Supernovae (SNe) are the giant stellar explosions that radiates a huge amountof energy 1051−52erg outshining the entire galaxy endorsing chemical enrichment.Observational classification diversifies SNe into Hydrogen rich and Hydrogen poorsub-class. However, peculiarities exist for which some SNe may gain outer en-velopes due to interaction with circumstellar medium (CSM) while some mayshred outer envelopes due to high stellar winds/accretion. The thesis highlightsthe photometric and spectroscopic studies of SNe with diminishing Hydrogenenvelopes. In our observing campaigns from 2015 to 2019, we selected five ob-jects as representative members of the five subclasses - SNe 2012ab (IIn), 2015as(IIb), 2019uo (Ibn), 2015ap (Ib) and 2016P (Ic). Probing the explosion scenarioand progenitors, estimating physical parameters, host galaxy metallicities, ejectaCSM interaction, mass-loss rates and associated asymmetries are the highlightsof this thesis. Photometric studies of the stripped envelope group (SNe 2015as,2015ap and 2016P) revealed a great diversity in luminosites (Mv=−16.82 mag -−18.15 mag), decay rates (1.1 - 4.5 mag (100 d)−1) and energies (1.1 - 8.6×1051erg). Late time spectroscopic studies of both SNe 2015ap and 2015as indicates ahighly asymmetric ejecta configuration and favour a binary progenitor scenariowith mass between 13 - 20 M. Spectroscopic studies of both the interactingSNe 2012ab and AT2019uo showed an initial P-cygni profile which later becomesdominated by narrow-intermediate emission lines of Hydrogen and Helium, thusindicating onset of ejecta CSM interaction. We detect flash ionisation spectro-scopic signatures for AT2019uo which is the second Type Ibn SN to show suchfeatures after SN 2010al. Light curves of SN 2012ab and AT2019uo points tothe heterogeneity and homogeneity existing among the Type IIn and Type IbnSN subclass respectively. This in turn hints towards a LBV progenitor for SN2012ab and a Hydrogen free WR progenitor for AT2019uo.1