In this work, we show that a combined approach of chemistry, characterization, and simulation can provide insight into the structure of bottlebrushes over a wide range of molecular parameters. We consider the specific chemistry of poly(norbornene) (PNB) backbones with poly(lactic acid) (PLA) side chains, so that we can exercise precise synthetic control over backbone and side-chain lengths. We subsequently focus on intrinsic viscosity, which we show to be highly sensitive to these architectural changes, providing a set of experimental data that both informs and validates the results of molecular simulation. In addition, experimental measurements of hydrodynamic radius from dynamic light scattering are presented as well. These are ultimately compared to Brownian Dynamics simulations that are explicitly parameterized based on known quantities for PNB and PLA (i.e. molecular structure, p ), and exhibit quantitative matching to experimental data that reflects the synthesized molecular architecture. Significantly, we are able to match computer simulations and experimental intrinsic viscosity measurements spanning a broad range of experimentally-relevant bottlebrush architectures, with a simulation model parameterized directly from the bottlebrush chemistry. This contrasts with prior efforts, which have focused on asymptotic limits or scaling laws that provide physical intuition; these are unable to quantitatively predict and visualize the conformations of synthesized bottlebrushes, which are not typically long enough to exhibit universal behavior. We show that a combined experimental/computational approach is able to provide predictions for the molecular structure of bottlebrushes in the synthetically-accessible window of molecular architectures, which can be used to calculate size and shape parameters that are crucial to molecular engineering applications yet difficult to predict from prior theoretical or experimental approaches.