The mass of a star at formation determines its subsequent evolution and demise. Low-mass stars are the most common products of star formation and their long main-sequence lifetimes cause them to accumulate over time. Star formation also produces many substellar-mass objects known as brown dwarfs, which emerge from their natal molecular clouds and continually cool as they age, pervading the Milky Way. Low-mass stars and brown dwarfs exhibit a wide range of physical characteristics and their abundance make them ideal subjects for testing formation and evolution models. I have examined a pair of pre-main sequence spectroscopic binaries and used radial velocity variations to determine orbital solutions and mass ratios. Additionally, I have employed synthetic spectra to estimate their effective temperatures and place them on theoretical Hertzsprung-Russell diagrams. From this analysis I discuss the formation and evolution of young binary systems and place bounds on absolute masses and radii. I have also studied the late-type T dwarfs revealed by the Wide-field Infrared Survey Explorer (WISE). This includes the exemplar T8 subdwarf Wolf 1130C, which has the lowest inferred metallicity in the literature and spectroscopic traits consistent with old age. Comparison to synthetic spectra implies that the dispersion in near-infrared colors of late-type T dwarfs is a result of age and/or thin sul de clouds. With the updated census of the L, T, and Y dwarfs we can now study specific brown dwarf subpopulations. Finally, I present a number of future studies that would develop our understanding of the physical qualities of T dwarf color outliers and disentangle the tracers of age and atmospheric properties. The thesis is available at: http://www.astro.ucla.edu/~gmace/thesis.html