Vintage trucks: Because you don't need to go fast to have fun.
There's a lot to be said for vintage trucks, and the first is that they tend to be cheaper to get into and easier to work on than cars. Older trucks were built to last, and even if they had a rough life they tend to be mechanically simple and easy to rebuild and maintain. Big engines in big engine bays are a playground for the weekend mechanic and, for everyday driving, they're incredibly useful. The only real problem is the number of friends and relatives that remember you have a truck when they need to move something big.
Then there's the style. The big bro-dozers of today are a gross overstatement. They tend to smack of someone trying too hard or making up for something they don't actually have. See someone in a vintage truck though, that's just someone that loves a truck and likes doing practical stuff. The real issue when it comes to shopping for a vintage truck is rust, and how hard a life they've had.
The main tricks to shopping for an older truck is to not go for something obscure unless you already know where to find the parts you'll need, and to be open to alternatives. A good example is looking at GMC trucks as they often shared platforms with Chevy trucks, but truck people tend to want that Chevy badge.
We'll start with the C10 as it's one of the more sought after trucks out there. That's mainly due to its simple but strong mechanics and straight-edge styling that makes for a great canvas to customize on. Unfortunately, early generation prices are on the rise as they appeal to people who can't quite afford to get into muscle cars. However, older 6-cylinder and smaller V8 engined examples can be found in varying states of repair at decent prices. For now, anyway. The later 1973-1987 generation is better priced and what we would be looking for as a project.
The Hilux went by a few names in the United States, including Toyota Pickup and SR5, but it's the same truck that built a global reputation for being incredibly hard to kill. A lot of that is down to the Toyota R line of engines, which have a punch to them as well as the hardiness of a cockroach. The downside is that they are getting harder to find in their factory state. However, if you're willing to undo someone else's work they can be picked up amazingly cheap.
The Dakota was meant to be a shared project with Mitsubishi, but it never made it to Japan in the 80s. We're placing this small-to-mid-size truck over the Chevy S10 and Ford Ranger for only one reason - they tend to be a little cheaper to buy. On top of that, and unlike the S10 and Ranger, in 1991 Dodge offered a big V8 as a factory option. If you really want to stand out, and can find one, there was even a factory convertible option.
Before the Dodge Ram was the third generation of the D-Series truck. We picked out this generation as the cheapest we could find as decent drivers, but if you have the money going earlier brings a little more Americana style. The D-Series was an excellent example of just how robust and well-proportioned vintage trucks can be. If you want a little more cab space, hunt out a Club Cab model.
Unfortunately, the El Camino is becoming an expensive vehicle. If you're not bothered about having the right badge and year to impress the retirement generation though, GMCs version and later G-Body El Caminos are still out there and not so sought after. You won't find an SS El Camino for minimum dollars, but just about every GM V8 swap has been done and well documented if you have a decent garage.
We only chose to highlight the eighth generation because it's the last one that looks truly vintage and amongst the more inexpensive models you'll find. Price aside, the same applies through the range as F-Series trucks and parts are ubiquitous. If you want to go older, 1967-1972 models are still out there and not crazy money. They were also built while Ford was wholly focused on commercial users and the drivetrains are as close to bulletproof as you'll find. If you want as big of a bang for your buck as possible, eighth and ninth generation F-Series are ridiculously plentiful and cheap.
Toyota Hilux isn't the only hard to kill trucks around. The automotive hipster would, rightly, go for the earlier Datsun 620, but there are more 720 models around and we love how they stand out now, but without looking pretentious.
We debated putting this one on the list because interest in these has been steadily growing and spiked recently with Jeep bringing the name back. However, if you do your due diligence, they can still be affordable to buy as a project. The big deal is that they are unique and attention grabbers as well as being rugged and capable through both earlier generations.
Ford rebadged and sold the Mazda B-Series truck as it discovered an unexpected demand for small trucks. The biggest market was California and it sold well, so there are examples out there with very little rust to be had.
Despite the automotive hipsters and the rise of Radwood nostalgia, you can still get a Subaru Bi-drive Recreational All-terrain Transporter for a decent price. All Brats have 4-wheel drive and later models went from a 1.6-liter to a 1.8-liter engine and manual transmissions were standard. That keeps choices and shopping for one simple unless you want a 1983 and 1984 turbocharged model, which could be optioned with an automatic transmission.