We explore the challenging but phenomenologically interesting hierarchical mass spectrum of the inert doublet model where relatively light dark matter along with much heavier scalar states can fully satisfy the constraints on the relic abundance and also fulfill other theoretical as well as collider and astrophysical bounds. To probe this region of parameter space at the LHC, we propose a signal process that combines up to two large radius boosted jets along with substantial missing transverse momentum. Aided by our intuitive signal selection, we capture a hybrid process where the di-fatjet signal is significantly enhanced by the mono-fatjet contribution with minimal effects on the SM di-fatjet background. Substantiated by the sizable mass difference between the scalars, these boosted jets, originally produced from the hadronic decay of massive vector bosons, still carry the inherent footprint of their root. These features implanted inside the jet substructure can provide additional handles to deal with a large background involving QCD jets. We adopt a multivariate analysis using a boosted decision tree to provide a robust mechanism to explore the hierarchical scenario, which would bring almost the entire available parameter space well within reach of the 14 TeV LHC runs with high luminosity.