Advances in materials science, biomolecule delivery, and cell biology has enabled significant innovations within the field of tissue engineering and regenerative medicine over the past few decades. Nonetheless, minimal translation of tissue engineering-based therapeutics to the clinic has occurred. A significant challenge within tissue engineering is the difficulty in regenerating complex tissues with a heterogeneous structure and multiple cell types. To address this challenge, my research group is developing innovative polymeric biomaterials that can mimic the complex microenvironment of musculoskeletal tissues. Specifically, I will discuss our recent efforts in the following areas: 1) using magnetic fields to spatially control electrospun fiber alignment in order to create materials with gradients in fiber alignment that mimic the structure of musculoskeletal interfacial tissues; 2) using reversible DNA handles to temporally control peptide presentation to improve our understanding of cell-material interactions; and 3) combining these techniques for independent spatial control over chemical and structural signals towards simultaneous regeneration of multiple tissue types.