Convertibles have always sparked strong opinions—but for those who love them, they offer an experience no hardtop can match. Sure, they’ve picked up a few clichés over the years, but as Rob Margeit of Drive Australia rightly pointed out, most of the criticism comes from outdated stereotypes.
“Affordable” is where things get tricky. What feels attainable to one enthusiast might be completely out of reach for another. Instead of pretending there’s one universal price cutoff, we treated affordability as relative. Many of these cars sit below the eye-watering money of modern exotics or brand-new luxury metal, especially on the used market, yet still deliver serious presence and style.
With that in mind, we cross-sampled a mix of 2000s convertibles that turn heads first and worry about lap times second. Some are genuinely budget-friendly, others are more “aspirational but not totally insane,” but all of them offer that special feeling of dropping the top and driving something that looks far more expensive than it is.
We chose these convertibles based on personal opinions about their designs. To make the cut, they had to be available from 2000 to 2009 and offer either a full-folding roof. Whenever we discuss the driving experience, we rely on impressions from respected automotive journalists. With all that out of the way, let’s take a look at some of the best-looking drop-tops to come out of this beloved decade.
Audi TT (Second Generation)
While the first-gen TT receives most of the glory, the second-gen version, launched in 2006, refined everything that made the original great. It kept the curvy, Bauhaus-inspired silhouette but added sharper lines, a bolder grille, and sleeker rear lights.
This was also the first TT available as a hardcore RS variant, which is a major bonus in our books. As Matt Saunders of Autocar noted, it offered a fantastic blend of style and performance, proving Audi knew how to evolve a design without ruining it.
Plymouth Prowler
It may have debuted in the late ’90s, but the Prowler carried into the early 2000s, and it continues to turn heads today. A retro-futuristic hot rod with exposed suspension arms, a V-shaped body, and wild staggered wheels, the Prowler was Mopar’s bold, experimental design statement at a time when nobody else was building anything like it.
Yes, it came only with a V6 and an automatic, as Christian Seabaugh of MotorTrend noted, but that never stopped it from becoming an icon. In colors like its signature purple, the Prowler has a presence that’s impossible to ignore — a reminder that some cars exist simply to stand out and spark conversations every time they roll by.
Mercedes-Benz CLK
The second-generation Mercedes CLK dates back to a time when Mercedes’ two-door cars had completely different naming conventions, and it was also a priority for these models to look gorgeous.
The second-gen CLK blended the elegance of the W211 E-Class with the sleekness of a coupe-convertible, making it one of Merc’s most graceful two-doors. Truthfully, it looks good in any specification, but the various shades of blue and gold gave it an even more classy look. It might not be as fancy as the flagship CL-Class, but the CLK is a pretty good bet, and it’s a stunner.
Ford Mustang GT Convertible (S197-1)
The S197 Mustang nailed the retro revival trend of the 2000s better than nearly any other car. With its throwback grille, fog lights, and tri-bar taillights, it screamed muscle car nostalgia.
While it wasn’t the sharpest handler in the bunch, it still delivered a fun, laid-back driving experience that matched its bold design.
Pontiac Solstice
A Miata fighter from Pontiac? You bet. With a short wheelbase, RWD, and a focus on handling, the Solstice punched above its weight. The GXP version, with turbo power and aggressive bodywork, took it even further.
Dave VanderWerp of Car and Driver praised its responsiveness, but even when parked, the curvy body and wide stance spoke volumes. Proof that GM could make a roadster look seriously good.
Honda S2000
The S2000 didn’t just look good — it sounded incredible. Its high-revving, 240-hp 2.0-liter engine could scream to 9,000 RPM, as shown off by AutoTopNL and confirmed by Larry Webster of Car and Driver. That redline also meant it had one of the highest specific outputs of any production car.
And yet, it was also an aesthetic triumph. Low, sleek, perfectly proportioned, the S2000 is easily one of Honda’s finest-ever designs. No frills. No fluff. Just a pure, beautiful driver’s car.
Mercedes-Benz SL (R230)
If the aforementioned CLK was stylish, the SL was outright glamorous. The R230 SL carried the legacy of the R129 into the 21st century with softer curves and a retractable hardtop. It’s especially desirable with the iconic dialpad wheels.
It had all the right powertrains and presence to match. Whether you went for the V8, the V12, or even the AMG version, this SL looked every bit the executive dream convertible.
Mazda Miata (NB)
Within the world of Miatas, it’s easy to see why the NA Miata, with its pop-up headlights, would get all the attention. We get it; it’s cute, and the pop-ups will steal your heart every time. It’s time for its successor to receive a little more attention.
The NB Miata arrived in the early 2000s, and immediately, it completely eliminated the pop-up headlights. Makes sense, as regulations were getting tighter by this point, but that doesn’t mean we should shun the NB Miata. It’s still tiny, drives exceptionally well, as Patrick Bedard of Car and Driver can confirm, and looks amazing. As good as it is in stock form, the Mazdaspeed version, which Barry Winfield, also of Car and Driver, loved, with its larger wheels and ground effects, is even better.
Aston Martin V8 Vantage Roadster
It’s basically impossible for Aston Martin to mess up styling. The latest models are great, but they’re a bit sharper and more in your face than before. Rewind the clock back to the 2000s, and Aston was all about smoothness and elegance.
This is evident in, among other things, the V8 Vantage. Launched in the mid-2000s as an entry-level Aston Martin model, convertible or hardtop, this is easily one of the best-looking cars of the decade. The 4.3-liter V8 under the hood also produced a rather glorious noise.
Jaguar XK (X150)
The second-gen XK ditched the classic thin body of the X100 for a wider, more athletic design. And it worked really well. With that signature long hood, short rear end, rear-wheel drive, and V8 power, it was a gentleman’s GT car with the heart of a sports car.
A perfect blend of old-world elegance and modern power, the XK was a convertible that looked just as good cruising the Riviera as it did parked at the golf club.
Dodge Viper
How about something a little more extreme? The Dodge Viper was America’s idea of a world-challenging sports car, and what made it stand out was that it was done in the most American way possible. Forced induction? Smaller engine? Fewer cylinders? No, a V10 8.3 liters in capacity and a fascinating story, as told by VisioRacer on YouTube.
The ZB I, or third-generation Viper, doesn’t really get all that much attention, as everyone is too busy extracting a gazillion horsepower from the most recent one or talking about how crazy the first gen is. The third-generation Viper bears a strong resemblance to its predecessors. Still, it has cleaner bodywork, the Dodge crosshair grille works really well, and it has a whole lot of presence, especially with the massive chrome wheels.
Mitsubishi Eclipse Spyder (DK2A)
It wasn’t the fastest, nor the sharpest, but the final-gen Eclipse Spyder sure looked the part. Sleeker and more mature than its predecessor, the DK2A features swooping lines and bold colors, including that unforgettable burnt orange.
Things got even better after the facelift, and with that bright orange paint scheme and the Y-spoke wheels that the facelift cars had, it was definitely a great piece of design. It’s a shame about the underwhelming driving experience, as members of MotorTrend staff confirmed back in the day.
Volvo C70
Volvo and convertibles aren’t two things you normally associate, but the second-gen C70 changed that. With a folding hardtop and timeless Scandinavian design, it was both stylish and practical.
The available 2.5-liter turbocharged five-cylinder also produced a decent sound with the roof down. Safe, smooth, and unexpectedly good-looking, exactly what you’d expect from Volvo’s golden era.
Lamborghini Gallardo Spyder
When most people hear “Lamborghini,” the word affordable isn’t exactly the first thing that comes to mind. These are the cars that lived on posters, not in driveways, especially for those of us who grew up staring at Diablos and Countachs taped to bedroom walls.
But the Gallardo Spyder is the rare exception where depreciation has worked in the buyer’s favor. Thanks to its long production run and its shared architecture with the Audi R8, the Gallardo became one of the most accessible ways to step into Lamborghini ownership. That doesn’t mean it’s cheap to run; it’s still an exotic Italian supercar, not an economy sedan. Still, many owners are surprised to find maintenance costs noticeably lower than the stereotypes suggest.
The design still delivers full Lamborghini drama, and dropping the top only makes it more intoxicating. As Florin Profir and Tudor Serban of Autoevolution report, the Gallardo was engineered during the Audi era, blending daily usability with genuine exotic flair. Add in the even-firing V10’s unforgettable soundtrack, and you get a convertible that looks and feels every bit like the poster car you dreamed of — just without the poster-car price tag.
Cadillac XLR
Built on the C6 Corvette platform but wrapped in sharp Cadillac sheet metal, the XLR was GM’s bold attempt to take on the Mercedes SL. With angular styling, a folding hardtop, and a Northstar V8, it was every bit the showboat it set out to be.
Luxury, performance, and Corvette bones; the XLR is an underrated gem from Cadillac’s design-forward era. The XLR’s downfall was the decision to use Cadillac’s infamous Northstar V8, a bold choice that proved a bit too ambitious under the Cadillac luxury banner.
Mini Convertible
Finally, how about something simple but awesome? After BMW took over the Rover Group to relaunch the Mini, it decided that the Mini lineup needed to expand significantly. This included, among other things, a convertible version of the famous retro hatch.
Boom! The Mini Convertible was born. Every generation of the Mini so far has been (and still is) available as a convertible; however, we’ll focus on the original R52 here. The Mini is already one of the most charismatic small cars, but when you take the roof off, it becomes even more of a joy to look at. Add some extra fog lights and a good set of wheels, and it’s guaranteed to turn heads. It’s also worth mentioning that, yes, you can opt for the Convertible with the lovely supercharged four-cylinder as well.
These Convertibles Are The Fairest Of Them All
While there have been some convertible mishaps, such as the Chrysler PT Cruiser Convertible, it’s generally quite difficult to mess things up when it comes to styling a convertible. For many of them, it feels as though chopping the roof off should have happened immediately.
Of all the convertibles that automakers served us throughout the 2000s, perhaps the last decade when automakers really took this segment seriously, these models are the best-looking of them all.