The detonation of a thin (less than or similar to 0.03 M (circle dot)) helium shell (He-shell) atop a similar to 1 M (circle dot) white dwarf (WD) is a promising mechanism to explain normal Type Ia supernovae (SNe Ia), while thicker He-shells and less massive WDs may explain some recently observed peculiar SNe Ia. We present observations of SN 2020jgb, a peculiar SN Ia discovered by the Zwicky Transient Facility (ZTF). Near maximum brightness, SN 2020jgb is slightly subluminous (ZTF g-band absolute magnitude -18.7 mag less than or similar to M ( g ) less than or similar to -18.2 mag depending on the amount of host-galaxy extinction) and shows an unusually red color (0.2 mag less than or similar to g (ZTF) - r (ZTF) less than or similar to 0.4 mag) due to strong line-blanketing blueward of similar to 5000 angstrom. These properties resemble those of SN 2018byg, a peculiar SN Ia consistent with an He-shell double detonation (DDet) SN. Using detailed radiative transfer models, we show that the optical spectroscopic and photometric evolution of SN 2020jgb is broadly consistent with a similar to 0.95-1.00 M (circle dot) (C/O core + He-shell) progenitor ignited by a greater than or similar to 0.1 M (circle dot) He-shell. However, one-dimensional radiative transfer models without non-local-thermodynamic-equilibrium treatment cannot accurately characterize the line-blanketing features, making the actual shell mass uncertain. We detect a prominent absorption feature at similar to 1 mu m in the near-infrared (NIR) spectrum of SN 2020jgb, which might originate from unburnt helium in the outermost ejecta. While the sample size is limited, we find similar 1 mu m features in all the peculiar He-shell DDet candidates with NIR spectra obtained to date. SN 2020jgb is also the first peculiar He-shell DDet SN discovered in a star-forming dwarf galaxy, indisputably showing that He-shell DDet SNe occur in both star-forming and passive galaxies, consistent with the normal SN Ia population.