High aspect-ratio micropillars are in strong demand for microtechnology, but their realization remains a difficult challenge, especially when attempted with soft materials. Here we present a direct drawing-based technique for fabricating micropillars with poly(dimethylsiloxane). Despite the material's extreme softness, our technique enables routine realization of micropillars exceeding 2,000 mm in height and 100 in aspect-ratio. It also supports in situ integration of microspheres at the tips of the micropillars. As a validation of the new structure's utility, we configure it into airflow sensors, in which the micropillars and microspheres function as flexible upright waveguides and self-aligned reflectors, respectively. Highlevel bending of the micropillar under an airflow and its optical read-out enables mm s À 1 scale-sensing resolution. This new scheme, which uniquely integrates high aspect-ratio elastomeric micropillars and microspheres self-aligned to them, could widen the scope of soft material-based microdevice technology.