Maxwellian‐view structure exhibits several advantages in augmented reality (AR) displays, such as high efficiency, always‐in‐focus (no vergence‐accommodation conflict (VAC)), and simple optical structure. However, the bottleneck of Maxwellian‐view is its tiny eyebox. Extensive efforts have been devoted to enlarge the eyebox of the Maxwellian‐view system based on pupil duplication or pupil steering by creating multiple viewing points, however, the important gaze matching is neglected. Once the virtual image center deviates from the user's eye gaze, it will bring an unnatural viewing experience. Herein, a gaze‐matching Maxwellian‐view AR system with an enlarged eyebox is demonstrated. In the meantime, this AR system also maintains the properties of aberration‐free, high efficiency, highly transparent for ambient light, and relatively large field of view. Moreover, two layers of off‐axis cholesteric liquid crystal (CLC) lenses are applied as the optical combiner in the system, which is lightweight and compact. The off‐axis angle of such a CLC lens is as large as 60 degrees, which plays a vital role in future Maxwellian‐view AR headsets.