Future crewed missions to the Moon will face significant environmental and operational challenges, posing risks to the safety and performance of astronauts navigating its inhospitable surface. Whilst head-up displays (HUDs) have proven effective in providing intuitive navigational support on Earth, the design of novel humanspaceflight solutions typically relies on costly and time-consuming analogue deployments, leaving the potential use of lunar HUDs largely under-explored. This paper explores an alternative approach by simulating navigational HUD concepts in a high-fidelity Virtual Reality (VR) representation of the lunar environment. In evaluating these concepts with astronauts and other aerospace experts (n=25), our mixed methods study demonstrates the efficacy of simulated analogues in facilitating rapid design assessments of early-stage HUD solutions. We illustrate this by elaborating key design challenges and guidelines for future lunar HUDs. In reflecting on the limitations of our approach, we propose directions for future design exploration of human-machine interfaces for the Moon.