Optical waveguides in the form of glass fibers are the backbone of global telecommunication networks. In such optical fibers, the light is guided over long distances by continuous total internal reflection which occurs at the interface between the fiber core with a higher refractive index and the lower index cladding. Although this mechanism ensures that no light escapes from the waveguide, it gives rise to an evanescent field in the cladding. While this field is protected from interacting with the environment in standard optical fibers, it is routinely employed in air- or vacuum-clad fibers in order to efficiently couple light fields to optical components or emitters using, e.g., tapered optical fiber couplers. Remarkably, the strong confinement imposed by the latter can lead to significant coupling of the lights spin and orbital angular momentum. Taking advantage of this effect, we demonstrate the controlled directional spontaneous emission of light by quantum emitters into a sub-wavelength-diameter waveguide. The effect is investigated in a paradigmatic setting, comprising cesium atoms which are located in the vicinity of a vacuum-clad silica nanofiber. We experimentally observe an asymmetry higher than 10:1 in the emission rates into the counterpropagating fundamental guided modes of the nanofiber. Moreover, we demonstrate that this asymmetry can be tailored by state preparation and suitable excitation of the quantum emitters. We expect our results to have important implications for research in nanophotonics and quantum optics and for implementations of integrated optical signal processing in the classical as well as in the quantum regime.