Let's be real before we get started. You're not going to spend a couple of grand on a car and then cruise around town looking like you're part of the one percent. However, if you're trying to follow the life advice of faking it until you have a half-decent budget, it's possible to project a bit of wealth without breaking the bank.
We're going to define that here as a range between $10,000 and $30,000, but, most importantly, we're not taking the cost of ownership after the initial purchase into account. We can't stress this enough when we put these lists together: Luxury car prices depreciate as they age, but maintenance and repairs don't get cheaper.
So, when we point out that our first car, an early 2000's BMW Z4, still looks sharp and expensive today, it's still a BMW, and it costs a lot to keep going.
BMW Z4 (2003–2008)
Generally, you can pick up a 2003 BMW Z4 with around 40,000 miles on the clock for about $10,000.
That's one for the cool affordable cars list and the cheap ones that look expensive. The styling still looks contemporary, and that BMW badge carries weight. It doesn't hurt that it's a hoot to drive and has a choice of two fantastic straight-six engines.
Europeans get the added option of a naturally aspirated inline-four. The inline sixes are the same as the power plants in the E46 3 Series, so definitely read up on those pitfalls. If you're careful, it's not just one of those cheap cars that look good; it's also one that tells other enthusiasts you know what's up.
Infiniti QX30 (2017-2019)
We rarely recommend an Infiniti model, but here's one we can.
The interior is nice and built to last, the engine has some poke to it, and it handles well. It's a genuinely fun and well-screwed-together little crossover with a pep in its stride, and it looks good. Unfortunately for Infinity, it didn't sell well and went out of production in 2019.
Fortunately, for anyone looking for cheap cars that look good, the QX30 fits the bill. You can pick up a 2017 Infiniti QX30 Premium or Sport AWD with under 50,000 miles for just under $20,000. Even if you don't care about projecting an image of wealth, the QX30 fits nicely into the bracket of an excellent cheap car.
Genesis G70 (2019)
The Genesis G70 should be cross-shopped by anyone looking at cool affordable cars.
Unfortunately, since its launch a few years ago, the G70 has been massively underrated by the car-buying public. But, when you see one on the road, it turns heads. New, you're going to pay around $40,000 and look like a baller, but go back a few model years, and you can pick up a 2019 model in a choice of trims and with the 2.0-liter turbo engine for under $30,000.
The engine isn't as strong as the six-cylinder, but it's a plucky little unit and a lot of fun to drive. The chassis is superb, the technology is excellent, and the ride is great. Is it better than a BMW 3 Series? There's not enough in it to say no.
Cadillac ATS (2015)
Speaking of BMW 3 Series competitors, you can pick up an older 2015 ATS in Premium trim for around $25,000 or a Luxury trimmed model for about $18,000.
It's not as sharp as the G70 dynamically, but the ATS is no slouch and is distinctively Cadillac in its looks. For the same money as the Luxury trim, you can pick up a higher mileage sporty model with all-wheel-drive and Brembo brakes and plenty of luxury for the same sort of money.
Unless you're willing to spend more, you'll get the 2.5-liter four-cylinder engine making 202 hp. More money will get you the 321 hp six-cylinder engine. Either way, the ATS has been a great used bargain for a while.
Mercedes S-Class (2012)
You can pick up a ten-year-old Mercedes S-550 with around 65,000 miles on the clock for about $24,000.
If you want even more luxury, you can still pick up great examples for under $30,000. While the S-Class is never ostentatious, it oozes style and money no matter what generation you drive. Plus, you don't get rich and stay rich by buying a new S-Class every year.
An older S-Class is a sign of someone that knows how to make and keep the money. No matter the age, it's one of the most expensive-looking cars you can actually buy cheaply.
Maserati Ghibli (2014-2016)
It would be impossible to talk about cars that look expensive but are cheap without at least one Maserati.
The depreciation on Maserati models is legendary, and there's a reason. If you ignore the cost of ownership, you can pick up a Ghibli S for around $25,000 with 60,000 miles on the clock. The 2014-2016 Ghibli models are in the sweet spot of cost and mileage right now, and it's still the current generation, so nobody can tell it's up to eight years old.
Is it better than a 5 Series BMW? No, but 5 Series are ten a penny on the road. The Ghibli might be flawed, but it has a special something, and it's one of our favorite cheap cars that make you look rich - right up until it bankrupts you, anyway.
Porsche Cayman (2011)
Snobby enthusiasts know it as the poor man's 911, most enthusiasts call it a great Porsche sports car, and the normals just know it's a Porsche.
The Cayman launched in 2005 and shared the same platform as the Boxster (also a great deal used) but as a coupe instead of a roadster. A 2011 model is from the tail end of the second generation and powered by a 2.7-liter engine or a 3.4-liter flat-six for the S trim.
You're likely going to end up with the 2.7-liter engine making around 260 hp, which is plenty for a small seater with Porsche levels of grip and handling. On a list of cool affordable cars, 2011 Caymans land in the sweet spot of somewhere between $25,000 and $30,000.