In the last decade, Smart Glasses (SG) and augmented reality (AR) technology have gained considerable interest in all production sectors. In the agricultural field, an SG can be considered a valuable device to support farmers and agricultural operators. SGs can be distinguished by technical specification, type of display, interaction system, and specific features. These aspects can affect their integration into farms, influencing users’ experience and the consequent level of performance. The aim of the study was to compare four SGs for AR with different technical characteristics to evaluate their potential integration in agricultural systems. This study analyzed the capability of QR code reading in terms of distance and time of visualization, the audio–video quality of image streaming during conference calls and, finally, the battery life. The results showed different levels of performance in QR code reading for the selected devices, while the audio–video quality in conference calls demonstrated similar results for all the devices. Moreover, the battery life of the SGs ranged from 2 to 7 h per charge cycle, and it was influenced by the type of usage. The findings also underlined the potential use and integration of SGs to support operators during farm management. Specifically, SGs might enable farmers to obtain fast and precise augmented information using markers placed at different points on the farm. In conclusion, the study highlights how the different technical characteristics of SG represent an important factor in the selection of the most appropriate device for a farm.