Old School Cool: 4 Stylish 2 Decade-Old Cars We Can Buy Right Now

Does desirability have any correlation to time? When cars are the subject of discussion, it can be argued in two ways. Sure, new cars nowadays are mostly laden with the fanciest tech and electric motors with neck-strapping performance, satisfying an early adopter’s craving for the latest and greatest. Time in this respect is valued by which manufacturer can churn out the best in the shortest amount of time. Before we know it a facelifted model appears with even faster tech, leading to a vicious circle.

But if we rewind the clock and engage with another variety of car owners, there will be some who appreciate relatively old school metal. It might be due to the effect of nostalgia where a particular model belonged to the family fleet, or simply due to the fact that older cars evoke memories of simpler pre-social media days where information overload was few and far between. The value of time when placed in this context appreciates like fine wine, which in our opinion makes these cars more desirable as years progress.

We’ve prepared a shortlist of two decade-old cars that might have been overlooked a decade ago, but gained traction in recent times perhaps due to their relative rarity and sleek aesthetics (and one with blistering soundtrack to match). They might not be the exact cars featured on our listings - we are certain more will be available but you’d have to be quick!

Based on the Mk4 Volkswagen Golf, the Mk1 Audi TT was lauded more for its looks, rather than dynamic ability. For the latter that unfortunately led to several high profile fatalities on the autobahn during high speed lane changes. It did not get off to a particularly good start, but its launch timing and boutique car looks made it somewhat like a 50s / 60s inspired retro steampunk-like charm back in the day, and a modern classic today. Two engine options were offered - a 1.8-litre turbocharged unit found in this stick shift example, and a 3.2-litre NA VR6 (shared with the Mk4 Golf R32).

Eight model years later with the final batch produced in 2003, the E39 BMW 5 Series barely made it ahead of its E60 successor for the two decade-old timeline. A highlight for the E39 was the dual headlights surrounded by light rings, more commonly known as “angel eyes”. It was a trailblazer from an engineering standpoint too - the E39 was the first mass-produced car made almost entirely out of light alloy. This 3-owner 520i example comes with comfort features such as dual zone climate control and front electric seats. Yes, this was the era where numbers on the boot matched the engine spec - an inline-6, 2.0-litre naturally aspirated engine sits under the bonnet, paired with a 5-speed automatic with manual override.

The 986 Boxster might have a near-identical production timeline to the E39 5 Series, but its existence could not be more different. Born out of “dire straits” in the early 90s as sales of its predecessors (928, 968 and 944) were not up to par, Porsche pushed ahead with its mid-engined Boxster Concept, released it earlier than its 911 sibling (996-gen) and priced the base-spec Boxster slightly lower than entry-level Germans luxury sports sedans. It sounded like an exercise clearly aimed to align balance sheets rather than a project born out of passion. Ironically the 986 had the same bonnet, front wings, headlights, interior and engine components as the 996, so could the 986 be an unintentionally desirable parts bin exercise? We’ll let you decide.

8,800 Ferrari 360 Modenas were built from 1999 to 2004, around 2,000 less than its 355 predecessor. Its rarer status formed only a portion of its appeal though - in another massive feat of engineering to shave weight, the all-aluminium space frame chassis was 40% stiffer, allowing the car to be a significant 28% lighter than the 355. Sharp lines were replaced by masterful visualisations of Pininfarina, the only man capable of making us momentarily neglect the predecessor's epic pop up headlights. This example comes with a bag of goodies, including Novitec springs, carbonfibre interior panel bits and an ECU tune that should make the highly strung 3.6-litre V8 sing like no other on local tarmac.

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