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Smart windows have shown powerful potential in modulating sunlight and energy management. However, there has not been a single system that can simultaneously possess all desired properties, that is, high compliance, wide tunability, and autonomous regulation. Here, a novel system based on polyhedral oligomeric silsesquioxane crosslinked poloxamer is demonstrated. The as‐synthesized material simultaneously possesses a number of the desired properties for smart windows. In addition, with the incorporation of gold nanorods, the as‐fabricated smart window can be operated in an autonomous fashion with its transmission being modulated automatically upon environmental temperature shifts. Finally, the high toughness and high stretchability (10 000% strain) of the material also pave a way for future applications in wearable displays or flexible window screens.