When a man of a certain age buys a fire-engine-red Lamborghini, it brings to mind a particular word (one that begins with douche and ends with bag). But falling for the sexy curves of a 1962 Shelby Cobra—celebrating its 50th anniversary this year—is the act of a sophisticated man of taste. And this vintage ride is obtainable. While a first-edition Cobra can easily cost millions, a faithful re-creation by the original manufacturer is $145,000. It's built from scratch around a tube-frame chassis and can hit 60 mph in 4.5 seconds. But you don't care about all that—you just want to be seen driving it. shelbyautos.com
Top model: 1967 Chevrolet Corvette Sting Ray
What makes it hot: A purist backlash against obsessively restored classics has made "survivors"— either "barn finds" or family heirlooms—suddenly more valuable. This Corvette, with its original Marina Blue paint, drew $227,500 at Mecum Auctions recently, but less precious fifties and early-sixties Vettes can be had for $45,000.
Buying advice: Survivors are often more reliable rides than restorations, because the quality of a makeover can vary wildly. Just don't fixate on whether every last bolt is factory original. To see the best, attend a trade show that specializes in high-end specimens, such as Bloomington Gold.
Top model: 1968 Mercedes SL Pagoda
What makes it hot: If you want to spend more time behind the wheel than under the hood, look to these elegant, pagoda-roof coupes built between '63 and '71. These Benzes are comfortable and indestructible while still sports cars at heart. And at about $50,000 in solid condition, Pagodas cost half the price of brand-new SLs and will turn twice as many heads.
Buying advice: Join an online owners club like the Pagoda SL Group, where Benz lovers use their experiences to guide neophytes through purchase and upkeep. For other low-maintenance gems, look at some vintage American models—especially muscle cars like Mustangs, Chevelles, and Chargers.
RETRO WITH HIGH-TECH GUTS
Top model: 1971 Porsche 911S modified by Singer
What makes it hot: A prime example of the "resto-mod" movement, the 911 by L.A.'s Singer Vehicle Design is a nineties Porsche (the last of the air-cooled models) rebuilt to look like the seminal 1971 edition—but with a carbon-fiber shell, a 360-hp Cosworth racing engine, and an iPod system hidden behind the Blaupunkt radio. The result is a frozen-in-amber sports car with modern drivability, for $255,000.
Buying advice: Tighter budget? Check out Icon's dazzling re-creations of the Toyota FJ40 Land Cruiser or the cosmetically and mechanically tricked-out Camaros by Baldwin-Motion.
A SEXY BARGAIN
Top model: 1967 Austin-Healey 3000 Mark III BJ8
What makes it hot: While museum-quality cars—or "trailer queens"—have held their value, the recession has hammered prices for underdogs, and the low-slung Austin-Healey is considered the poor man's Jaguar. A well-kept, walnut-veneered Mark III BJ8 can be had for $50,000 or less, but experts expect its value to rebound to $75,000 within five years.
Buying advice: Attend auctions—without your checkbook—like the reputable Russo and Steele, Barrett-Jackson, and RM, and look for deals like a 1986 BMW M3, the first generation of BMW's sport sedan, or a 1976 TR6, the last of the Triumph roadsters.