9 Of The Best-Looking Harley-Davidson Softails Ever Made

Some people think Harley-Davidson sticks to outdated designs and power units, despite the fact that Harley-Davidson is constantly upgrading its engines and look. However, we argue that you don't need to mess with perfection, as can clearly be seen in the iconic designs of some Harley-Davidsons. 

Before we dive into our look at some of the company's best looking bikes, however, let's quickly run through what the word softail means. In the biking community — that includes both motorcycles and bicycles — a hardtail model is one that has suspension units only at the front, not at the back. Hence, when going over a road bump, only the front wheel will have an impact absorption factor, and the rear wheel will remain hard, hence the name — hardtail. 

A softail, on the other hand, will have suspension units both at the front and the rear, providing a far more comfortable ride on long journeys. Many of the best Harley-Davidson Softails take the concept one step further, though, as most Harley Softail hides the rear suspension beneath bag carriers, fenders, or other performance paraphernalia on the rear. This gives Harley riders the best of both worlds — the clean, sleek looks of a hardtail bike, as well as the much-desired comfort of a softail. 

With that in mind, not all Harley-Davidson Softails are made the same — some are much better-looking than others. Here are 12 of the best looking Harley-Davidson Softails ever built.

The FXDR-114 is undoubtedly among the most stylish Harley-Davidson motorcycles ever designed. It has a 120mm tire at the front, and double that on the back — a 240mm wide tire mounted on an 18-inch wheel, making for a supremely comfortable riding experience. It is definitely oriented towards performance and shorter-distance tours, and the riding position reflects that, with riders having to bend forward to reach the handlebars. 

Between said handlebars is an LCD screen — yes, this Harley has a fully digital dashboard, even replete with a digital speedometer. For some purists, having anything digital on a bike is a slap in the face to Harley-Davidson's legacy, but then again, the FXDR was supposed to capture a younger market with its funky colors, aggressive styling, and most importantly, stellar performance. 

It just so happens that the FXDR-114 is also one of the most affordable Harley-Davidsons (that are not a decade and a half old) currently on the used market, with decent examples in the $10,000 to $14,000 range. It is also worth noting that the FXDR-114 came with one of the most powerful engine ever put in a Harley-Davidson Softail motorcycle – a Milwaukee-Eight 114 unit in the classic V-Twin layout that pushed out an eye-watering 119 lb-ft of torque. 

Remember, that torque was for a motorcycle that weighed 637 pounds – not exactly light, but a far cry from the heaviest Harleys. All in all with its flowing lines, chrome or gold accents, and matte finishing, the FXDR-114 is definitely a looker.

Next is the Heritage Softail Classic. Our focus here is specifically on the Shrine edition, which was a limited-edition run that arrived in two exclusive colors — Arctic White and Concord Purple — and with a special steel badge. 

What you got in this package was a classic Harley cruiser but with all the updated tech that you'd ever want. It looks a lot like one of the classic long distance cruisers from the '60s, with chrome accenting on everything from the wheels and fork to the engine and exhaust. The chrome accents on the wheels — especially when polished to a shine — gave the effect of whitewall tires, further adding to the screaming '60s look. Buyers also got a two-step seat, with the passenger seat being raised above the rider with its own backrest, along with genuine leather saddlebags to match. 

While the Shrine edition got the best colorways, another one we should mention is the 110th Anniversary edition. While largely the same, this version came with actual whitewall tires, making it a real piece of eye candy. Power for these gorgeous machines came from the 1,690cc, 97 lb-ft Twin Cam 103, which was an iterative upgrade from the legendary Twin Cam 88 and Twin Cam 96 engines that came before it. The 110th anniversary edition also got ABS and Harley's smart security system as standard, where other models had to opt in for the Security Package to get them.

Next up we have the Softail Slim. If Captain America were forced to choose only one bike to ride for the rest of his life, it would probably be this one. At the root of it, the Slim is a bobber bike that is surprisingly practical as a city runabout, and by all reports is a fantastic heavier bike for experienced and beginner riders alike.

The Softail Slim features a 107 cubic inch (1,746cc) Milwaukee-Eight V-twin engine, making 110 lb-ft of torque with 73 hp and getting an estimated economy of 47 mpg. The 2021 model year added three gorgeous new colorways, namely River Rock Gray over Black Denim, Midnight Crimson over Stone Washed White Pearl, and Billiards Red. 

Of course, the original paint scheme of vivid black is still available, and doesn't cost you anything extra — the price for the 2021 Softail Slim starts at $15,999 but can go all the way up to $16,749 depending on which color swatch you choose. An interesting feature on this model year is the digital-analog dashboard — the speedometer is analog, but everything else like the odometer, trip details, fuel gauge, and range indication are all digital.

The Deluxe is not just one of the best looking Harley Softails — it's one of the best looking motorcycles ever made. It comes with the same Milwaukee-Eight V-Twin 107 cubic-inch engine that the Softail Slim from earlier is rocking, although it makes a little more torque. It's not a small bike either — at nearly eight feet long, the Deluxe weighs 668 pounds and rides on 16-inch chrome-plated wheels. 

In addition, the Softail Deluxe is much better suited for long-distance cruising than other Harley Softails, given its five-gallon fuel capacity, where the Softail Standard has a 3.5-gallon tank. With an estimated economy of 47 mpg, you should be getting about 225 miles between fill-ups. 

The Softail Deluxe also gets a redesigned exhaust system, new and much-improved front fork, and modern rider-friendly features like three-unit LED lighting, an ABS system and active counterbalances. In terms of design, the fenders are perfectly positioned to accentuate the whitewall tires that come standard on the bike, and there is chrome just everywhere — on the engine, on the exhaust pipes, on the headlight, and even on the side mirrors. 

However, it doesn't feel like the chrome has been tackily slapped on or overdone — it's just the right amount. If you saw one of these bad boys on the road, you can bet the house that you'd be giving it a second look.

With a name like Cross Bones, you already know that this bike is going to be an absolute stunner . You can tell that Harley-Davidson have gone above and beyond for this one, with a hand-stitched, sprung leather seat that has enough padding on it to feel like a mattress. The rubber-topped footrests and pedals are also plenty comfortable, and the distinctive front end — called a Springer — melts away beautifully into the headlight units. The Cross Bones is the first real tourer on our list, as evidenced by the seating position which keeps your back nearly straight and the handlebars that come up almost to shoulder height.

Given the lack of a stock windscreen on the Cross Bones, buyers are definitely advised to opt for either an OEM Harley or aftermarket windscreen, especially if this bike is going to be for longer jaunts. Power comes from the Twin Cam 96 that we mentioned earlier, making 93 lb-ft of torque — all of which it needs given that it weighs 700 pounds. Credit where credit is due though, the bike manages an impressive 35 mpg in the city and 54 mpg on the freeway, despite its mammoth weight. Overall, it has a very distinctive look, and is one of Harley-Davidson's most underrated bikes — possibly of all time.

We already covered the Heritage Softail Classic above, but this special edition deserves its own spot on our list — plus it actually came out before the Shrine and 110th anniversary unit. 

The Firefighter Special Edition ran from 2007 through to 2008 and was only available at the time to current or retired firemen. It also came with the standard Softail engine at the time, the 1,584cc Twin Cam 96B that would later become the inspiration behind the Twin-Cam 103 found in the 2013 Heritage Softail Classic models. As mentioned, this engine could produce 119 lb-ft of torque and was paired to a manual six-speed Cruise Drive gearbox. 

As with most other Softails, it got those beautiful rear chrome-laced steel wheels that had the added benefit of not rusting. Additional design talking points were the staggered shorty dual pipe chrome-plated exhaust system, front fender running lights, special badge on the fuel tank and the detachable king-size windshield. As for color options, there was only one — fire engine red everything, of course.

The Rocker C is a Harley-Davidson motorcycle in a staggeringly unapologetic way. It's loud, but we're not talking about just the 1,584 cc and Twin Cam 96 engine, which is plenty loud already. At the front you have a low-profile 90mm slim tire, and at the back is a gargantuan 240mm wide rear tire, both mounted on cast aluminum five-spoke wheels. Also made out of cast aluminum is the massive oil tank, replete with fins for added aerodynamics as well as cool points. 

Also, it is one of the few options on our list that does not come with whitewall tires, though we'd say there's considerable argument for using them anyway — it just looks too good. The attention to detail with the 2010 Rocker C's design is simply mind boggling. It features a concealed pillion seat to not spoil the silhouette, as well as a color-matched swingarm, frame, subchassis, and oil tank to boot. If bikes could be hot rods, then the Rocker C would definitely be one of those long black ones with a supercharger and flames painted on the side. 

There's not much more to be said — it's a powerful bike that turns heads wherever it goes, and is a Softail, so it makes our list.

The second-last bike on our list of the best-looking Harley Davidson Softails is another special edition — this time, the 105th Anniversary Special Commemorative Edition Softail Classic. It came in a very specific colorway called Copper Pearl and Vivid Black, which worked together quite well and lent itself to a sort of "Mad Max" vibe, but in a very subtle and refined way. If you can call any Harley subtle, that is. 

Like its non-commemorative 2008 sibling, the regular Softail classic, you got chrome on all the important and visible bits, like the engine, dual shorty exhausts, front fork, the beautiful spoked wheels, and even behind the passenger backrest — talk about going the extra mile. 

You also got copper-colored accents on the rear mud flap, the engine cover, the oil cap, and at several other visible places on this piece of automotive art. It also was powered by the trusty Twin Cam 96 workhorse, outputting similar performance numbers to the other Softail Classics on our list. All in all, it's a breath of nostalgia, for riders who want to relive the glory days with a two-tone paint job, studded genuine leather saddle bag, massive windshield, and full-flared front fender — truly befitting of a bike made to commemorate more than century of Milwaukee House's dedication to riding.

To top things off, let's look at the 2005 Harley-Davidson Night train, a sleek, refined, no-nonsense road bike. Officially named the Harley-Davidson FXSTB Night Train, this model ran from 1998 all the way through 2010. 

Starting at the front, we get a single headlight, unlike the three lights on other Softails, and the super skinny tire and wheel are set a little more forward than usual. In typical Harley-Davidson styling, the dashboard instruments are located just above the fuel tank opening, which itself leads down to the padded leather seat, with the pillion being higher than the rider. 

Below that is the familiar 1,584cc Twin Cam 96B engine in a V-Twin layout. In an industry-shaking specification for the time, all later-generation Night Train models came standard with front-oriented foot controls, a cast aluminum wheel at the back, chrome-steel laced wheel at the front, bobtail fenders, and a powder coated engine. You also got the chance to choose from textured black or wrinkle black engine covers. 

With its sleek chrome-plated dual-shorty exhausts, chrome bottom half, and all black top half, this is the bike that Batman would have chosen.