Stars are involved in most research fields of astronomy, ranging from studies of faraway galaxies, exploding supernovae, to more nearby exoplanets and even our own Sun. As such, it is paramount that our physical interpretation of stars is accurate. By observing stars at different epochs, we can fashion evolutionary models to predict important events that occur at different phases during their life-cycle. Thus, exemplary stars where properties including mass, age and luminosity can be observed become increasingly valuable as benchmarks for calibrating said models with. Sometimes, all of these essential properties can be measured for a single system. For instance, for a binary star which circles a common centre of mass we can from its orbital motion calculate the dynamical mass of the system. If the stellar system also has a well-determined age we may use it as a benchmark for our models, and hence refer to it as an emblematic binary system.

In this thesis we are searching for exactly these emblematic binaries, both among lowmass stars and substellar brown dwarfs. We also show how to measure the different characteristics that make the systems into exemplary touchstones. We provide an overview over the different types of stellar binaries, how mass and age estimates are performed, as well as discuss the implications multiplicity has for the formation and evolution of stars and brown dwarfs. In Paper I we present the results from an orbital fit we constrained for a low-mass binary with a known age, making into a valuable and relatively rare benchmark. We also show in Paper II how long baseline astrometry can be exploited in order to place better constraints for orbital fits and dynamical masses for low-mass companions to stars by measuring the perturbation in proper motion over time. The dynamical masses are sequentially tested against evolutionary models, which at these low masses display several discrepancies compared to the observables, and are thus questioned. We explore more uncharted mass-regimes in Paper III, where we employ laser guide star assisted adaptive optics to search for multiplicity among faint substellar objects in young moving groups, detecting 3 new young brown dwarf binary systems. These new binaries will prove to be highly valuable systems for future research of brown dwarfs, and will be able to be studied further with for instance the Extremely Large Telescope or James Webb Space Telescope, which also makes them into prominent benchmarks for substellar evolutionary models. Furthermore, age estimation typically dominates the error budget for low-mass stars and brown dwarfs, requiring several different approaches for a robust assessment. In Paper IV we test and compare different techniques for age determination of 7 low-mass binary stars. These binaries have had their orbital motion monitored for a longer time, and will soon be constrained well enough that dynamical masses may be procured. As such, these low-mass binaries will extend the so far scarce number of exemplary systems where both mass, luminosity and age can be determined, to later be used to calibrate theoretical evolutionary models.