In recent years, classical limits of scattering amplitudes have emerged as a powerful tool for deriving state-of-the-art results for gravitational wave observables from interacting binary compact objects. In this talk, I will explore how gravitational dressing operators within the worldline formalism can be used to derive key radiative observables, including waveforms, emitted momentum, and angular momentum. Specifically, I will show how a gravitational dressing operator, expanded in a multiple soft graviton (low-frequency) limit, can be systematically derived from fluctuations around the asymptotic trajectories of scattered compact objects. This framework enables the extraction of late-time limits of radiative observables. We compute radiative observables to second and higher order in Newton's constant by considering dressing operators up to collinear double soft graviton terms. I will also present results from an ongoing collaboration, where we demonstrate that the graviton dressing exponent, up to double soft graviton terms, recovers the known double soft graviton factor for scattering amplitudes.