Winglets have been used to augment the power extraction of Horizontal Axis Wind Turbines (HAWT). However, despite some understanding on the way they affect the aerodynamics of wind turbines, the influence of specific geometric parameters still requires investigations. To assist with the resolution of this problem, this paper describes the influence of taper ratio and root chord ratio of a winglet on power and thrust coefficients and annual energy output (AEO) of a HAWT. Computational Fluid Dynamics (CFD) simulations obtained the effects by numerically solving the Reynolds-Averaged Navier–Stokes (RANS) equations in steady state using the κ-ω SST turbulence model and a moving reference frame methodology. New Mexico wind turbine experimental data validated the computational results, and computational analyses of the winglets were compared with the validated simulations. The set of winglets is composed by twelve configurations, and the results reveal a higher aerodynamic efficiency with a lower taper ratio and a lower root chord ratio, suggesting winglets can be optimized for enhancing the performance of the horizontal axis wind turbines. Besides that, the AEO is sensitive to the local wind regime and the utilization of winglets is recommended for sites with a medium to high mean wind speed.