A non-attached monitoring device includes monitoring assembly and an antenna configured to radiate signals from the monitoring assembly. The antenna is configured to radiate through the oriented attenuating body of the tire sidewall regardless of the position of the monitoring device with respect to the tire sidewall. In one embodiment, the antenna has a body that is looped back on itself. The body may be parallel to or perpendicular to the antenna ground plane. In another embodiment, a radiating slot antenna is configured to provide transmissions through the tire sidewall regardless of the position of the monitoring device.