Allen is older, wiser, and wants to get a classic car. He wants something reliable, but with timeless character, and even though he might not be driving too fast, he wants to look cool. What car should he buy?

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Allen seems to be just fine with the cruise control set at the speed limit, as long has he has a stylish car that makes him feel young. Here is the scenario:

I’m older now and don’t compete on the freeway of life like I used to. I want a classic but functional, vehicle that sends the message “Old Guy driving Cool Car. Please don’t honk at me just because I drive slowly (legally) in the slow lane.”

I live in California so I would like something unique that has some character. I love older Jaguars, but know better about their reliability, and I dearly miss my ‘66 V8 Mustang. I also dig lowriders because they can be a great artistic expression of their owners.

This will be a daily driver so it can’t be too exotic or require a lot of maintenance. It will also need to be big enough to carry kids and some gear. Lastly, I don’t have a garage so this car will be street parked, so nothing too fancy that I have to worry about getting stolen.

Quick Facts:

Budget: $25,000 - $30,000

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Daily Driver: Yes

Expected ownership time: 7 years or more

Wants: Classic, cool, reliable, and functional

Doesn’t want: Something too flashy or expensive to maintain

Expert #1: Tom McParland - Loves The Longroofs Even Old Ones

You want something robust, cool, classic and practical. This problem calls for a wagon. Specifically, a 1966 Chevrolet Bel Air wagon. Similar to your old Mustang, the Chevrolet Bel Air is one of the quintessential classic American cars.

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Space for the kids? Look at those bench seats, you could but a whole damn soccer team in this thing. Remember, before the minivan families toured the country in giant wagons. And with a massive trunk like that you ‘ll never have to worry about cargo area.

Is it cool? Well, to me it looks pretty damn cool as it sits, but with a buy-it-now price of under $21,000 that gives you plenty of buffer, to make for an excellent lowrider platform with a full set of airbags on the corners. Heck, it already has a great custom paint job.

Now even with a 350 cubic-inch V8 this thing isn’t going to be a rocket ship, but man is it going to sound good and look sharp cruising. As far as reliability goes, you know the old saying, “They don’t build ‘em like they used to…” Well, this is how they used to build them. Parts are robust and easily sourced, and it should be a problem finding a mechanic in SoCal that knows his or her way around an old Chevy.

Expert #2: David Tracy - Loves This Jalopmobile

Photo: Craigslist

With your budget, the possibilities are endless. But you came to Jalopnik for answers, so you’re getting a Jalop recommendation. And few cars are more Jalop than the Volkswagen Type 3 Squareback.

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It’s got an air-cooled engine in the back under the floor, it’s rear-wheel drive, manual and it’s a wagon! It’s the ultimate combination of quirky goodness, and you can find examples like this one in good condition for well under 10 grand!

It’s not too fancy, it will fit plenty of kids and gear in the back, and because it’s basically a Beetle underneath, parts should be easy to come by. Plus, it just looks freaking cool.

Expert #3: Patrick George - Knows A Thing Or Two About How To Be ‘Cool’

Allen, I wish I knew a little more about your personal tastes. American? German? Imported butterfly-doored compact cars? You mention the ‘66 Mustang and a Jaguar, so I’m going to guess your tastes run classic and, as you say in your request, not too too exotic.

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Let me say that few cars are as classy as an old Mercedes-Benz. Might I suggest the C123? It is the coupe version of the W123, one of the most successful and ubiquitous Benzes of all time. Most of them weren’t fast—especially the diesels—but they look fantastic and can cruise all day long. Plus, they come from the era of totally overbuilt German cars. Parts are not cheap and these cars are complex, but take care of them and they can run forever. You even get a good back seat and a trunk for gear- and kid-hauling.

That Jaguar you suggested? I think this is a similar option, but a better one. And you can find a great one for well under $30,000. It won’t be hard. This one is perfect for just $14,900. Go live the classic Benz life.