A lot of us have differing opinions on Ralph Lauren's iconic polo shirt. Some people think it’s a necessary addition to any man’s wardrobe; some will argue that it’s the emblem of everything wrong and douchey in the Western world. That aside, nobody on the planet has the gall to say a cross word about his ridiculously cool classic car collection.
But from his 1955 Porsche 550 Spiders, for which he shucked out a cool $3,500,000, to his 1938 Bugatti Type 57SC that’s reportedly worth nearly $40,000,000 (nope, not a typo), very few of us can hope to compete with that level of awesomeness. That is, unless we re-think the game.
By dropping two wheels, you can also drop a few decimal points from your bottom line. Of course, it’s still possible to spend an astonishing amount on a motorcycle (anyone remember the 1907 Harley-Davidson Single sold at auction in 2015 for $715,000?), but the savvy shopper can throw some serious flare into his garage without having to sell his wife into slavery.
The deals won’t last, though. With every Brooklyn hipster that buys a vintage Honda, scratches up the paint, slaps a low-profile seat on it, and calls it a “cafe racer,” fewer of these fantastic machines are available each year. And while by no means are any of these bikes listed here considered especially scarce, the day is fast approaching when these babies will ditch their “vintage” labels for the more stately (and costly) “historic.”
Although prices of vintage motorcycles vary widely depending on condition, these numbers are what you should figure to pay for a solid machine you can hop on and ride.
19 1970 Bridgestone 350 GTR- $3,000
Most people associate the name "Bridgestone" with tires–and for good reason. They’ve been deep in the rubber game for nearly 90 years.
But in 1963, Bridgestone founder Shojiro Ishibashi (whose last name means “stone bridge” in Japanese, by the way) became tired of watching Honda make serious bucks off selling their motorcycles donning his tires. The logical next step? Build his own motorcycle around the tires he was already producing.
The company only manufactured them for a limited time (1963-1973) and priced them comparably to the much bigger, more powerful and better reputed Triumph Bonneville, so sales didn’t exactly skyrocket.
But those acquainted with Bridgestone motorcycles tout their reliability, excellent machining quality, and advanced engine, brake, and transmission features as a credit to moto-history. And if you can get your hands on one of these things, you’ll have a great bike with huge upward financial potential.
18 1969 Honda CL350- $4,000
Bang for your buck, it’s hard to find a better deal than Honda’s CL350. All the years Honda produced the bike (1968-1974) are cake, but the 1969 is the cherry on top. It doesn’t have the birth defects of the ’68 model, but it retains the squared gas tank of the '60s-era Hondas. Of course, the square-vs-round Honda gas tank question is a matter of opinion… but c’mon... look at that thing.
As a “scrambler,” the CL350 sports a higher ground clearance than its brother, the CB350, a reinforced handlebar, and a super slick, chrome-louvered exhaust that tucks up high and tight. That muffler (easily its most identifiable aspect) costs about half the value of the entire bike, FYI.
17 1965 Honda CB77 Super Hawk- $5,000
The CBs and the CLs that followed the CB77 had a hard life. Why? Because the Superhawk was such a demon that its reputation still hasn’t faded away.
With an amazing top speed of 105 mph from a straight twin 350 cc engine, this was Honda’s first foray into the American market.
Even as late as the '60s, post-war America had a hard time swallowing Japan’s take on modern motorcycling. As resistant as they were, though, few American or European bikes could compare when the CB77’s speed, reliability, and price tag were taken together, so its popularity soon skyrocketed.
It’s easy to write this bike off because its styling looks a little dinky by today’s (or any day’s) standards, but that’s precisely why it’s such a beast. With a considerably lighter frame than its competitors, the Superhawk was able to compete with bikes that significantly outclassed its engine size.
16 1974 Norton 850 Commando- $6,000
First off, let’s address the fact that Norton’s 850 Commando might have the coolest name in motorcycle history. And as the name implies, there’s nothing dinky about this bike.
Although small by American (i.e. Harley Davidson) standards, the English Commando’s 850 cc engine was fairly massive when it debuted in 1973. With a 120 mph top speed and enough braking power to ensure that you weren’t destined to smash through the wall of the local pub when tearing down that scenic country road, this bike had it all.
The Commando’s appeal wasn’t limited just to England, however. It proved so popular that it received “Machine of the Year” honors from Motor Cycle News for five consecutive years of its ten-year run.
15 1969 BSA 650 Thunderbolt- $6,200
A lot of people think of these English bikes as interchangeable, but you can say that about a lot of things. If you suggested to those same people that The Who and The Rolling Stones were essentially the same band, they’d probably burn you for heresy.
That said, the BSA 650 Thunderbolt stands out among the other excellent English bikes of its era. It might not be as flashy or as powerful as the 850 Commando, but it wasn’t meant to be.
Although its 46-horsepower engine and relatively light weight make it plenty fast, this bike wasn’t designed to give spectators whiplash.
Rather, its sleek, gentlemanly appearance and accommodating engine design made it the consummate everyday bike. The ability to cruise more than 200 miles between gas stations was a big plus, too.
14 1972 BMW R75/5- $8,000
The R75/5 came in a number of variations, but the one that stands out is the 1972 Short Wheel Base (SWB) Toaster Tank. While its deco-inspired chrome panels harkened back to an era already long gone (which struck potential buyers at the time as a little retrograde), today, it's recognized as the consummate example of 1970s German motorcycle styling.
What the Slash 5 lacked in modern aesthetic, it made up for in incredibly precise engineering. BMW’s iconic opposed-twin engine (a design carried over from its very first motorcycle in 1923!) was so well designed and so well balanced that people were putting hundreds of thousands of miles on their odometers while their American competitors sat in the shop with blown motors.
Super stiff Koni shocks, a shaft-driven rear wheel, and ultra-reliable Bing carbs make this bike a super deal.
13 1963 Vespa 150cc- $3500
Ok fine, it’s not a motorcycle in the strictest sense of the word, but you wanted two wheels, and you wanted cool, and you wanted cheap.
The '50s and '60s Vespas haven’t become undying icons of post-war Italy just because models look incredible straddling them. They’re also incredibly reliable, amazingly easy to service, and use less gas than a Micro-Machine. Oh, and let’s not forget the fact that they’re super cool to look at and so small that they can be stashed in any garage, no matter how many old strollers your wife is forcing you to save.
Considering how beautiful and desirable these little guys are, it’s hard to imagine a solid runner being available for $3,000. But when you consider that Vespa has sold an astonishing 16 million of these babies since their inception in 1946, the math makes a little more sense.
12 1962 Royal Enfield 750 Interceptor- $8,500
Forget the fact that the Royal Enfield Constellation could do 115 mph in 1960; the bike just looked fast. It’s as if the designers stole blueprints from BSA’s headquarters and simply italicized them.
With an aggressive tank shape reminiscent of the Harley Davidson Sportster, a swooped seat that looks built for racing, and low, long exhaust pipes, the bike appears like it's in motion even when resting on its kickstand.
Over the course of its production run (1960 to 1970), the company was constantly retooling it. Some models had different charging systems, some had wet sump oil lubrication, some actually had a 778 cc engine, etc.
It’s a double-edged sword, though. While there are a ton of varieties for collectors and enthusiasts to seek out, limited runs of individual configurations resulted in machining practices that can’t be described as the summit of contemporary international standards.
11 1971 Moto Guzzi Ambassador 750- $10,000
Like any good diplomat, the Ambassador 750 commands respect wherever it goes. In many ways, this stately stead is the opposite of a Royal Enfield. When it’s parked, it looks like it's designed to stay that way; when in motion, it seems like gravity itself is compelling it back to stillness.
At nearly 575 pounds, its 60 horses only propel it to a modest 100 mph top speed.
And while it might not be the swiftest bike on this list, it’s certainly one of the most stylish. With its distinguishable, air-cooled 90-degree twin, chrome valve covers, cigar-shaped exhaust, double-wide seat, and full fender, this bike was the elegant answer to Harley Davidson’s contemporary power-first physique.
Be it because of the styling, the comfort, or the classy name, the Ambassador proved to be a hit. 46,000 units were sold in 1971 alone. If you’re lucky enough to find one today, scoop it up!
10 1955 BSA Goldstar Clubman 500- $10,000
Why would you pay $10,000 for a single-cylinder motorcycle built in the heyday of twins? Because the Clubman 500 is an absolute beast—that’s why. Performance driven in every way, these suckers had a reputation for being one of the fastest, most accessible (that is, affordable) bikes in the 1950s. That meant that anyone with some spare pocket money and even a vague interest in flying down the road at 110 mph wearing nothing but leather goggles could do so.
Each Clubman was handbuilt and factory modifiable and was dyno tested before it ever left the factory floor. So, not only could you jingle the keys under your friend’s nose, but you could also hand him your BSA factory-certified dyno reading to dry his tears of jealousy.
9 1960 Matchless G12- $10750
While not as recognizable a name as some of its brethren, Matchless is one of the oldest producers of motorcycles in English history. When the company opened its doors in 1899, it was fighting for recognition as a bona fide motorized bicycle company. By 1912, it was building its own engines. By 1960, it’d grown so large that it had produced the G12 specifically in order to take a bite out of the lucrative American market.
Designed primarily as a “desert racer” (a defunct term once used similarly to how we now use “dirt bike”), the G12 was built not only to be fast but also to be stable. Its Teledraulic front fork was so effective that racers spread its gospel across the planet, securing its place in motorcycle lore until the end of days.
8 1968 Triumph Tiger Daytona 500- $12,500
Few motorcycle companies have such a storied history as Triumph. Besides their amazing race record and the fact that Marlon Brando famously rode a 1950 Thunderbird 6T in The Wild One, post-war Triumphs simply ooze cool.
Although the Bonneville has historically gotten more press, many enthusiasts prefer the Tiger because of its single (as opposed to the Bonnie’s double) carburetor setup. While the single-carb configuration shed a little off the top end, it significantly increased gas mileage and was much easier to maintain.
For many, this is the bike of bikes–the paradigm of everything incredible and beautiful about life on two wheels. $12,500 will actually get you a museum-quality, perfectly restored specimen.
Since Triumph never truly linked its name with “reliability,” you’re best spending more and getting a goodie.
Buyer, be aware, though, that the pre-1975 Bonnies (like most English bikes) have reversed controls.
7 1976 BMW R90S- $15,000
If you’re buying a BMW R90S and you’re not getting it in Daytona Orange, you’re doing something wrong. Ok, fine... I suppose that’s a judgment call, but the color scheme, as much as the bike itself, has a special place in the chronicles of motorcycle history. The bikini front fairing, fastback tail, and race-inspired color scheme made this baby stick out on the showroom floor.
Although all of the BMWs of that era boasted rock-solid engineering, the R90 engine is commonly agreed to be the best. With the perfect amount of power, a lighter dry weight than its big brother, the R100, and superior balance and handling, this is a bike that no one outgrows. It’s with renewed glee that you fire it up and listen to the distinctive “airhead” valve clatter.
These bikes are rapidly growing in value, perhaps because less than 17,500 were produced during its short run (1973-76) but maybe just because they’re the pinnacle of cool.
6 1948 Harley Davidson WL 45- $15,000
The value of these old flatheads varies wildly. While a matching-numbers, low-miles, original paint stunner might run you north of $30,000 dollars, you can get a more-than-decent runner for half that.
The WL 45 gained its reputation during World War II, when its military variant, the WLA, saw action all over the world.
After the war, the US government had so many of these things on its hands that it dumped them on the civilian population for a pittance. In an effort to push them to their limits (by removing elements like their impossibly heavy sheet-metal fenders), post-war Americans essentially created chopper culture then and there.
Mind you: this is a bike from a different era. Most frequently configured with a solo seat, always sporting a tank shift and toe-heel clutch, and completely devoid of a rear suspension, this isn't a bike for the faint of heart.
5 1964 BMW R60/2 with Steib Sidecar- $17,000
In the same way that the BMW R75/5 Toaster (#7 on this list) was viewed as old-fashioned, even at its debut, the R60/2 was also an anachronism. Produced all the way until 1969, no other major manufacturer but BMW held onto the rounded-fender, fin-style tail light look for so long.
And while it might not have looked old-timey back then, it sure as heck does today. But that’s exactly the point. Rather than buying a bike like a 1940s Harley Davidson, you might consider buying a much newer, technologically superior bike that boasts similar aesthetic highlights.
There’s no need to add the Steib sidecar, but why wouldn’t you? Between the R60/2's beautiful belly and the Steib sidecar’s memorizing lines, you and your companion (dog?) couldn’t help but look like eccentric millionaires. Oh yeah... and for less than 20 grand.
4 1958 Harley Davidson FLH- $20,000
The FL model Harley Davidsons entered production in 1941, and iterations of them are still being built today. But in 1958, the company released its first-ever Duo-Glide, which boasted some serious improvements over its predecessors.
Pre-1958, almost every bike produced in the world lacked a rear shock absorber, meaning the only cushion between your spine and any microscopic bump in the road was a single small (largely ineffective) spring under the seat. The Duo-Glide changed this. Hydraulic front forks (taken from the earlier Hydra-Glide models) coupled with a newly designed rear-swing arm with coil over shocks meant riders could now take their bikes on day-long journeys without causing lasting damage to their central nervous systems.
Another advantage was the recent addition of the Harley Davidson Panhead engine, which increased power, increased cooling efficiency, and reduced weight over the earlier Knuckleheads.
3 1975 Harley-Davidson XR750- $22,000
While we’re on the topic of all-star American machines, how about one of the most iconic Harley Davidsons ever produced? Most people equate Harleys either with comfy cruisers or gleaming chrome pipes, but the company has actually produced a range of bikes throughout its history, and this bona fide track bike is one of them.
The XL750 has had a long run (born in 1970 and still being produced today), but its early years were its most famous, specifically 1970-76. Why, you ask? Only because a certain fantastic, flying, death-defying demon named "Evil Kenevil" performed some of the most memorable feats in two-wheeled history on it.
Seeing the XL750 cross canyon gaps or fly over entire fleets of school buses was how many Americans got their first mainstream access to motorcycle culture. Boys across the country emulated him (painfully, we might assume) on their bicycles, dreaming of the day they would have their very own XR750s.
2 1941 Indian Chief- $23,000
Every time I see this machine, I fight the urge to sing a tearful rendition of the National Anthem. Maybe it’s the swooped fenders that recall dusty Midwest plains, or maybe it’s the ubiquitously fringed cowboy saddle, but something about this bike screams “America the Beautiful.”
Back in pre-war America, Harley Davidson and Indian duked it out harder than Rocky Marciano and Jersey Joe Walcott. While Harley Davidson ultimately won in a unanimous decision, it wasn’t always clear who the victor would be. After all, in the 1910s, Indian was the largest motorcycle manufacturer in the world.
What it boiled down to was the fact that Harley Davidson got more and better war contracts than its competitor. By 1945, Indian was sold to a conglomerate that stripped it of its essence.
But the 1941 Indian Chief was the absolute summit of the company’s engineering and aesthetic.
1 1977 Ducati 900SS- $40,000
Significantly more expensive than some of the other bikes on this list, the Ducati 900SS is really in a class of its own. As one of the first true “super sport” bikes (hence the SS), this machine would set the tone for all future Ducatis. Light, agile, and awesome to look at, the 900SS is a masterpiece.
Just look at the way the bikini front fairing appears to be stretched over the headlight by sheer velocity. Its proportions are remarkable. Every little design element accentuates a separate part of the bike, drawing your attention elsewhere. It’s nearly impossible to keep the eye from darting from one flawless design element to another.
If Speed Racer rode bikes, this would be the one he chose; if Salvador Dalí dropped acid and was asked to draw a motorcycle, this is what he’d hand you.