Like a lot of the clothing guys wear today, the leather jacket got its start as a utilitarian object. There was no need for a bomber jacket, a motorcycle jacket or a racing jacket before the inventions of the airplane, the motorcycle or the automobile.

But leather jackets didn’t make their widespread style debut until after World War II, when the idea of leather for style, instead of purely for function, started seeping into popular culture.

After sky-rocketing to popularity by way of Marlon Brando in the film The Wild One, the motorcycle jacket became such a symbol of youth in revolt that it was banned in schools for an entire year in the mid-1950s. And this helped place them on the backs of guys who wanted to telegraph rebel cool, gaining popularity throughout the 60s, 70s, and 80s.

“[For] everybody from Elvis to The Beatles, to The Stones, every psychedelic band from the Jefferson Airplane to the Grateful Dead, it was like a rite of passage,” said Michael Paradise, a former employee of North Beach Leathers who now owns The Stronghold, a heritage clothing boutique in Los Angeles. “You signed a recording contract, you got your first paycheck, you went to North Beach Leather.”

They’re now an indispensable part of a man’s wardrobe — and guys who work in more casual settings can get away with swapping a minimal black, brown or navy leather jacket for a blazer. It’s more durable, water repellent, and looks just as good over jeans as it does with a pair of tailored trousers.

With so many options on the market, finding the perfect one for you can take a lot of time and research — and it’s worth taking your time. Because unlike other clothing, buying a leather jacket is like buying a piece of furniture. Pick the right version and you’ll have it for years to come. Go with the wrong thing, and you might end up making an expensive mistake.

To help shorten your list of candidates, we compiled our favorites across four major categories. We also spoke with experts about style, fit, quality and care to help inform your purchase. Here are our recommendations, from the save-a-little level to splurges that might break the bank, and a guide to making sure your newest style investment lasts a lifetime.

Motorcycle Jackets

The classic motorcycle jacket is an immediate marker of rebel cool. In fact, it’s been used in so many movies and TV shows as shorthand for “bad boy” that it should be a tiresome cliché at this point — and yet its magic still works. Throw one on and you’ll immediately embody the rugged charm and sex appeal of every style icon of the last several decades. The best thing about a biker jacket, providing you get one worth its skin, is that it keeps getting better with age.

Allsaints Estello Leather Biker Jacket

Made from soft, lightweight lambskin, the Estello biker jacket is a true multi-season must have. Because it’s so soft it drapes and forms to your body almost immediately. Its quilted detailing makes it a great choice for any guy who wants to wear his jealther jacket with a t-shirt in cool weather.

Schott Perfecto Slim-Fit Leather Biker Jacket

The original American motorcycle jacket is still in production 90 years after its invention. So if authenticity and legitimacy are important to you, this is the jacket to get. And because it’s cut from such thick leather, it’s also your best choice if you’re actually going to ride a motorcycle.

John Elliott Slim-Fit Leather Biker Jacket

You may know John Elliott for his eponymous streetwear line, but that’s far from where his talent ends. This Mr. Porter exclusive has lots of sharp-looking bells and whistles: three front zipper pockets, nickel snaps, epaulets, and zippered cuffs. It’s also fully lined to keep you warm (but not too warm).

Bomber Jackets

Originally worn by Air Force pilots to keep warm at high altitudes, the leather bomber jacket has come a long way from its pragmatic beginnings. But for the most part, its design has stayed true its roots.

Today, it’s among the most popular menswear items on the market thanks to male celebrities who rely on it to make them look well-dressed, but not dressed up and cool but not too edgy. “It’s a safe bet, like a pair of jeans,” says Jeanne Yang, stylist to a list of guys that includes John Cho, Alexander Skarsgaard and Robert Downey, Jr., among others. “If you’re gonna spend the money, it’s something you know you can keep on rotation in your closet.”

The Arrivals Ford Leather Bomber Jacket

A slimmer, more fashionable take on Indiana Jones’s famous rig. The Arrivals is known for high-quality products at beginner-level prices—and they come with a lifetime warranty. This model is also pre-treated to protect it against water and stains.

Golden Bear Black Zip Front Baseball Jacket

Golden Bear has been crafting quality leather jackets since 1922, originally serving dockworkers lugging cargo out of San Francisco Bay. This baseball-style bomber will still stand up to heavy work and harsh climates, so it can handle your morning commute without a problem.

Mr P. Leather Bomber Jacket

If you’re looking for something that isn’t all black, your next best option is navy blue. This model is just as versatile as a black version, but it’ll also ensure you don’t show up to work wearing the same jacket as your cubicle mate.

Racing Jackets

If you’ve ever watched Easy Rider or seen a photo of Keanu Reeves, you know that leather racing jackets aren’t meant for kids. The collarless gems have all the testosterone of a motorcycle jacket — but none of the 1950s Danny Zucko theatrics. Plus, they come in a wide array of styles from pared-down suede numbers to more souped-up versions with quilted shoulders and elbows.

Reiss Jacob Suede Jacket in Navy

If you’re into the design of a racing jacket but looking for something a little softer, this is the one for you.. Made of supple navy blue suede Reiss’s Jacob jacket pairs exceedingly well with a pair of your fanciest work trousers.

Lewis Leathers Racing Jacket No. 442

Lewis Leathers has been outfitting men in leather since 1892. That’s plenty of time to perfect every last detail. Their racing jacket features quilted and padded shoulder and elbow patches, four pockets and adjustable straps at the waist. Each Lewis Leathers jacket is made to your specific body measurements, making it well worth the price.

Sandro Leather Jacket with Quilted Trims

Sandro’s take on the leather racing jacket embodies the best of both luxurious materials and streamlined design. Its tough quilted shoulders are crafted from buttery lambskin, and the gusseted sides make for a slim yet comfortable fit.

Shearling Jackets

Shearling (the skin and fur of a sheep) is nature’s warmest material. Because of that, most jackets cut from it can lean toward the higher side of the price spectrum. They can also be tough for some guys to pull off.

“Shearling is a great look but you have to find the proper fit for you,” says Donnell Baldwin, a New York-based menswear stylist. “Many shearling jackets are long and could be ‘a lot of look’ for a shorter guy. If that’s you, you’ll need to find a short version that complements your height and style.”

Spending upwards of $2,000 on a shearling jacket that you can hand down to the next generation isn’t any more frivolous than investing in a luxurious watch. Here are three worth saving for.

Isabel Marant Anders Shearling-Lined Leather Jacket

The rich caramel brown color of this Isabel Marant shearling jacket is a refreshing swap for the classic tan and beige you’ll see everywhere this winter.

RRL Slim-Fit Shearling Jacket

Inspired by the bomber jackets worn by American pilots in the 40s, this RRL shearling is a menswear nerd’s holy grail. Two envelope patch pockets, waist tabs, and a buttoned throat latch are the kind of artfully designed details we’ve come to expect from the brand.

Dunhill Shearling Leather Jacket

Dunhill, the brand that pivoted from saddle design to luxury clothing and accessories in 1893, is still wowing us today. And this made-in-Italy number is no exception. If you’re able to drop this kind of dough we think it should be spent on something with a significant history and a construction that’ll last for years to come.

5 Tips for Taking Good Care of Your Leather Jacket

This is the part where we tell you not to throw an investment-level jacket on a pile of clothes — or worse, the floor — after each time you wear it. Your new jacket deserves proper care, and luckily that’s pretty easy to deliver. We asked David Mesquita, co-owner and vice president of Leather Spa, how to give your jacket its best life possible.

An Ounce of Prevention

“Leather is just like our skin, we put moisturizer on in the winter because our skin gets dry. It’s the same with the leather jackets. As you’re wearing it, rubbing up against stuff, the natural oils in the skin are gonna wear out,” Mesquita says.

Leather Conditioner by Leather Spa $13

Before you wear a new leather jacket the first time, spray your jacket with water and stain protector, especially if it’s made of suede. Then at least once a season, you’ll want to condition your jacket to keep the leather from drying out. “If it’s something you wear often, you might have to do a conditioning in the middle of the season versus waiting till the end,” he added. “A good rule of thumb is you can always look at the jacket and you start to see some fading. That could be a sign of it drying out and you should apply some moisturizer.”

But fair warning: it may darken the color of your jacket. If you’re not sure how much to use or nervous about application, ask a professional.

Give it Some Space

There’s nothing wrong with storing your jacket in the back of your closet during the offseason. But you want to make sure it has room to breathe and hang naturally. Don’t cram it into an overcrowded closet or store it folded under heavy coats and sweaters. Marks from creases and folds can’t be ironed out of leather the way they can with other fabrics. So you want to avoid any undue pressure for long periods of time. To keep your jacket next-level fresh, consider keeping a box of baking soda or a sachet of cedar chips in your closet.

Hang Tight

Never hang your leather jacket on wire or thin hangers. Instead, spend some money on wooden hangers with adequate shoulder support.

“I wouldn’t let it sit on one of those thin hangers for too long because it stretches the shoulders out and leaves that imprint,” Mesquita said. “The best way to store leather items is in the fabric garment bag you get when you purchase the jacket because they’re breathable. God forbid you have your jacket in a storage unit and there’s some type of humidity or moisture that gets trapped in there.”

Clean it Fast

Spilled beer, motorcycle grease and other kinds of dirt are going to happen. But don’t let stains sit for more than an hour or two, or they’ll require professional cleaning.

“If you get a stain on it or a mark, you want to treat it right away before it penetrates into the pores of the skin and becomes permanent like a tattoo,” Mesquita says. “The best time for any type of care is when you get home just before putting it away in your closet. Look it over, and if you see a little spot or a blemish just rub it right off before it becomes permanent. Or use a little bit of a spot cleaner and then just rub it right off.”

Know When to Go Pro

For anything more intense than a spilled beer or a spot of dirt go straight to a pro. Trying to fix something without the proper training could just lead you down a path to more trouble. Put simply, “If its a jacket that you spent a lot of money on, you’re better off taking it to a professional,” Mesquita says.

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