A method is proposed for distinguishing highly boosted hadronically decaying Ws (W-jets) from QCD-jets using jet substructure. Previous methods, such as the filtering/mass-drop method, can give a factor of ~2 improvement in S/sqrt(B) for jet pT > 200 GeV. In contrast, a multivariate approach including new discriminants such as R-cores, which characterize the shape of the W-jet, subjet planar flow, and grooming-sensitivities is shown to provide a much larger factor of ~5 improvement in S/sqrt(B). For longitudinally polarized Ws, such as those coming from many new physics models, the discrimination is even better. Comparing different Monte Carlo simulations, we observe a sensitivity of some variables to the underlying event; however, even with a conservative estimates, the multivariate approach is very powerful. Applications to semileptonic WW resonance searches and all-hadronic W+jet searches at the LHC are also discussed. Code implementing our W-jet tagging algorithm is publicly available at http://jets.physics.harvard.edu/wtag
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