10 Best Men’s Leather Jackets Under $500

There aren’t a whole lot of items of clothing that you could, with a straight face, call ‘heritage pieces’. Clothes, for better or worse, have short lifespans. Leather jackets, however, are a bit of an outlier.

These jackets, first developed to be rugged enough to hold up to the demands of asphalt, high winds, and hot lead, are tough enough to stick around for much, much longer than your common t-shirt or even field jacket. As a result, consumers are more willing to open their wallet and shell out a few extra clams for a solid leather jacket. Yet, with that being said, one doesn’t have to go broke just to slip one of these jackets on. There aren’t a whole lot of leather jackets under $500, so we scoured the web to pull together what we think are some of the best so you won’t have to spend all of your precious time doing the same.

The History Of The Leather Jacket

Born Above The Battlefield

The leather jacket’s reputation of being – for lack of a better term – a “tough-guy’s” garment, isn’t some recent development hastened by savvy advertisers and marketers. From their inception leather jackets have been built for wearing in demanding and tough environments.

Like most all popular items in a man’s wardrobe, the leather jacket got its start on the battlefield (or maybe more accurately – above it). In the early 1900s, the Luftstreitkrafte – an early version of the German air force – were looking for tough, warm jackets that would stand up to the high wind and low temperatures experienced in those early warplanes. The wind and abrasion resistant qualities of tanned cow hide proved to be the perfect solution. Those flight jackets would soon be ubiquitous both on the German front, and eventually during the Second World War they’d be adopted by Allied forces as well.

But even in the early 20th century the military didn’t have a monopoly on leather jackets. In around 1928, a Harley-Davidson distributer in the U.S. by the name of Beck Industries ordered up a batch of jackets with the same qualities as those early German airmen required; weather and abrasion resistance. The result was the Perfecto Leather jacket – that exposed metallic zipper and snap-button motorcycle masterpiece we still see around today.

Today, the leather jacket appears in a number of different forms. Head to H&M or Uniqlo and you’ll find plenty of faux-leather examples that feature the look, but the none of the original toughness. Go to more high-end men’s stores and you’ll see pristine examples alongside pre-distressed ones. Whatever the style or model – each finds its own way of channeling that heritage toughness that made them so popular in the first place.

Selected Homme Leather Biker Jacket

The leather jacket isn’t immune to changing styles. While the piece may have started out with a bulkier cut, in more recent history there we’ve seen more examples of the piece with a much closer fit. This pick from Selected Homme is a perfect example of exactly this more contemporary style of leather jacket. Featuring a midweight leather outer material fitted with a zip fastening and snap collar, it boasts an attractive look and fit that’ll last year in and year out.

Purchase: $332

Massimo Dutti Nappa Jacket

An attractive, simple example from Massimo Dutti. This jacket is made from a high-end sheepskin leather that features a close fit, a front zipper that goes all the way up to the snap-fastening collar, and two zippers along the cuffs. The interior is made from a combination of polyester, viscous, and cotton and has a series of inside pockets. A great pick for under $500

Purchase: $345

Alpha Industries MA-1 Leather Flight Bomber Jacket

If it is the old-school WWII flyboy look you’re going for, this jacket deserves a second look. Cut like your typical bomber jacket but featuring a pure leather exterior, it is close to the spitting image of what so many airmen wore during the 1940s. The jacket boasts a cigarette pocket on the left sleeve, snap-button pockets along the waist, and a rib-knit collar, cuffs, and waistband.

Purchase: $346

Vanquish Lamb Nappa Leather Jacket

Simple looks are sometimes the hardest to do. Ryo Ishikawa’s Vanquish, however, seems to flawlessly execute the paired-down minimalist look no matter what. Take for instance their Vanquish Lamb Nappa Leather Jacket. This piece, now set for under $500, boasts a black leather look with contrasting silver zippers and snap-button closure along the neck.

Purchase: $350

L.L. Bean Flying Tiger Jacket

Another more classically styled pick from L.L. Bean. This leather jacket features a goatskin exterior, a combination of merino wool and polyester pile for lining, and thinsulate in the sleeves. This lining and exterior combined with the snap-down collar makes the coat an ideal one for wearing during the colder months.

Purchase: $380

Blank NYC Black Out Jacket

While this pick from Blank NYC features a more tailored fit like others previously on the list, it takes a decidedly different approach when it comes to the collar. Rather than going for the snap button along the neck, it features a rib-knit collar like you’d find on a bomber jacket. It’s a slight change in styling, but it goes a long way.

Purchase: $398

Buck Mason Bruiser Moto Jacket

Styled after the original leather motorcycle jacket, this piece from Buck Mason channels all of the old-school cool of the original while giving it a slightly contemporary take. Featuring a more tailored fit, this jacket with its metallic hardware sits close to the body and exudes an enduring cool vibe thanks to its carefully cut lambskin leather outer material. A pick that’ll be sure to last a lifetime.

Purchase: $495

Golden Bear Virgin Wool-Blend Leather Bomber Jacket

Admittedly, this is not a ‘leather jacket’ in the traditional sense. The only leather thing about it is its sleeves and welt pockets – but given how well built this piece is, we couldn’t help but include it anyway. A more mature version of the varsity jacket, this thing features a body mode from a virgin wool-blend, a rib-knit waist, collar, and sleeves as well as an attractive set of snap-buttons down he front. A great grab for those looking to go for a more classic American route.

Purchase: $495

Allsaints Lark Leather Jacket

Rather than going for that high-contrast metallic-zipper-on-black-leather look, the Lark Leather jacket from Allsaints instead opts for a black-on-black color way. The result is an attractive, understated pick ideal for wearing either on the weekends or in the office.

Purchase: $498

Scotch & Soda Lightweight Leather Jacket

Few things are better than a well broken in item of clothing. Whether it be a shirt, a pair of jeans – there is just something about throwing on something that feels soft and lived-in that is hard to beat. The folks at Scotch and Soda understood as much, which is why they developed this lived-in lightweight leather jacket. Made from a cowskin leather with a washed look and a shit jacket cut, it drapes over the shoulders in a comfortable, casual manner that makes it perfect for everyday wear.

Purchase: $498

8 Best Leather Motorcycle Jackets

There are leather jackets out there that do a whole lot more than just make you look cool. Leather motorcycle jackets, for instance, will go a long way towards keeping you safe both in and out of the saddle.

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