Increasing levels of nature-oriented sustainability strategies (NOSSs) are being recognized as offering solutions to combat climate change at scale, both through transformative infrastructure and autonomous technology innovations. This paper presents a synopsis of the mainstream literature covering the emerging trends from the last two decades across two broad trajectories of NOSS initiatives—“nature-inspired” (NI)- and “nature-based solution” (NBS)-oriented approaches. The specific scopes of these two approaches have been categorized into disciplinary fields, highlighting their peculiarities and commonalities, followed by an appreciation of their evolutionary trends based on the literature abundance over three distinct time-horizons—pre 2000, 2000–10, and 2011–2021. We find ambitious levels of sustainability-led developments are driving NOSS initiatives beyond 2010; in particular, the increased level of NI approaches in the field of chemical processing, material structure, and renewable energy. Likewise, there has been rapid growth in NBS approaches in the last decade from a systems perspective, reducing the level of grey infrastructure by offering sustainable alternatives to the ecologically destructive technologies. However, we identify some crucial red herrings to the main-streaming of NOSSs as a ‘true sustainability solution’, such as the inherent challenges in their scaling-up, operation and management, and in ensuring ecologically and culturally adaptive interventions across different global contexts.