The Joint Urban 2003 (JUT) project, a cooperative undertaking to study turbulent transport and dispersion in the atmospheric boundary layer conducted in Oklahoma City in the summer of 2003, afforded the U.S. Army Research Laboratory (ARL) the opportunity to leverage our measurement capabilities to increase our understanding of the urban environment and its effects on soldiers and military systems. Our measurement campaign is outlined in a companion presentation; in this paper we concentrate on the boundary layer winds measured in this environment and compare these observations with wind fields produced by a three-dimensional boundary layer wind model developed at ARL. The model was used to simulate the effects of the complex urban canopy on the wind fields in and above the central business district and surrounding areas. The model uses the profiles of wind and temperature from measurements or a larger scale model together with urban structure data including building locations, shapes, sizes, and heights to produce a high-resolution diagnostic wind field in the domain of interest. Terrain elevation and vegetative cover can also be used as inputs. Comparisons between the model results and a number of the measurements obtained during the field campaign are described. Further comparisons with other models and the large set of meteorological and diffusion measurements obtained by other agencies and investigators in Oklahoma City should greatly increase our understanding of the urban boundary layer environment and our ability to predict effects within it.