Natural rubber (NR), derived from Hevea brasiliensis, is an important biopolymer known for its elasticity, resilience, and tensile strength. Their properties can be substantially improved with the addition of biopolymeric fillers like chitin and chitosan whiskers, which are getting immense scientific and commercial attention because of their biocompatibility, biodegradability, and excellent mechanical properties. Chitin is a structural component of crustacean shells, with chitosan being its derivative; chitin and chitosan exhibit high crystallinity and mechanical strength and are thus used as reinforcements in rubber composites. This study explores the methods to incorporate chitin and chitosan whiskers in a natural and synthetic rubber matrix through solution casting, latex stage blending, and two-roll mill mixing. Studies show that these composites thus exhibit improved mechanical, thermal, and barrier properties due to the strong interface interaction and network structure of the whiskers with the rubber matrix, and such properties can be characterized using techniques like dynamic mechanical analysis, thermogravimetric analysis, and scanning electron microscopy that were employed to assess the structural and mechanical improvement of these composites. Here, we discussed the broader industrial, biomedical, environmental, and agronomic applications of these biocomposite materials, in regard to their performance as sustainable and green alternatives to the conventional rubber formulations. This chapter highlights the ability of chitin and chitosan whiskers to enhance rubber-based materials, stressing their contribution toward the evolution of high-performance, biodegradable, and eco-friendly composites.