We studied the structure of brushes consisting of branched oligolactide (OLA) chains grafted onto the surface of cellulose nanoparticles (CNPs) in polylactide (PLA) and compared the outcomes to the case of grafting linear OLA chains using atomistic molecular dynamics simulations. The systems were considered in a melt state. The branched model OLA chains comprised one branching point and three branches, while the linear OLA chains examined had a molecular weight similar to the branched chains. It was shown that free branches of the branched OLA chains tend to fold back toward the CNPs due to dipole–dipole interactions within the grafted layer, in contrast to the well-established behavior of the grafted uncharged branched chains. This result, however, is in qualitative agreement with the conformational behavior known for linear OLA chains. At the same time, no significant difference in the effectiveness of covering the filler surface with grafted branched or linear OLA chains was found. In terms of the expelling ability of the grafted chains and the interaction between PLA and CNP or OLA, the linear chains were broadly similar (sparse grafting) or better (intermediate or dense grafting) compared to the branched ones. Thus, the grafted lactide chains with a linear architecture, rather than their branched counterpart, may be preferable for the covalent modification of cellulose nanoparticles.