The location of the Subtropical Front (STF), the boundary between Subtropical and Subantarctic Water in the Southern Ocean is proposed to be influenced by the strength and location of the Southern Hemisphere westerly winds. We use a hydrodynamic hindcast model and recent observations to test if changes in the westerly winds can cause meridional shifts in the STF over interannual to decadal timescales by modulating local Ekman transport. We find that increased, or northward, shifted westerly winds lead to an enhanced northward Ekman transport over large parts of the Southern Ocean, resulting in a northward shift in the STF. Conversely for weaker or southward shifted westerly winds where the STF migrates south. However, this relationship breaks down in regions with strong eddy variability and western boundary current systems. In these regions an increase in westerly winds lead to a southward shift in the STF. Observation data from 2004 to 2019 display a southward shift of STF associated with the positive Southern Annular Mode. However, the shift is smaller than the latitudinal shifts in the location of the zero wind stress curl and maximum westerly winds (−0.4° latitude/decade). This discrepancy is due to positive Ekman trends resulting from the intensification of the westerly winds, which oppose the southward migration. Changes in the Ekman transport and the overall southward shift of the STF have also resulted in an observed positive trend in chlorophyll‐a concentrations south of the STF, which could have ramifications for marine ecosystems and the biological pump in the Southern Ocean.