According to the forecast of Allied Market Research, the flexible electronics market is projected to reach $42.48 billion by 2027. It is estimated to revolutionize the lighting technology, power integration displays, and health monitoring systems. The popularity of flexible electronics is mainly due to the unique benefits of organic materials and devices that offer cost-effectiveness, low-temperature processability, mechanical softness, and shape adaptability, [5][6][7] which are difficult to obtain with traditional, complementary-metal-oxide-semiconductor (CMOS)-based rigid systems. [8] Over the past two decades, research interest in flexible electronic systems has grown exponentially, driven by the requirements of interface softness and shape adaptability for electronics used in Internet-of-Things (IoT), [9] human-machine interfaces, [10] and advanced healthcare. [11] Although significant progress has been made in academia, the practical application of flexible electronics in the industry is limited. Presently, thin-film photovoltaics and flexible displays mainly contribute to the flexible electronics market, with a noticeable presence held by radio frequency identification (RFID) tags and medical X-ray imagers. [12] Indeed, much of the success of present flexible electronic systems rely on the performance and reliability of thin-film The development of flexible and conformable devices, whose performance can be maintained while being continuously deformed, provides a significant step toward the realization of next-generation wearable and e-textile applications. Organic field-effect transistors (OFETs) are particularly interesting for flexible and lightweight products, because of their low-temperature solution processability, and the mechanical flexibility of organic materials that endows OFETs the natural compatibility with plastic and biodegradable substrates. Here, an in-depth review of two competing flexible OFET technologies, planar and vertical OFETs (POFETs and VOFETs, respectively) is provided. The electrical, mechanical, and physical properties of POFETs and VOFETs are critically discussed, with a focus on four pivotal applications (integrated logic circuits, light-emitting devices, memories, and sensors). It is pointed out that the flexible function of the relatively newer VOFET technology, along with its perspective on advancing the applicability of flexible POFETs, has not been reviewed so far, and the direct comparison regarding the performance of POFET-and VOFET-based flexible applications is most likely absent. With discussions spanning printed and wearable electronics, materials science, biotechnology, and environmental monitoring, this contribution is a clear stimulus to researchers working in these fields to engage toward the plentiful possibilities that POFETs and VOFETs offer to flexible electronics.