Getting a Good Grey Sweatshirt
Every fall season, I can’t seem to stop myself from buying more sweaters, but the one I keep coming back to, year after year, is my reliable grey sweatshirt. For casual use with chinos and jeans, I can’t think of anything better. It’s low-maintenance, sporty, and if the fit is right, can look pretty great.
My favorite sweatshirts are made by Japanese companies such as Buzz Rickson, The Real McCoys, and Strike Gold. These brands specialize in mid-century reproductions, and often use older production techniques (these techniques don’t lend any special advantage, they’re just neat if you care about such things). They’re also thicker and denser than most other sweatshirts on the market. You can find them at them at Self Edge, Blue in Green, Superdenim, and Bench & Loom.
Other really great companies include Archival Clothing, WTAPs, Levis Vintage Clothing, Sunspel, Reigning Champ, Battenwear, Loopwheeler, RRL, and Velva Sheen. Many of these will have their own unique selling points. Archival Clothing, for example, has theirs made in Portland, Oregon by the old-school American manufacturer Columbiaknit, while Levis Vintage Clothing often draws from Levis’ extensive in-house archive. These models tend to be quite expensive, however, so if you want something more affordable, check out Champion, American Giant, Land’s End, Uniqlo, and J. Crew. The last three hold sales pretty often, so you can knock the price down further if you exercise some patience.
Naturally, many people may be wondering what’s the difference between a ~$150 sweatshirt and something that you can find for ~$50. Some of this will be in the detailing, such as some having loopwheeled constructions (which again, are just old ways of making these garments). Some of this will be in the quality of the materials. My Buzz Rickson sweatshirt, for example, is nice and dense, and doesn’t stretch out as easily as the one I bought from J. Crew. It also has a “vintage” fit that I like, which is slightly boxy and short. I think it goes well with the kind of boots, jeans, and jackets I like to wear. 
In the end, however, you just need to find something that fits you well, and works for your budget. Not all sweatshirts have to be dumpy, and not all nice ones have to cost an arm and a leg. If you find that your sweatshirt stretches out easily, just throw it in the wash and put it in the dryer after each wear. It should shrink back to shape. The color might dull from being in the dryer so much, but … it’s a sweatshirt. These look better beat up. 

Getting a Good Grey Sweatshirt

Every fall season, I can’t seem to stop myself from buying more sweaters, but the one I keep coming back to, year after year, is my reliable grey sweatshirt. For casual use with chinos and jeans, I can’t think of anything better. It’s low-maintenance, sporty, and if the fit is right, can look pretty great.

My favorite sweatshirts are made by Japanese companies such as Buzz Rickson, The Real McCoys, and Strike Gold. These brands specialize in mid-century reproductions, and often use older production techniques (these techniques don’t lend any special advantage, they’re just neat if you care about such things). They’re also thicker and denser than most other sweatshirts on the market. You can find them at them at Self Edge, Blue in Green, Superdenim, and Bench & Loom.

Other really great companies include Archival Clothing, WTAPs, Levis Vintage Clothing, Sunspel, Reigning Champ, Battenwear, Loopwheeler, RRL, and Velva Sheen. Many of these will have their own unique selling points. Archival Clothing, for example, has theirs made in Portland, Oregon by the old-school American manufacturer Columbiaknit, while Levis Vintage Clothing often draws from Levis’ extensive in-house archive. These models tend to be quite expensive, however, so if you want something more affordable, check out Champion, American Giant, Land’s EndUniqlo, and J. Crew. The last three hold sales pretty often, so you can knock the price down further if you exercise some patience.

Naturally, many people may be wondering what’s the difference between a ~$150 sweatshirt and something that you can find for ~$50. Some of this will be in the detailing, such as some having loopwheeled constructions (which again, are just old ways of making these garments). Some of this will be in the quality of the materials. My Buzz Rickson sweatshirt, for example, is nice and dense, and doesn’t stretch out as easily as the one I bought from J. Crew. It also has a “vintage” fit that I like, which is slightly boxy and short. I think it goes well with the kind of boots, jeans, and jackets I like to wear. 

In the end, however, you just need to find something that fits you well, and works for your budget. Not all sweatshirts have to be dumpy, and not all nice ones have to cost an arm and a leg. If you find that your sweatshirt stretches out easily, just throw it in the wash and put it in the dryer after each wear. It should shrink back to shape. The color might dull from being in the dryer so much, but … it’s a sweatshirt. These look better beat up. 

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.