Stunning Driver: 1959 Ford Fairlane 500 Skyliner

This 1958 Ford Fairlane 500 Skyliner offers its new owner the best of both worlds. It will provide a classic wind-in-the-hair motoring experience on sunny days. However, should the weather turn for the worst, pressing a button will raise its steel top, protecting the occupants from the cold and damp. It is a stunning driver with no apparent needs, and is ideal for those who can’t tackle a project build. I must say a big thank you to Barn Finder Pnuts for spotting the Skyliner listed here on Facebook Marketplace in New Salisbury, Indiana. The seller set their price at $35,000, stating that they are fairly firm with that figure.

Ford was only the second marque to produce a model with a retractable Hardtop when it released the Fairlane 500 Skyliner in 1957. Peugeot broke new ground with the concept in the 1930s, and many manufacturers have revisited the concept in recent years. Ford updated the entire Fairlane range in 1958, with the Skyliner retaining its spot as the premium offering. The seller doesn’t provide a history for our featured car, but its immaculate presentation suggests a restoration. The color combination of Gulfstream Blue and Colonial White looks stunning, with the images revealing no cosmetic issues or shortcomings. The fender skirts won’t appeal to everyone, but they certainly enhance the car’s long, low appearance. The same is true of the Continental Kit, although, given the trunk space the top consumes when retracted, it is probably a wise addition. The seller states that the top works as it should, which is great news because the complicated retraction system can be a nightmare to repair or rebuild. The glass is clear, and the trim is in good condition.

This Skyliner’s interior is trimmed in cloth and vinyl, with the colors matching the exterior paint shades. The condition is noteworthy for the lack of wear and cosmetic issues. The painted surfaces look crisp, and the bright trim is excellent. One challenge with older Convertibles is hiding or disguising substandard interiors with the top lowered. The new owner faces no such problems with this Skyliner, and with a pushbutton radio and a clock, it will feel pretty luxurious.

Ford offered 1958 Skyliner buyers a choice of two engines to power their new purchase. This car’s first owner selected the entry-level 332ci V8, teamed with a three-speed Cruise-O-Matic transmission and power steering. The company’s 1958 Fairlane Sales Brochure quotes power and torque figures of 265hp and 360 ft/lbs, blessing the approximately 4,400 lb Ford with pretty respectable performance. The seller confirms that this Fairlane is numbers-matching, which is good news for those considering its long-term investment potential. Although not stated specifically, it appears that this classic is a turnkey proposition.

Ford sold 20,766 examples of the Fairlane 500 Skyliner during its first production year, although that figure fell to 14,713 vehicles in 1958. It persisted into 1959, when only 12,915 cars left the lot. The problem with the Skyliner wasn’t the execution or the effectiveness of its retractable hardtop. The biggest hurdle Ford faced was the sticker price, which many traditional Ford buyers felt was beyond their means. The Skyliner disappeared at the end of 1959, but manufacturers have introduced a range of models since the turn of the New Millennium featuring a similar system. Interestingly, this is not the first time we have seen this Skyliner. It last appeared in April 2025, listed by the same seller with the same asking price. The Skyliner is a rare bird in a big-picture sense, and the seller’s price looks very realistic. Do you think they will taste success this time?