Summary Among flowering plants, self‐compatibility, longer lifespan, and generalized pollination syndrome are each thought to increase the lifetime odds of finding a mate, particularly in isolated locales. An accumulated body of evidence supports the role of breeding system in island colonization, but less is known about the impact of other traits and their interactions during establishment. We employ a global dataset of 3222 flowering plant species from 169 families to estimate the effects of traits on the probability of island occurrence. Our analyses additionally account for taxonomic group membership and assess the role of island arrival opportunity. Self‐compatibility is strongly associated with island colonization. A longer lifespan and generalized pollination syndrome are also associated with increased island colonization, although this is influenced by their interaction with breeding system. The probability of island colonization is highly dependent on taxonomically conserved unmeasured traits and arrival opportunity. As expected, mate limitation appears to increase with dispersal distance, although many other factors are at play. We find that arrival opportunity and breeding system are the primary drivers of island colonization relative to other life‐history traits we account for here, lending additional support for the positive role of uniparental reproduction in establishment following long‐distance dispersal.