Present‐day stress directions interpreted from well bore breakouts adjacent to two crastal‐scale, active, strike‐slip faults (the San Andreas fault in California and the Great Sumatran fault in Sumatra) indicate that the maximum horizontal stress direction (SH) is oriented at a high angle (70°–90°) to both faults. The regionally defined stress fields spanning these faults show that adjacent young or actively growing folds have formed orthogonal to SH and are therefore in the thrust‐fault orientation. These observations indicate a decoupling of the strike‐slip and compressional components of the deformation within these broadly transpressive zones. Borehole breakouts in 118 wells in western California indicate a regionally consistent stress pattern with SH generally oriented NE‐SW, nearly perpendicular (80°–90°) to the strike of the San Andreas fault. The orientation of SH nearly perpendicular to the San Andreas fault implies low shear stress on the fault and is consistent with geological interpretations of the Coast and Transverse Ranges indicating active compressional deformation, fault plane solutions for recent dip‐slip‐style earthquakes, principal stress directions determined from inversion of earthquake focal mechanisms, and induced hydraulic fracture orientations. A stress trajectory map for western California is computed using an iterative statistical algorithm in which observed directional data, such as breakout directions, are used to obtain a model regional stress field. Analysis of well bore breakouts in 25 wells within the central and southern oil districts of Sumatra indicates that the regionally defined SH adjacent to the active Great Sumatran strike‐slip fault is oriented at a high angle (70°–80°) to the fault This orientation of SH is consistent regionally with geologic stress indicators and focal mechanisms of dip‐slip earthquakes. Preliminary analysis of the stress field in the vicinity of the Philippine and Alpine faults suggests SH is also oriented at a high angle to these active strike‐slip faults. Similarly, the minimum horizontal stress Sh is oriented at a high angle to the the Kane and Dead Sea transforms. The observation of SH and Sh in the vicinity of active strike‐slip faults being oriented nearly perpendicular and parallel to the faults suggests that large, crustal‐scale strike‐slip faults may, in general, be inherently weak surfaces.