OLED technology continues to make strides, particularly in display technology with costs decreasing and consumer demand growing. Advances are also seen in OLED solid state lighting (SSL), though broad utilization of this technology is lagging. This situation has prompted extensive R&D to achieve high efficiency SSL devices at cost-effective fabrication. Here we review advances and challenges in enhancing forward light outcoupling from OLEDs. Light outcoupling from conventional bottom (through the transparent anode)-emitting OLEDs is typically ~20%, due largely to losses to external, i.e., substrate waveguide modes, internal waveguide modes between the metal cathode and the anode/substrate interface, and surface plasmon-polariton modes at the metal cathode/organic interface. We address these major photon loss paths, presenting various extraction approaches. Some approaches are devoid of light extraction structures; they include replacing the commonly used ITO anode, manipulating the refractive index of the substrate and/or organic layers, and evaluating emitters with preferential horizontal transition dipoles. Other approaches include the use of enhancing structures such as microlens arrays, scattering layers, patterned substrates, as well as substrates with various buried structures that are planarized by high index layers. A maximal external quantum efficiency as high as 78% was reported for white planarized OLEDs with a hemispherical lens to extract the substrate mode. Light outcoupling from OLEDs on flexible substrates is also addressed, as the latter become of increasing interest for foldable displays and decorative lighting, with plastic substrates being evaluated also for biomedical, wearable, and automotive applications.