The development of ultra-thin dielectrics for low power electronics operations, flexible and printed electronics, and field effect transistors based sensors is still a challenge. Here monolayers of engineered lipids supported on silicon are reported presenting exceptional mechanical and dielectric properties. The lipid monolayers are stabilized using a simple procedure based on a two-stage reticulation process in both their aliphatic chains and their head-group. With a 2 thickness lower than 3 nm, such layers are demonstrated to offer exceptional mechanical and dielectric stability with unprecedented low leakage current and dielectric strength. Surprisingly, the mechanical and dielectric pressures required to rupture/breakdown the monolayers are shown to be similar. These results suggest the presence of a strong correlation between mechanical and dielectric properties, as well as between the mechanisms of rupture and breakdown.