Getting a Good Leather Jacket
Once you become interested in clothes, it’s not hard to buy more than you need. In the past two years or so, I’ve acquired eight leather jackets. Most get worn on some semi-regular basis (OK, semi-semi-regular), but none get broken out as much as this leather A-2 you see above. In fact, I could get rid of all my other casual jackets and be satisfied with wearing just this one. 
When shopping for a leather jacket, I’ve found it’s good to pay attention to a few factors:
Materials: Most leather jackets are made from lambskin, goatskin, cowhide, or horsehide. Generally speaking, the first two will be lighter and thinner than the second two. Lambskin is exceptionally soft, pliable, and comfortable to wear, but it’s also most prone to tearing. Goatskin is a bit tougher and more pebbled in its texture. Neither, however, is as tough as cowhide or horsehide, which might require a circular saw to break open. The tradeoff is that cowhide and horsehide are very stiff and heavy, though that might suit certain styles more. It all depends on what you want out your garment and how you want it to look. Want something to wear to an overheated wine bar? Lambskin is a great material. Want something to fight a bear in? Cowhide and horsehide are good bets.
Insulation: Like with all garments, leather jackets are often made with seasons in mind. Spring/ summer pieces often have thin, breathable linings, or on rare occasions, they may come without any lining at all. Fall/ winter jackets, on the other hand, are often quilted or insulated. If you live in a temperate climate, like me, it may be good to err on the spring/ summer side, as you can always layer with a piece of knitwear. My A-2 pictured above, for example, has unique, open-weave cotton lining, and for cold days, I just pair it with a grey sweatshirt. 
Style and color: I hesitate to recommend a style or color, as that gets into such subjective territory. You should just get what you like best. That said, I find myself wearing mid- to darkish browns most, and tans least. And from the few leather jacket threads I follow on various clothing forums, it seems that many men get a lot of use out of their A-2s. Whether that style suits you, of course, is a personal call.
It may be important, however, to think of leather jackets not just in terms of their most basic styles (e.g. A-1s, A-2s, motos, etc.), but also their sensibility. An A-1 from a luxury fashion house, for example, will look very different than one from a vintage reproduction company. Just compare this Ralph Lauren Purple Label piece to something similar from Good Wear Leather to see what I mean. It’s not just a difference in materials (a “luxury” piece will often be made from a fine lambskin, while a tougher, “authentic” version will be made from goatskin or horsehide), but also a difference in the cut and detailing. When shopping for a jacket, pay attention to these differences, and think about what kind of clothes you’ll be wearing your new jacket with. Maybe you want something from a very avant garde designer, or luxury Italian label, or a workwear company. That choice alone should narrow the field considerably. 

Getting a Good Leather Jacket

Once you become interested in clothes, it’s not hard to buy more than you need. In the past two years or so, I’ve acquired eight leather jackets. Most get worn on some semi-regular basis (OK, semi-semi-regular), but none get broken out as much as this leather A-2 you see above. In fact, I could get rid of all my other casual jackets and be satisfied with wearing just this one. 

When shopping for a leather jacket, I’ve found it’s good to pay attention to a few factors:

Materials: Most leather jackets are made from lambskin, goatskin, cowhide, or horsehide. Generally speaking, the first two will be lighter and thinner than the second two. Lambskin is exceptionally soft, pliable, and comfortable to wear, but it’s also most prone to tearing. Goatskin is a bit tougher and more pebbled in its texture. Neither, however, is as tough as cowhide or horsehide, which might require a circular saw to break open. The tradeoff is that cowhide and horsehide are very stiff and heavy, though that might suit certain styles more. It all depends on what you want out your garment and how you want it to look. Want something to wear to an overheated wine bar? Lambskin is a great material. Want something to fight a bear in? Cowhide and horsehide are good bets.

Insulation: Like with all garments, leather jackets are often made with seasons in mind. Spring/ summer pieces often have thin, breathable linings, or on rare occasions, they may come without any lining at all. Fall/ winter jackets, on the other hand, are often quilted or insulated. If you live in a temperate climate, like me, it may be good to err on the spring/ summer side, as you can always layer with a piece of knitwear. My A-2 pictured above, for example, has unique, open-weave cotton lining, and for cold days, I just pair it with a grey sweatshirt. 

Style and color: I hesitate to recommend a style or color, as that gets into such subjective territory. You should just get what you like best. That said, I find myself wearing mid- to darkish browns most, and tans least. And from the few leather jacket threads I follow on various clothing forums, it seems that many men get a lot of use out of their A-2s. Whether that style suits you, of course, is a personal call.

It may be important, however, to think of leather jackets not just in terms of their most basic styles (e.g. A-1s, A-2s, motos, etc.), but also their sensibility. An A-1 from a luxury fashion house, for example, will look very different than one from a vintage reproduction company. Just compare this Ralph Lauren Purple Label piece to something similar from Good Wear Leather to see what I mean. It’s not just a difference in materials (a “luxury” piece will often be made from a fine lambskin, while a tougher, “authentic” version will be made from goatskin or horsehide), but also a difference in the cut and detailing. When shopping for a jacket, pay attention to these differences, and think about what kind of clothes you’ll be wearing your new jacket with. Maybe you want something from a very avant garde designer, or luxury Italian label, or a workwear company. That choice alone should narrow the field considerably. 

The Simplest Casual Look
Although I enjoy wearing tailored clothes on weekdays, I dress pretty casually on weekends. Lately, that’s meant dark blue jeans with a clean white t-shirt and a nice, brown leather jacket. For shoes, I wear either sneakers or boots, and if it’s cold outside, I layer with a heathered grey sweatshirt. I find it’s one of the simplest, easiest looks you can put together, and depending on your lifestyle, very well suited to casual weekend activities with friends.
For jeans, I really like 3sixteen’s SL-100x model. It’s a slim straight-legged cut made from a medium-weight selvedge denim that doesn’t bag as easily as other brands’. I’ve also been admiring their premium 3sixteen+ line, as well as Flat Heads 3009s and Iron Heart 634s. Those are made from unsanforized denim, which Kiya at Self Edge tells us will yield more interesting fades over time (without the need to forgo washing, thankfully). For something more affordable, check out Albam, Gustin, and Uniqlo’s Made in Japan offerings.
For the t-shirt, I stick to a pretty basic Hanes’ Beefy-T (I get the one with a chest pocket). It has a stoutness that I think works well with this kind of look, and it can be easily found on sale for about $6. Jesse has also recommended Costco’s Kirkland t-shirts for this sort of thing. For something thinner and stretchier, check out Alternative Apparel, which Jesse does bulk orders on every summer, and American Apparel. Levis also has a nice model that’s in between the toughness of Hanes and the fineness of the last two brands.
Finally, there’s the leather jacket. These can get astoundingly expensive, but it’s worth buying the best you can afford. Just as you can get away with a pair of cheap chinos and dress shirt if you have a really nice fitting sport coat, you can skimp on the jeans and t-shirt if you have a really beautiful leather jacket. 
Some of the best makers here include Good Wear Leather, Bill Kelso, The Real McCoys, Eastman, and Aero. These brands specialize in making reproductions of vintage flight jackets, and they make them as tough as the originals. Temple of Jawnz is also a favorite among style enthusiasts. They’re sadly closing up shop in a month, but are doing one last call for custom orders. 
The price points for any of these is pretty expensive. We’re talking $750 to $1,500 for a jacket, and some even have waiting lists that stretch back a year. As usual, a more affordable option would be trawling eBay and vintage stores, but what you save in money, you’ll spend in time. You could also go for a similarly rugged jacket style, but one not made from leather. One of my favorite stores, Bench & Loom, has some really handsome pieces, and they’re holding a 20% off sale with the code SPRING20. The code is good for both sweaters and outerwear, with some brands being excluded (Mister Freedom, Schott NYC, Buzz Rickson, and The Real McCoys).

The Simplest Casual Look

Although I enjoy wearing tailored clothes on weekdays, I dress pretty casually on weekends. Lately, that’s meant dark blue jeans with a clean white t-shirt and a nice, brown leather jacket. For shoes, I wear either sneakers or boots, and if it’s cold outside, I layer with a heathered grey sweatshirt. I find it’s one of the simplest, easiest looks you can put together, and depending on your lifestyle, very well suited to casual weekend activities with friends.

For jeans, I really like 3sixteen’s SL-100x model. It’s a slim straight-legged cut made from a medium-weight selvedge denim that doesn’t bag as easily as other brands’. I’ve also been admiring their premium 3sixteen+ line, as well as Flat Heads 3009s and Iron Heart 634s. Those are made from unsanforized denim, which Kiya at Self Edge tells us will yield more interesting fades over time (without the need to forgo washing, thankfully). For something more affordable, check out Albam, Gustin, and Uniqlo’s Made in Japan offerings.

For the t-shirt, I stick to a pretty basic Hanes’ Beefy-T (I get the one with a chest pocket). It has a stoutness that I think works well with this kind of look, and it can be easily found on sale for about $6. Jesse has also recommended Costco’s Kirkland t-shirts for this sort of thing. For something thinner and stretchier, check out Alternative Apparel, which Jesse does bulk orders on every summer, and American Apparel. Levis also has a nice model that’s in between the toughness of Hanes and the fineness of the last two brands.

Finally, there’s the leather jacket. These can get astoundingly expensive, but it’s worth buying the best you can afford. Just as you can get away with a pair of cheap chinos and dress shirt if you have a really nice fitting sport coat, you can skimp on the jeans and t-shirt if you have a really beautiful leather jacket. 

Some of the best makers here include Good Wear Leather, Bill Kelso, The Real McCoys, Eastman, and Aero. These brands specialize in making reproductions of vintage flight jackets, and they make them as tough as the originals. Temple of Jawnz is also a favorite among style enthusiasts. They’re sadly closing up shop in a month, but are doing one last call for custom orders

The price points for any of these is pretty expensive. We’re talking $750 to $1,500 for a jacket, and some even have waiting lists that stretch back a year. As usual, a more affordable option would be trawling eBay and vintage stores, but what you save in money, you’ll spend in time. You could also go for a similarly rugged jacket style, but one not made from leather. One of my favorite stores, Bench & Loom, has some really handsome pieces, and they’re holding a 20% off sale with the code SPRING20. The code is good for both sweaters and outerwear, with some brands being excluded (Mister Freedom, Schott NYC, Buzz Rickson, and The Real McCoys).