Though our superheated planet and the calendar might not agree, the glorious season of short Friday workdays that we call “summer” kicks off this weekend. For you, that might mean a diminished sense of inhibition about eating with your hands, living with sand, and guzzling cheap sparkling wine. And we’re down with all of that. But for Vanity Fair’s car department, it also means convertibles—and the brasher, flashier, and classier, the better.

Author: Brett Berk | Photography: Ferrari SpA


The 166 was Ferrari’s first grand touring road car. It was built for long-distance luxury cruising, but it had enough power and capability that it could also be raced, should the discerning owner so desire. Curvaceous, dynamic, and quick, it set the template for the future of the brand’s convertibles.

1957-1958 250 Testa Rossa

Only around 34 Testa Rossas were made, intended for racing. Four sensuous fenders, a long hood, and a short deck wrapped around a glorious 12-cylinder engine and track-worthy suspension. (The engine’s top was painted red, hence the name testa rossa, or “redhead.”) Would you like to buy one now? Expect to pay around $39 million, give or take (likely, give).

1960-1962 250 GT SWB California Spyder

Forever immortalized as the Ferris Bueller car, the California Spyder—of which only about 55 were made—was not only gorgeous and fast, it was a celebrity magnet. Alain Delon and James Coburn each had one. So did producer-director Roger Vadim, pictured here, who purchased it for his bombshell wife Brigitte Bardot.

1967-1968 275 GTB/4 N.A.R.T. Spyder

Steve McQueen owned one of these cars. Faye Dunaway drove one in The Thomas Crown Affair. Only 10 were built to commemorate Ferrari’s North American Racing Team (hence the N.A.R.T. acronym). One sold recently for $27.5 million. And, just look at it. Do you need further convincing?

1971-1973 365 GTS/4

Everyone remembers Don Johnson’s outrageous white Testarossa from Miami Vice. But you may not recall that for the show’s first two seasons, Don drove a black 365 GTS/4: an angular-yet-ovoid exemplar of 1970s design.

1977-1989 308/238 GTS

Two words: Magnum, P.I. Ferrari’s most popular car ever, while not a true convertible, owes its commercial success (and placement in this list) in part to Tom Selleck's mustachioed muscularity. If you’re wondering where the engine is, it’s just behind the seats, providing excellent handling capabilities—and close access to the delightful wail of the V8 motor when the Targa top is removed.

1983-1985 Mondial QV Cabriolet

The Mondial’s razor-sharp, high-shouldered design seems inspired by the era’s power suits, lending it a distinct silhouette. It was the world’s only four-passenger, mid-engine convertible, answering unique packaging questions no one ever asked before, or since. We dig it, but current values reflect its under-appreciated stepchild status: ideal examples can still be had for under $30,000.

1995 F50

To celebrate their 50th birthday, Ferrari released this brazen, basket-handled, $500,000 tub, equipped with two seats and the howling V12 engine from their Formula One racecar. The F50 is part of a long line of Ferrari supercars dating back to the 1960s, but is the only one made in a topless variant.

2000 550 Barchetta Pininfarina

After a lapse of nearly 25 years, Ferrari returned to building powerful, luxurious, front-engined, V12-powered, two-seat grand touring cars with the 550. This limited-edition retro-styled roadster version was meant to evoke many of the iconic convertibles featured in this list.

2005 Superamerica

The roof on the Superamerica was made of electrochromic glass, which could adjust its tint from crystal clear to total blackout at the touch of a button. It could also flip back at the touch of another. Ferrari called it “Revocromico.” We call it stunning.

2005 F430 Spider

Peek-a-boo! Ferrari was really into novel uses of transparent materials back in the aughts. Perhaps they were influenced by the concurrent development of molecular gastronomy, in which foamy food is served in a cloche filled with scented steam. Regardless, this engine-under-glass arrangement looks delicious.

2012 458 Spider

The Ferrari 458 is, in our opinion, the greatest road car in the world. When we drove the convertible version a few years back, we found it possessed of all of the closed coupe’s best features, and then some. We have nothing more to add.

2015 California T

The “T” suffix stands for turbocharged, the first Ferrari road car to use this power- and efficiency-boosting technology in nearly 30 years. With a retractable hardtop, four seats, and an ample trunk, the California is built for comfort and speed. We proved this by rushing to a rural viewing of Mad Max: Fury Road, top down, in a light rain. If you don’t slow down, the droplets can’t hit you.