The squeezing dynamics of a damped harmonic oscillator are studied for different types of environment without making the Markovian approximation. The squeezing dynamics of a coherent state depend on the reservoir spectrum in a unique way that can, in the weak coupling approximation, be analyzed analytically. Comparison of squeezing dynamics for Ohmic, sub-Ohmic and super-Ohmic environments is done showing a clear connection between the squeezing--non-squeezing oscillations and reservoir structure. Understanding the effects occurring due to structured reservoirs is important both from a purely theoretical point of view and in connection with evolving experimental techniques and future quantum computing applications.