2020 Edition: Drive Like a Boss for Under $20K (Without Faking It)

Factor in depreciation, and you’re losing money to drive a car that is uninspiring on its best day.

This is actually how it should be. The essence of living high for low cost is knowing when you can let the self-indulgent suckers eat the cost of something, and get that same beautiful thing later for a far better price.

And at $20,000, financing for one of these cars is not bad at all:

And if you’re smart now, then someday, you might be able to be as smug about your choice in automobiles as the Chairman:

You buy a Ferrari when you want to be someone. You buy a Lamborghini when you are someone.

Frank Sinatra

For us, a car has to meet a few criteria before it can be considered for selection:

Don’t read this wrong –this is a very good thing. A car that is fully depreciated means that you can get a stellar ride at the lowest price this side of an accident recovery.

Well Optioned
One of the keys here is to get a car that has more than just bare cloth seats and hand crank windows. To be a great value AND have the image we want, some options above base are necessary.

Luxury Spirit
A car doesn’t have to be a German sedan to have luxury, but we’re looking for cars that look the part without going overboard and making you look like a poseur (no 1981 Rolls Royce Silver Spirits with questionable provenance).

Reasonable Repairs and Insurance
Even though you might look like you’re balling, you are still not rich, remember? Can you get an V12 Mercedes for under twenty? Yep. Can you afford it when one of the two turbos blows? Sorry, but that thing is effectively bricked. Don’t be seduced into forgetting to look forward a few months.

Life Affirming
Any car worth buying makes you love driving when you get in it. It makes you steal a glance out the window to the driveway as you head to the kitchen. You find little excuses and errands just for a chance to drive it. Because one of the first rules of notyetjetset is, if you don’t absolutely love it, why buy it?

Good on the ground rules? Here’s one more: DO NOT take our advice. This is our opinion, and shouldn’t be construed as anything else. Buying a car is serious business, and we’re not responsible for your bad decisions.

We good? Alright, here we go:

Compact Sedan: 2017+ Jaguar XE

We’re huge fans of this car. The XE is the baby Jag sedan that inherited the good looks of its big brother, the XF, but with a smaller price tag and size. The XE has been praised as a real handler (especially in S-spec trim), with a dynamic, engaging drive.

“The Jag feels lighter and considerably more nimble than the BMW [3-Series].


Jaguar XE vs. BMW 3-Series

The XE is Jag’s direct stab at the venerable (and gradually less and less exciting) BMW 3-Series. Make no mistake, in terms of build quality, interior materials and finish, and most other objective metrics, the 3-Series is still king. Even so, the Jag has something that you can’t put your finger on, some je ne sais quoi that may just be its kind of waggish, British Jag-iness. You’ll certainly not be lost in the sea of strivers in nearly identical (and kind of boring) BMW 3-Serieses on the road.

The car is also available in rear-wheel and all-wheel drive variants, and in 4 cylinder petrol, diesel, and 6-cylinder petrol engines.

Find used Jaguar XE cars for under $20,000 at


Compact Sedan Honorable Mentions

2015+ Cadillac ATS

Certainly has drawbacks, but the 2.0 turbo engine coupled with an incredibly nimble chassis make for more fun driving than almost any luxury sedan. Interior is… mid-management quality. In-car entertainment and control system (called CUE) is absolutely abysmal.

Find Cadillac ATS for under $20,000 at

2016+ BMW 3-Series

The BMW 3-series will ALWAYS be the king, in a way. It invented this segment, and it’s been at the top forever. The newest 3-series (save the righteous M3) are, to these eyes, a bit boring. Can’t be beaten for build quality and teutonic intelligence.

Find BMW 3-Series for under $20,000 at

Full Size Sedan: 2013-2014 Audi A7

The Audi A7 was released in 2012 as the slightly upmarket, liftback version of the venerable Audi A6. With remarkable styling, excellent performance, and sumptuous interiors, the A7 is an amazing value for money.

After its release, the Audi A7 was named International Car of the Year, and won car of the year awards from the likes of Automobile Magazine, AutoWeek, and Esquire. It shares drivetrain options with the A6, which in the US means a 3.0 TFSI Supercharged 6-cylinder putting out just over 300 horsepower.

For our money, the A7’s interior (and all higher-end Audis) is one of the best of the era, and every inch is leather, wood, and aluminum. The car comes in three trim levels (as do all Audis), starting at Premium, then Premium Plus, and finally Prestige.

Drawbacks of the A7 are less headroom in the back than a comparable Audi A6 due to the sloped (and very lovely) roofline to accommodate the liftback design. Also, because this car is a few years old, most of the affordable examples have a few miles on them. Those in the range of sub-$20,000 are generally somewhere between 60,000 to 100,000 miles. I still recommend it, as it’s a stout, reliable car with an extremely high level of build quality. I have personally had an A6 of the same vintage (meaning same mechanicals) running toward 140,000 miles without issue.


Full-Size Sedan Honorable Mentions

2016+ Audi A6

For a little less money, you can grab an Audi A6, which is still absolutely fabulous for the price. It comes in 3.0L six-cylinder and turbo 4-cylinder trim, so you can jump down an engine size and save even more (in exchange for 100 horsepower).

Find Audi A6 for under $20,000 at

2016+ Mercedes E-Class

A solid, luxurious sedan with a great pedigree. Recent redesign in this model year and above, and available under $20,000 with reasonable mileage. Like all Germans, however, repairs and parts can take a bite out of the wallet.

Find Mercedes E-Class for under $20,000 at

Compact SUV: 2014-2016 Lexus NX200t

Let’s state the obvious: the styling of modern Lexus vehicles is… well, polarizing. They have plenty of detractors (us frequently among them), but we’re going to say that the NX200t is one of the exceptions to that rule. It’s certainly distinctive, and standing out in the crowd is one of the goals here. That particular elephant in the room dealt with, here’s why we think it’s worth a mention here:

Lexus NX200t Reliability

Lexus is made by Toyota, and Toyota is simply one of the most reliable cars on the road, full stop. You will more than likely get off very easy on repairs and maintenance, as Lexus has an “Excellent” reliability rating on RepairPal, with an average yearly cost of $690 to maintain and repair a Lexus NX200t.

Lexus NX200t Value

The other great thing about the Lexus NX200t is that it’s Japanese, and by and large Japanese cars don’t lose their value as rapidly as makes from other countries — especially luxury cars.

The Styling (Again?)

Yeah, yeah. It’s just worth mentioning because like we said — it’s polarizing. The newer generation of Lexuses (Lexii?) are designed to stand out, and the NX200t, while milder than many other vehicles from the make, still manages to stand out in spades.


Sports Car: 2004-2008 Porsche Boxster

Come on, it’s a Porsche — and it’s gorgeous. And it’s a convertible. Plus, because Porsche restyles their cars once every half-century, the second-generation Boxster still looks very current. It would take an enthusiast to point out that this was a decade-old car. That means you don’t look like a poseur.

You could, of course, get the hardtop variant of the Boxster, the Cayman, for roughly the same price but let’s be honest, a convertible is one of life’s great pleasures. You owe it to yourself if you’ve never owned one.

Boxsters are also beautifully balanced (being mid-engined), handle wonderfully, and have powertrains with sufficient go. Engines in this era range from 225 to 304 horsepower, depending on year and trim level. You can also get them with relatively low mileage at this price point. The ones we saw recently were in the 40K to 80K miles range.

Porsche Boxster Drawbacks

The big drawback: Consumables on any German, and especially a Porsche, are stupid expensive, along with most service.

A set of OEM brake pads — you really should use OEM parts — for this lovely slice of automotive excellence? $119 if you have the base model. $348 (!) if you have the S model. (Source: Gaudin Porsche). Compare that with the Cadillac above, whose pads cost half as much at $58.

Moral of the story: Don’t ride the brakes.

Finally, a big caveat emptor: there is a known issue with about 10% of the pre-2006 engines, where the intermediate shaft ball bearings will go out. This is bad. New engine bad. Make sure you take it to the mechanic before you buy.


Sports Car Honorable Mentions

2017+ Fiat 124 Spider

A sister car to the Mazda Miata, but with a healthy dose of Italian style, inside and outside. As any car lover knows, there is NOTHING sweeter than an Italian roadster. A solid example can be had for less the $15k.

Find Fiat 124 Roadster for under $20,000 at

2017+ Nissan 370Z

Big, burly and anachronistic, the last Z car is a blast from the sports car past. Not overloaded with toys and tech, just a fabulous driving experience. Plus, comes in coupe or convertible. Not luxurious by any stretch, but a very fine sports car.

Find Nissan 370Z for under $20,000 at

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