In this study, the aim was to synthesize N-glycosidic halochalcone derivatives and to examine their lipase inhibitory activity. The synthesized chalcones (1–3) were well known and the data were compatible with previous findings. However, compounds 4a/b, 5a/b, 6a/b, and 7–9 were synthesized for the first time in the current study. Remarkable lipase inhibitory potentials of the synthesized compounds were further confirmed through molecular docking studies. The highest lipase inhibition activity was experimentally identified for compounds 2 and 5a with IC50 17.7133 ± 0.9648 μg/mL and IC50 22.6521 ± 1.2146 μg/mL, respectively.