Some progenitor models of gamma-ray bursts (GRBs; e.g., collapsars) may produce anisotropic jets in which the energy per unit solid angle is a power-law function of the angle (∝θ-k). We calculate light curves and spectra for GRB afterglows when such jets expand either in the interstellar medium or in the wind medium. In particular, we take into account two kinds of wind: one (n ∝ r-3/2) possibly from a typical red supergiant star and another (n ∝ r-2) possibly from a Wolf-Rayet star. We find that in each type of medium, one break appears in the late-time afterglow light curve for small k but becomes weaker and smoother as k increases. When k ≥ 2, the break seems to disappear, but the afterglow decays rapidly. Thus, one expects that the emission from expanding, highly anisotropic jets provides a plausible explanation for some rapidly fading afterglows whose light curves have no break. We also present good fits to the optical afterglow light curve of GRB 991208. Finally, we argue that this burst might arise from a highly anisotropic jet expanding in the wind (n ∝ r-3/2) from a red supergiant to interpret the observed radio to optical band afterglow data (spectrum and light curve).