in complexity of the organization of primary vascular tissues, with different types of steles evolving in response to mechanical, hydraulic, and developmental regulatory constraints. Concurrently, secondary vascular tissues, such as wood, produced by unifacial or bifacial cambia are documented in a wide array of plant groups, including some that do not undergo secondary growth today. While wood production has traditionally been thought to have evolved independently in different lineages, accumulating evidence suggests that this taxonomic breadth reflects mosaic deployment of basic developmental mechanisms, some of which are derived by common ancestry. For most of vascular plant history, wood contained a single type of conducting element: tracheids (homoxyly). However, quantitative (e.g. diameter and length) and qualitative (e.g. pitting type) diversity of these tracheids allowed various taxa to cover a broad range of hydraulic properties. A second type of conducting elements, vessels, is first documented in an extinct late Permian (c. 260 Ma) group. While the putative hydraulic advantages of vessels are still debated, wood characterized by presence of vessels (heteroxyly) would become the dominant type, following the diversification of angiosperms during the Cretaceous.