This chapter focuses on the design of dual band flexible wearable antennas for modern 5G applications to integrate on a smartwatch. The first is a rectangular antenna which the patch and the ground etched on new flexible material is called ULTRALAM® 3850HT. This antenna is designed to operate at 38 GHz and 60 GHz. The second is a planar inverted-2F wearable antenna pasted on a jeans textile material. Two methods for measuring the dielectric properties of the jeans will be presented. This antenna is designed to operate at 28 GHz and 38 GHz. The SAR (specific absorption ratio) is also introduced and SAR results will be shown. Moreover, the proposed smartwatch under the bent condition will be also studied. These antennas are simulated using HFSS and CST 2018.