We present photometric and spectroscopic observations of the 03fg-like type Ia supernova (SN Ia) ASASSN-15hy from the ultraviolet (UV) to the near-infrared (NIR). ASASSN-15hy shares many of the hallmark characteristics of 03fg-like SNe Ia, previously referred to as "super-Chandrasekhar" SNe Ia. It is bright in the UV and NIR, lacks a clear i-band secondary maximum, shows a strong and persistent C ii feature, and has a low Si ii λ6355 velocity. However, some of its properties are also extreme among the subgroup. ASASSN-15hy is under-luminous (M B,peak =−19.14 +0.11 −0.16 mag), red ((B − V ) Bmax = 0.18 +0.01 −0.03 mag), yet slowly declining (∆m 15 (B)=0.72 ± 0.04 mag). It has the most delayed onset of the i-band maximum of any 03fg-like SN. ASASSN-15hy lacks the prominent H-band break emission feature that is typically present during the first month past maximum in normal SNe Ia. Such events may be a potential problem for high-redshift SN Ia cosmology. ASASSN-15hy may be explained in the context of an explosion of a degenerate core inside a non-degenerate envelope. The explosion impacting the non-degenerate envelope with a large mass provides additional luminosity and low ejecta velocities.