The envisaged de-carbonization of power systems poses unprecedented challenges enhancing the potential of flexible demand. However, the incorporation of the latter in system planning has yet to be comprehensively investigated. This paper proposes a novel planning model that allows co-optimizing the investment and operating costs of conventional generation assets and demand flexibility, in the form of smart-charging/discharging electric vehicles (EV). The model includes a detailed representation of EV operational constraints along with the generation technical characteristics, and accounts for the costs required to enable demand flexibility. Computational tractability is achieved through clustering generation units and EV, which allows massively reducing the number of decision variables and constraints, and avoiding non-linearities. Case studies in the context of the U.K. demonstrate the economic value of EV flexibility in reducing peak demand levels and absorbing wind generation variability, and the dependence of this value on the required enabling cost and users’ traveling patterns.