Five Great Things That Come With A Leather Jacket
I wear sport coats most days of the week, but for the last two years or so, I’ve been breaking it up a bit with leather jackets. In that time, I’ve found leather jackets to have some nice advantages over tailored clothing. 
Shirts
Paul Newman looks great above in his button-up shirt, but for me, a leather jacket really calls for a t-shirt. The good news is that t-shirts can be had for not too much money. Jesse sells Alternative Apparel ones every summer at a wholesale price. They’re soft, finely knitted, and somewhat stretchy. I wear Hanes Beefy Tees myself, which are more stout. I’ve also heard good things about Uniqlo’s t-shirts, although I’ve never tried them.
All of these can be had for less than ten bucks a piece, which means you can get a whole week’s worth for less than the price of a good dress shirt.
Pants
Similarly, jeans can be had for much less than wool trousers. Unbranded and our advertiser Gustin get regularly recommended in the denim community, and they sell raw, selvedge denim options for about $85 a pair. APC New Standards retail for $185, but can sometimes be found on sale. 
The upside to jeans isn’t just their price, however. It’s the material. Denim is an exceptionally tough fabric and can take a lot of abuse. Some guys wear their jeans every day for two years before retiring them. Do that to a pair of grey flannel trousers and they’ll disintegrate in a few months.
Shoes
Shoes are a bit more tricky. With a heavy horsehide or cowhide jacket, you might need something like a chunky boot. With a lighter lambskin or goatskin jacket, however, you can wear canvas sneakers. I often wear this jacket, for example, with white Chuck Taylor high tops, which I bought for $50. There’s no good dress shoe that retails for $50.
Fit
There are few things that can smarten you up more than a sport coat or suit, but they are admittedly difficult to fit. This might be because of their construction: the shoulder pads, wadding, canvassing, haircloth, etc. Add to that the stylistic details (width of the lapel, shape of the quarters, pitch of the arm, height of the gorge, etc.), and you can see how complicated a tailored jacket can get.
On the other hand, leather jackets (and everything that goes with them) have a lot more wiggle room. It’s OK if your jacket doesn’t look like it was perfectly tailored and if your jeans aren’t hemmed to a perfect shivering break. In fact, they shouldn’t look like that anyway. 
Care
Finally, it’s nice to not have to iron a shirt before you go out, worry about whether a dry cleaner will ruin your jacket, or care if some food drips onto your clothes. Everything above – the t-shirt, jeans, sneakers, and jacket – is meant to be worn and beat up. Some items (such as the jeans and sneakers) look better after they’ve been worn in. Others (such as the t-shirt) are cheap enough to easily replace.
Granted, the leather jacket itself can be pretty expensive. You’re either going to spend a lot of money for a new one, or a lot of time searching for something used. On the upside, once you find one you like, there are five great things that come with it. 

Five Great Things That Come With A Leather Jacket

I wear sport coats most days of the week, but for the last two years or so, I’ve been breaking it up a bit with leather jackets. In that time, I’ve found leather jackets to have some nice advantages over tailored clothing. 

Shirts

Paul Newman looks great above in his button-up shirt, but for me, a leather jacket really calls for a t-shirt. The good news is that t-shirts can be had for not too much money. Jesse sells Alternative Apparel ones every summer at a wholesale price. They’re soft, finely knitted, and somewhat stretchy. I wear Hanes Beefy Tees myself, which are more stout. I’ve also heard good things about Uniqlo’s t-shirts, although I’ve never tried them.

All of these can be had for less than ten bucks a piece, which means you can get a whole week’s worth for less than the price of a good dress shirt.

Pants

Similarly, jeans can be had for much less than wool trousers. Unbranded and our advertiser Gustin get regularly recommended in the denim community, and they sell raw, selvedge denim options for about $85 a pair. APC New Standards retail for $185, but can sometimes be found on sale. 

The upside to jeans isn’t just their price, however. It’s the material. Denim is an exceptionally tough fabric and can take a lot of abuse. Some guys wear their jeans every day for two years before retiring them. Do that to a pair of grey flannel trousers and they’ll disintegrate in a few months.

Shoes

Shoes are a bit more tricky. With a heavy horsehide or cowhide jacket, you might need something like a chunky boot. With a lighter lambskin or goatskin jacket, however, you can wear canvas sneakers. I often wear this jacket, for example, with white Chuck Taylor high tops, which I bought for $50. There’s no good dress shoe that retails for $50.

Fit

There are few things that can smarten you up more than a sport coat or suit, but they are admittedly difficult to fit. This might be because of their construction: the shoulder pads, wadding, canvassing, haircloth, etc. Add to that the stylistic details (width of the lapel, shape of the quarters, pitch of the arm, height of the gorge, etc.), and you can see how complicated a tailored jacket can get.

On the other hand, leather jackets (and everything that goes with them) have a lot more wiggle room. It’s OK if your jacket doesn’t look like it was perfectly tailored and if your jeans aren’t hemmed to a perfect shivering break. In fact, they shouldn’t look like that anyway. 

Care

Finally, it’s nice to not have to iron a shirt before you go out, worry about whether a dry cleaner will ruin your jacket, or care if some food drips onto your clothes. Everything above – the t-shirt, jeans, sneakers, and jacket – is meant to be worn and beat up. Some items (such as the jeans and sneakers) look better after they’ve been worn in. Others (such as the t-shirt) are cheap enough to easily replace.

Granted, the leather jacket itself can be pretty expensive. You’re either going to spend a lot of money for a new one, or a lot of time searching for something used. On the upside, once you find one you like, there are five great things that come with it. 

Hanes Crew Socks
As I’ve gotten older and my style has matured, I’ve found that my choices in socks have become really basic. For dress trousers and chinos, I usually wear solid navy over-the-calf socks made from either cotton or wool blends (cotton if it’s hot; wool otherwise). I really like the ones from Marcoliani and Dapper Classics, but Bresciani is also nice (though, from my experience, some of their patterned socks are a bit more delicate than other brands’). For something more affordable, you can get Pantherellas at 35-40% off using one of Sierra Trading Post’s DealFlyer coupons, or just pick up some basic Gold Toes.
Dress socks are a bit strange to wear with jeans though, so for those times, I wear simple, grey, cotton crew socks. In the past, I’ve bought mine from Uniqlo and Land’s End. I like Uniqlo’s slightly more “retro” designs, but like Jesse, have found Land’s End to hold up a bit better (Uniqlo’s are cheaper, but they tend to fuzz up in the wash).
On a whim earlier this year, I picked up some of these basic grey crew socks from Hanes. They often run 25%-off promotional specials if you buy over a certain amount, which made these socks, coupled with some much needed white Beefy Tees, cheap enough to try.
I’ve been wearing them pretty hard and consistently this past summer, and I’m really impressed with how well they’ve held up. No fuzzing, no loss in elasticity, and they stay up on my leg for the most part throughout the day. Best of all, they cost less than $2 a pair. These are nice affordable basics in the most reasonable definition of affordable. That’s much appreciated given how expensive other “affordable basics” are nowadays.

Hanes Crew Socks

As I’ve gotten older and my style has matured, I’ve found that my choices in socks have become really basic. For dress trousers and chinos, I usually wear solid navy over-the-calf socks made from either cotton or wool blends (cotton if it’s hot; wool otherwise). I really like the ones from Marcoliani and Dapper Classics, but Bresciani is also nice (though, from my experience, some of their patterned socks are a bit more delicate than other brands’). For something more affordable, you can get Pantherellas at 35-40% off using one of Sierra Trading Post’s DealFlyer coupons, or just pick up some basic Gold Toes.

Dress socks are a bit strange to wear with jeans though, so for those times, I wear simple, grey, cotton crew socks. In the past, I’ve bought mine from Uniqlo and Land’s End. I like Uniqlo’s slightly more “retro” designs, but like Jesse, have found Land’s End to hold up a bit better (Uniqlo’s are cheaper, but they tend to fuzz up in the wash).

On a whim earlier this year, I picked up some of these basic grey crew socks from Hanes. They often run 25%-off promotional specials if you buy over a certain amount, which made these socks, coupled with some much needed white Beefy Tees, cheap enough to try.

I’ve been wearing them pretty hard and consistently this past summer, and I’m really impressed with how well they’ve held up. No fuzzing, no loss in elasticity, and they stay up on my leg for the most part throughout the day. Best of all, they cost less than $2 a pair. These are nice affordable basics in the most reasonable definition of affordable. That’s much appreciated given how expensive other “affordable basics” are nowadays.

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).

For $50 You Can Buy …
Following on my “style for college students" post, I thought I’d suggest some "under $50" options that I think would work well for students. Above is what I sometimes wear on weekends if I have errands to run, but I think it can also work for someone in college. 
Shoes: The canvas shoes are a collaboration project by Billy Reid and K Swiss, and they’re on sale right now at J Crew for $30 (use the code OURTREAT). I think they work well with casual chinos and jeans. If you want other options, LL Bean Signature sometimes discounts their blucher and ranger mocs to about $50, and I think they can be worn with the same things. 
Sweatshirt: The grey sweatshirt above is by Onassis. The fit on their website looks skinnier than how mine wears, but perhaps they had the model size down (or maybe they changed the cut). Either way, it’s a decent, casual sweatshirt, albeit thinner than other models on the market. For other affordable options, check out Uniqlo and J Crew (the second of which offers them in grey and navy). J Crew’s cost over $50, but hardly a thing in their store doesn’t make to their end-of-the-season sales.
White tees: I usually wear my sweatshirt over a Levi’s 1950s pocketed tee, but those don’t seem to be online at the moment (they might have them in-store though). A similar model seems to be the pocketless version. If you wait, those go on sale for about $9. Hanes’ beefy tees are also good, cheap beaters. For more options, look into Alternative Apparel (which I know Jesse likes), American Apparel, Uniqlo, J Crew, and Velva Sheen. 
OCBDs: You also can pair the grey sweatshirt with an oxford cloth button-down, which in turn will give your collarline some more structure. The cheapest ones I know of are at Uniqlo, but Brooks Brothers and Land’s End Canvas will often discount theirs to about $35. Here’s some striped ones from Brooks now for about $40.  
Jeans and chinos: My preferred jeans are 3Sixteen’s SL-100x, which I think are one of the best values on the market right now. They’re expensive, but the fit and quality of the denim and construction are excellent. For something cheaper, check out Uniqlo’s Made in Japan line or Gap’s selvage jeans. For something cheaper still, Levis has a bunch of options, so long as you stay clear of any pre-distressed stuff. The non-raw, non-selvedge stuff won’t age as beautifully, but they’re also much more affordable. Alternatively, you can wear the above with Uniqlo’s vintage chinos, which are on sale right now for $40. Jesse has recommended them in the past. 
Belt: Finally, I bought the belt above for $20 at a local jean shop, but you can buy nicer belts from Voyej, Corter, and Don’t Mourn Organize.
The best thing about everything here is that nothing requires much maintenance. I know most college students don’t have time to iron their clothes, polish their shoes, or do any of the other recommendable things for clothing care. The stuff you see above are all items you can throw on, not pay too much attention to, and not worry if things get stained. These are the kind of clothes that look better beat up than brand new anyway. Pretty much ideal if you sleep in libraries, go to parties where cheap beer is often spilled, and don’t even own an iron. 

For $50 You Can Buy …

Following on my “style for college students" post, I thought I’d suggest some "under $50" options that I think would work well for students. Above is what I sometimes wear on weekends if I have errands to run, but I think it can also work for someone in college. 

  • Shoes: The canvas shoes are a collaboration project by Billy Reid and K Swiss, and they’re on sale right now at J Crew for $30 (use the code OURTREAT). I think they work well with casual chinos and jeans. If you want other options, LL Bean Signature sometimes discounts their blucher and ranger mocs to about $50, and I think they can be worn with the same things. 
  • Sweatshirt: The grey sweatshirt above is by Onassis. The fit on their website looks skinnier than how mine wears, but perhaps they had the model size down (or maybe they changed the cut). Either way, it’s a decent, casual sweatshirt, albeit thinner than other models on the market. For other affordable options, check out Uniqlo and J Crew (the second of which offers them in grey and navy). J Crew’s cost over $50, but hardly a thing in their store doesn’t make to their end-of-the-season sales.
  • White tees: I usually wear my sweatshirt over a Levi’s 1950s pocketed tee, but those don’t seem to be online at the moment (they might have them in-store though). A similar model seems to be the pocketless version. If you wait, those go on sale for about $9. Hanes’ beefy tees are also good, cheap beaters. For more options, look into Alternative Apparel (which I know Jesse likes), American Apparel, Uniqlo, J Crew, and Velva Sheen
  • OCBDs: You also can pair the grey sweatshirt with an oxford cloth button-down, which in turn will give your collarline some more structure. The cheapest ones I know of are at Uniqlo, but Brooks Brothers and Land’s End Canvas will often discount theirs to about $35. Here’s some striped ones from Brooks now for about $40.  
  • Jeans and chinos: My preferred jeans are 3Sixteen’s SL-100x, which I think are one of the best values on the market right now. They’re expensive, but the fit and quality of the denim and construction are excellent. For something cheaper, check out Uniqlo’s Made in Japan line or Gap’s selvage jeans. For something cheaper still, Levis has a bunch of options, so long as you stay clear of any pre-distressed stuff. The non-raw, non-selvedge stuff won’t age as beautifully, but they’re also much more affordable. Alternatively, you can wear the above with Uniqlo’s vintage chinos, which are on sale right now for $40. Jesse has recommended them in the past. 
  • Belt: Finally, I bought the belt above for $20 at a local jean shop, but you can buy nicer belts from VoyejCorter, and Don’t Mourn Organize.

The best thing about everything here is that nothing requires much maintenance. I know most college students don’t have time to iron their clothes, polish their shoes, or do any of the other recommendable things for clothing care. The stuff you see above are all items you can throw on, not pay too much attention to, and not worry if things get stained. These are the kind of clothes that look better beat up than brand new anyway. Pretty much ideal if you sleep in libraries, go to parties where cheap beer is often spilled, and don’t even own an iron.