Infrared optical investigations of $alpha$-(BEDT-TTF)$_2$I$_3$ have been performed in the spectral range from 80 to 8000~cm$^{-1}$ down to temperatures as low as 10~K by applying hydrostatic pressure. In the metallic state, $T > 135$~K, we observe a 50% increase in the Drude contribution as well as the mid-infrared band due to the growing intermolecular orbital overlap with pressure up to 11~kbar. In the ordered state, $T<T_{rm CO}$, we extract how the electronic charge per molecule varies with temperature and pressure: Transport and optical studies demonstrate that charge order and metal-insulator transition coincide and consistently yield a linear decrease of the transition temperature $T_{rm CO}$ by $8-9$~K/kbar. The charge disproportionation $Deltarho$ diminishes by $0.017~e$/kbar and the optical gap $Delta$ between the bands decreases with pressure by -47~cm$^{-1}$/kbar. In our high-pressure and low-temperature experiments, we do observe contributions from the massive charge carriers as well as from massless Dirac electrons to the low-frequency optical conductivity, however, without being able to disentangle them unambiguously.
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