A pylon assembly for a tiltrotor aircraft includes a rotor assembly rotatably coupled to a fixed pylon and operable to rotate between a vertical takeoff and landing orientation and a forward flight orientation. The rotor assembly includes a proprotor operable to produce a slipstream. A wing extension is rotatably disposed to the outboard end of the fixed pylon such that the rotor assembly and the wing extension are separated by at least a portion of the fixed pylon. The wing extension has a forward edge and an outboard end. A winglet is coupled to the outboard end of the wing extension and has a forward edge. The wing extension and the winglet are configured to rotate in synchrony with the rotor assembly such that the forward edges of the wing extension and the winglet remain in the slipstream of the proprotor.