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. 

Since American Apparel has such creepy hiring practices and a total lack of clothing for big women (despite a now-shuttered men-only big & tall line), the very pretty (size 12) Nancy Upton has taken matters into her own hands. She’s entered AA’s “XL Model Search” with a series of amazing satirical photos which she’s blogging here. This lady is awesome. Vote for her.