The existence of charged Higgs boson(s) is inevitable in models with two (or more) Higgs doublets. Hence, their discovery would constitute unambiguous evidence for new physics beyond the Standard Model (SM). Taking into account all relevant results from direct charged and neutral Higgs boson searches at LEP and the LHC, as well as the most recent constraints from flavour physics, we present a detailed analysis of the current phenomenological status of the charged Higgs sector in a variety of wellmotivated two Higgs doublet models (2HDMs). We find that charged Higgs bosons as light as 75 GeV can still be compatible with the combined data, although this implies severely suppressed charged Higgs couplings to all fermions. In more popular models, e.g. the 2HDM of Type II, we find that flavour physics observables impose a combined lower limit on the charged Higgs mass of M H ± 600 GeV -independent of tan β -which increases to M H ± 650 GeV for tan β < 1. We furthermore find that in certain scenarios, the signature of a charged Higgs boson decaying into a lighter neutral Higgs boson and a W boson provides a promising experimental avenue that would greatly complement the existing LHC search programme for charged Higgs boson(s).