The introduction of diverse dynamic bonds into the polysiloxane crosslinked networks can form dynamic crosslinked silicones and their composites, which not only maintain the good physicochemical performance of polysiloxane, but also exhibit novel self-healability and reprocessability. They have shown broad application prospects in smart coatings, sensors and flexible devices. However, the trade-off between excellent dynamic behavior and high mechanical property is challenging their practical applications. To improve this situation, recent advances that highlight the molecular structure design, property modulation and potential application of dynamic crosslinked silicones and their composites with self-healing and reprocessing abilities are reviewed herein. Firstly, self-healing silicones are discussed according to their dynamic crosslinked network that is transforming from single dynamic bond to multiple dynamic bonds to optimize mechanical property and self-healing efficiency. Next, the recycling or reprocessing of dynamic crosslinked silicones are also reviewed in accordance with their reprocessing methods to meet special requirements from different fields. Then, dynamic crosslinked silicone composites are discussed in terms of kinds of nanofillers to further enhance properties and broaden functionalities. What is more, the promising prospects and facing challenges of dynamic crosslinked silicones and their composites are also proposed to achieve an early realization of commercial applications.