The Fleetwood Sixty Special occupied a still-higher rung on the Cadillac ladder. This one-model series listed at $6233, and for 1959 it rode the standard 3302mm wheelbase, rather than the exclusive 3378mm stretch it had enjoyed in 1958. Although clearly intended as the most prestigious standard sedan, this six-window model wore more makeup than any other '59 Caddy. Starting on the rear door and sweeping almost to the rear bumper was a huge fake air scoop, outlined by chrome strips that shot forward to the front of the car. The taillight pods on the fins were slathered in chrome, and the hubcaps were the sportier version used on the Eldorados. The Fleetwood name stood out in block letters on the lower front fenders; three rows of jewels sparkled in the rear grille.

The 1960 Fleetwood emerged as a cleaned-up version of the '59, or as Walter McCall noted, it "retrieved some of its traditional dignity." Gone were the fake air scoops and the chrome that surrounded them; gone too were the chrome taillight pods. The fins, although only 25mm lower, looked far more elegant without the bullet taillights. A chrome molding now ran quietly along the bottom edge of the car from behind the front wheel to the end of the tail light. Nine small vertical louvers graced the extreme rear fenders and small cloisonne Fleetwood insignia replaced the larger lettering of the '59. The top sported a leather-grained fabric that matched the body color and the interior combined wool broadcloth and leather.

Dave Hols points out that although most people think the 1963 Pontiac Grand Prix was the first GM car to substantially slash the use of chrome trim, this was not the case. The 1960 Fleetwood was really the first "de-chromed" GM car, and particularly significant because of the Fleetwood's high place in the model lineup.

The Sixty Special Fleetwood sedan had the same standard equipment as the 6200 convertible and all 6300 models. This car was outwardly distinguished by a Fleetwood script on the rear deck, nine vertical bright metal louvers on rear fenders, vertical crest medallions on front fenders and wide full-length bright metal sill underscores which extended to the fender skirts and lower rear quarter panels.