Nanosized drug delivery systems (NDDSs) have emerged as a powerful tool to optimize drug delivery in complex diseases, including cancer and inflammation. However, the therapeutic effect of NDDSs is still far from satisfactory due to their poor circulation time, low delivery efficiency, and innate toxicity. Fortunately, biomimetic approaches offer new opportunities to develop nanomedicine, which is derived from a variety of native biomolecules including cells, exosomes, bacteria, and so on. Since inheriting the superior biocompatibility and versatile functions of natural materials, biomimetic nanomedicine can mimic biological processes, prolong blood circulation, and lower immunogenicity, serving as a desired platform for precise drug delivery for treating cancer and inflammatory disease. In this review, we outline recent advances in biomimetic NDDSs, which consist of two concepts: biomimetic exterior camouflage and bioidentical molecule construction. We summarize engineering strategies that further functionalized current biomimetic NDDSs. A series of functional biomimetic NDDSs created by our group are introduced. We conclude with an outlook on remaining challenges and possible directions for biomimetic NDDSs. We hope that better technologies can be inspired and invented to advance drug delivery systems for cancer and inflammation therapy.