In the pursuit of sustainability and reduced dependence on new plastic materials, this study explores the upcycling potential of high-density polyethylene (HDPE) milk bottles into high-stiffness, high-heat-distortion-temperature (HDT) composites. Recycled high-density polyethylene (rHDPE) sourced from used milk bottles serves as the composite matrix, while reinforcing fillers are derived from dried pineapple leaves, comprising fibers (PALF) and non-fibrous materials (NFM). A two-roll mixer is employed to prepare rHDPE/NFM and rHDPE/PALF mixtures, facilitating filler alignment in the resulting prepreg. The prepreg is subsequently stacked and pressed into composite sheets. The introduction of PALF as a reinforcing filler significantly enhances the flexural strength and modulus of the rHDPE composite. A 20 wt.% PALF content yields a remarkable 162% increase in flexural strength and a 204% increase in modulus compared to neat rHDPE. The rHDPE/NFM composite also shows improved mechanical properties, albeit to a lesser degree than fiber reinforcement. Both composites exhibit a slight reduction in impact resistance. Notably, the addition of NFM or PALF substantially elevates HDT, raising the HDT values of the composites to approximately 84 °C and 108 °C, respectively, in contrast to the 71 °C HDT of neat rHDPE. Furthermore, the overall properties of both the composites are further enhanced by improving their compatibility through maleic anhydride-modified polyethylene (MAPE) use. Impact fracture surfaces of both composites reveal higher compatibility and clear alignment of NFM and PALF fillers, underscoring the enhanced performance and environmental friendliness of composites produced from recycled plastics reinforced with pineapple leaf waste fillers.