Condition assessment of insulation is widely used to identify the state of aging of power transformers. Traditionally, condition assessment is done using dielectric response measurements conducted at low frequencies. However, due to long testing time required for these methods, attention has now been paid towards measurements at microwave (above 1 GHz) frequencies. In this paper, we establish a correlation between dielectric properties and the state of aging of transformer pressboard samples. This is useful as it paves way to develop techniques to assess the state of aging by measuring dielectric properties at high frequencies. Dielectric measurements are made by using a microstrip ring resonator. The state of aging is determined by measuring the tensile index. Tests were carried out on dry and wet oil-impregnated pressboard samples thermally aged at laboratory conditions for durations up to 45 days. The results were compared with field aged samples collected from a 33 kV sealed type distribution transformer of 18 years in service. It was found that the permittivity values had a good correlation with respective tensile index values whereas loss tangent values showed limited correlation for both dry and wet samples. The results of field aged samples matched well with the established correlation curves. It can be concluded that the permittivity of pressboard samples estimated from the ring resonator can be effectively used to evaluate the state of aging of transformer insulation.