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Wearable sensors are a topic of interest in medical healthcare monitoring due to their compact size and portability. However, providing power to the wearable sensors for continuous health monitoring applications is a great challenge. As the batteries are bulky and require frequent charging, the integration of the wireless power transfer (WPT) module into wearable and implantable sensors is a popular alternative. The flexible sensors benefit by being wirelessly powered, as it not only expands an individual’s range of motion, but also reduces the overall size and the energy needs. This paper presents the design, modeling, and experimental characterization of flexible square-shaped spiral coils with different scaling factors for WPT systems. The effects of coil scaling factor on inductance, capacitance, resistance, and the quality factor (Q-factor) are modeled, simulated, and experimentally validated for the case of flexible planar coils. The proposed analytical modeling is helpful to estimate the coil parameters without using the time-consuming Finite Element Method (FEM) simulation. The analytical modeling is presented in terms of the scaling factor to find the best-optimized coil dimensions with the maximum Q-factor. This paper also presents the effect of skin contact with the flexible coil in terms of the power transfer efficiency (PTE) to validate the suitability as a wearable sensor. The measurement results at 405 MHz show that when in contact with the skin, the 20 mm× 20 mm receiver (RX) coil achieves a 42% efficiency through the air media for a 10 mm distance between the transmitter (TX) and RX coils.