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ABSTRACT Understanding how the intrinsic ability of populations and species to meet shifting selective demands shapes evolutionary patterns over both short and long timescales is a major question in biology. One major axis of evolutionary flexibility can be measured by phenotypic integration and modularity. The strength, scale, and structure of integration may constrain or catalyze evolution in the face of new selective pressures. We analyze a dataset of seven leaf measurements across Vitaceae to examine how correlations in trait divergence are linked to transitions between freezing and nonfreezing habitats. We assess this by applying a custom algorithm to compare the timing of habitat shifts to changes in the structure of evolutionary trait correlation at discrete points along a phylogeny. We also explore these patterns in relation to lineage diversification rates to understand how and whether patterns in the evolvability of complex multivariate phenotypes are linked to higher‐level macroevolutionary dynamics. We found that shifts in the structure, but not the overall strength, of phylogenetic integration of leaves precipitate colonization of freezing climates. Lineages that underwent associated shifts in leaf trait integration and subsequent movement into freezing habitats also displayed lower turnover and higher net diversification, suggesting a link among shifting vectors of selection, internal constraint, and lineage persistence in the face of changing environments.