The surface wind and stress responses to sea surface temperature (SST) are examined using collocated moored buoy and satellite observations in the Gulf Stream and the eastern equatorial Pacific. Using 17 buoy pairs, differences in the wind speed, 10-m equivalent neutral wind speed (ENW), and surface wind stress magnitude between two buoys separated by between 150 and 350 km were all found to be highly correlated to, and satisfy linear relations with, the SST difference on time scales longer than 10 days. This wind–SST coupling is consistent with previous analyses of spatially high-pass-filtered satellite ENW and SST fields. For all buoy pairs, the ENW and wind speed responses to SST differ by only 10%–30%, indicating that the ENW and stress responses to SST are attributable primarily to the response of the actual surface wind speed to SST rather than to stability. This result clarifies the dynamical pathway of the wind–SST coupling on the oceanic mesoscale. This buoy-pair methodology is used further to evaluate the ENW–SST coupling derived from collocated satellite observations of ENW by the Quick Scatterometer (QuikSCAT) and SST by the Advanced Microwave Scanning Radiometer for Earth Observing System (AMSR-E) on board the Aqua satellite. Overall, the satellite and buoy ENW responses to SST compare well, with normalized mean differences (satellite minus buoy) of 17% over the Gulf Stream and −31% and 2% over the southern and northern sides of the equatorial Pacific, respectively. Finally, seasonal variability of the large-scale ENW is shown to modulate the wind stress response to SST, whereby stronger winter wind enhances the stress response by a factor of ~2 relative to the ENW response.