Changes in style for 1958 model year were limited to the front grille and bumper. Quad headlights were standard. The model year got credit for introducing Cruise Control, called Auto-Pilot and was present on the Imperial, and on Chrysler New Yorker and Windsor models. Another option was the Power door locks. Sales dropped to 16,133 and dealers got frustrated with buyers who referred to Imperials as Chrysler Imperials which inhibited sales. This was because Imperials continued to be sold at Chrysler dealership instead of a standalone dealer despite having a separate “Imperial” dealership sign.

Production was moved from Jefferson Avenue Assembly plant in Detroit to a facility in Warren Avenue, North of the Jefferson Avenue factory in 1959. For this model year, a toothy new grill was introduced and renovations made to the side trim in term of exterior styling. The “Silver crest” roof was the new option featuring a stainless steel front and a rear canopy which could be ordered in any basic car colors or in the “Landau” version that had a black canopy and a leather appearance.

The swivel out front seats were the new option and were a part of the six-way electric front bench seat. This year the seats were manually activated by a handle, and in 1960 they would automatically swivel when front door opened or closed operated by a cable and springs. The Hemi V8 was replaced with a cheaper 413 cu inches “Wedge” head V8 engine with more horsepower and weight of 101 lbs lesser, improving the power-weight ratio.