We use the Wide Field Camera 3 (WFC3) onboard the Hubble Space Telescope (HST) to obtain deep, high resolution images of two intermediate-age star clusters in the Large Magellanic Cloud of relatively low mass ($approx$ $10^4$ $M_{odot}$) and significantly different core radii, namely NGC2209 and NGC2249. For comparison purposes, we also re-analyzed archival HST images of NGC1795 and IC2146, two other relatively low mass star clusters. From the comparison of the observed color-magnitude diagrams with Monte Carlo simulations, we find that the main sequence turnoff (MSTO) regions in NGC2209 and NGC2249 are significantly wider than that derived from simulations of simple stellar populations, while those in NGC1795 and IC2146 are not. We determine the evolution of the clusters masses and escape velocities from an age of 10 Myr to the present age. We find that the differences among these clusters can be explained by dynamical evolution arguments if the currently extended clusters (NGC2209 and IC2146) experienced stronger levels of initial mass segregation than the currently compact ones (NGC2249 and NGC1795). Under this assumption, we find that NGC2209 and NGC2249 have estimated escape velocities $V_{rm esc}$ $geq$ 15 km s$^{-1}$ at an age of 10 Myr, large enough to retain material ejected by slow winds of first-generation stars, while the two clusters that do not feature extended MSTOs have $V_{rm esc}$ $leq$ 12 km s$^{-1}$ at that age. These results suggest that the extended MSTO phenomenon can be better explained by a range of stellar ages rather than a range of stellar rotation velocities or interacting binaries.