Nothing defines the American fashion experience more than trying to find the perfect pair of blue jeans. They're the foundation of any wardrobe outside of tailored clothing, the casual equivalent of gray flannel trousers. This old Australian documentary on Levi's summed it up best:
The symbols that tell a story in a twinkling of an eye are usually everyday products, but some are very special. The Eiffel Tower says France, but the little Sony walkman says Japan. The archetypal symbols that yell America are the Coke bottle and Levi's Strauss jeans. They all enjoy the prestige of being regarded as design classics. [...] Film stars, American presidents, student protestors, and rock musicians have all worn the 501. From gold mining through protest, to what they are today, [blue jeans] are the story of the acceptable uniform for non-conformity.
Some men look great wearing tailored clothing year-round, but I can't imagine building a wardrobe without blue jeans. They're practical, hard wearing, and frankly look great. Even Bruce Boyer, the closest thing we have today to an arbiter elegantiarum in classic menswear, occasionally wears a pair. Over the years, I've cycled through at least a dozen models trying to find the Platonic ideal. The truth is the perfect pair of jeans doesn't exist - a lot depends on what other clothes you like to wear. Here are ten models, however, that I think are notable.
3sixteen is about as close as I've come to finding the perfect pair of jeans. Or, at least, they're the ones I'd wear if I had to stick to one brand. I prefer their straight-legged fit - what the company calls their SL model - which comes in a range of fabrics. There's the lighter weight 12oz selvedge denim and a rugged five-pocket chino. If you're looking to get your first pair, I'd go with their standard SL-100x jeans, which is a mid-weight, 14.5oz sanforized denim specially woven for them by Kuroki Mills in Japan.
The best part is the fit. These are genuinely slim without being skinny, with a mid-low rise and slight taper that make them work across a range of casualwear styles. The denim also just fades beautifully. Mine look like this.
You can find 3sixteen at Self Edge, Standard & Strange, and the company's own online shop. They're also on sale right now at The Class Room at 20% off if you use the checkout code THANKYOUHOUSTON.
I love my 3sixteens, but they don't work with everything. Notably, the SL cut is a little too low for wearing with sport coats (they have two classic cuts, although I haven't tried them). For things such as tucked-in button-downs and casual tailoring, I prefer Drake's jeans, which Blackhorse Lane makes for them in London. The cut is a little fuller; the rise a touch higher. There's again a slight taper below the knees to give the jeans some shape, but it's still a reasonably conservative cut.
Levi's Vintage Clothing 1947 501s ($270)
I also just love the details - single needle stitching, felled seams, and a one-piece fly that opens flat. Even without a tailored jacket, these look great with things such as Shetland sweaters and waxed cotton field jackets. Basically the sorts of things sold at Drake's. You can find their jeans at their online shop, as well as their NYC store.
Another great, conservative cut that works just as well with classic casualwear as it does with sport coats. Levi's flagship 501 jeans have changed a lot over the years, and this reissue from their 1947 model features a slim-straight leg and slightly higher rise. It's made from Cone Mill's White Oak denim, which has a slightly smoother and more consistent character than some of the niche Japanese fabrics denim-heads drool over. A little boring if you're looking for distinctive fades, but perfect if you want a classic look.
If you like this model, but want a slightly more tapered fit, try Levi's Vintage Clothing's 1954 501s. Either would do well in the company's New Rinse finish, which helps takeout some of the guesswork in shrinkage. Good for guys who may be new to high-end denim.
Our Legacy First Cut ($199) 
You can find Levi's Vintage Clothing jeans at End, Unionmade, and Mr. Porter. The 1954 model is also on heavy discount right now at Club Monaco (use the code FALL30 to knock an additional 30% off the sale price).
Most of the jeans on this list are great for anything that could be vaguely considered classic. Sometimes, however, you want a pair of slim-tapered jeans that go with more contemporary casualwear styles. I like Our Legacy's First Cut as a sort of do-all. They're certainly very slim, but the slightly roomier top block gives them the illusion of shape without cutting off circulation in your ankles.
Orslow Ivy League Slim 107 ($250) 
These aren't selvedge, however, if that matters to you. On the upside, they're available in various washes, which is nice if you're looking for a lighter color. My only gripe is the buttons, which are a bit thicker than what you'll find elsewhere. Not a deal-breaker, but something I wish was changed.
Neighbour, East Dane, and End all carry Our Legacy's First Cut. Notre also has the light-washed pair you see above on sale right now in a size 33.
Another great do-all. Orslow's 107 model is a little slimmer than Our Legacy's First Cut, but it still works reasonably well across a range of contemporary styles. I like how Gerry in Melbourne wears them with almost everything - from trim topcoats to shawl collar cardigans to Japanese workwear. George at BRIO also uses Orslow's slightly fuller, slim-straight 105 cut for dressing down sport coats.
The best part of these is the rise. Jeans this slim are usually meant to be worn low on the hips, which only really works for 20 year-olds and waif thin models. Orslow's 105 and 107 cuts, on the other hand, come up a bit higher on the body, while still giving you that very slim leg-line. If you've ever felt the slim-straight models mentioned above look a bit shapeless, Orslow's 107 are for you.
Stevenson Overall Co. 767 ($200)
You can find Orslows almost everywhere - Mr. Porter, Need Supply, End, Superdenim, and Standard & Strange. They come in one, two, and three year washes, which give you an increasingly broken-in look without having to do any of the work. Good for guys who don't wear jeans often.
C.O.F. Studio, otherwise known as Circle of Friends, prides itself on making jeans from straight to finish using the company's social network. C.O.F. founder Per Fredriksson is personally friends with every factory involved in the process. The denim is woven by Candiani, buttons from Cobrax, leather from Panama Trimmings, cutting and sewing by Feder, and washing by Lavaredo. The entire manufacturing process is also done in Italy.
The company has a nice story, but I mostly like them because they make skinny jeans a middle-aged guy like me can actually wear. Most skinny jeans fit way too tight and sit much too low - making them both figuratively and literally hard to pull off. Circle of Friend's M1 and M2 are skinny without fitting like Saint Laurent. And for things such as black leather jackets, you'll want something like this instead of a fuller straight-leg.
The Flat Head 3009 ($315) 
I buy my C.O.F. Studio jeans at Standard & Strange.
Stevenson's jeans were inspired by designs made in the 1920s, before the invention of bartacking machines, so all the belt loops have been secured by running a single-needle machine back and forth. In fact, the entire garment is single-needle made - even the two lines you see running around the curved pockets are just two single-needle stitches running parallel to each other (an incredible level of detail at this price point). The back pockets, coin pocket, and belt loops also feature a subtle scalloped design. The jeans have a classic workwear feel without being overly repro.
I originally bought the company's 767 Santa Rosa model because I wanted a slightly fuller slim-fit that would work well with hefty boots. The jeans have shrunk a little since then - a testament to denim's inherent instability that I think makes bespoke jeans pointless. That said, they still get a considerable amount of wear with things such as service boots and heavy flight jackets.
Self Edge carries Stevenson Overall Co., although they don't have the 767 model. You'll have to source those direct from Stevenson themselves.
APC New Standard ($195)
Similar to Stevenson's 767s, these are a slightly fuller straight-leg that would work well for athletic builds. Or like me, guys who want something to fit over heavier looking boots. The company's denim is famous for its slightly crunchier and hairier texture, which give them a more distinctive wear pattern over time. After about a year of consistent wear, you'll get really nice, almost electric blue fades, which you can see at Heddels.
I admit, I don't wear mine that often. The fuller fit works well with certain kinds of workwear, but less so for the sort of contemporary casualwear and slightly off-beat takes on workwear I find myself in these days. That said, if you want something to go with Chuck Taylors and a heavy flannel shirt, it would be hard to find something better (see how Andrew at 3sixteen dresses for inspiration). A solid jean for guys who want to look well-dressed without seeming fussy. You can find The Flat Head's jeans at Self Edge.
It's almost impossible to characterize Chimala's jeans because the fits and finishes can change from season-to-season. That said, they have some great anti-fit models that are meant to be worn full, high, and slightly cropped (such as what you see above). They go great with slightly off-beat takes on workwear. You just have to be willing to be a bit more adventurous with how clothes are supposed to fit.
Chimala is also really good at tasteful, slightly pre-distressed details, which look a lot better in-person than they do online. The brand basically makes the sorts of things you'd imagine coming out of the best vintage workwear archive, but doesn't require you to do any of the digging (outside of emptying out your pockets, anyway). I bought their chambray a few years ago and it's one of my favorite causal shirts.
Chimala has limited distribution in the US, but you can find them at Unionmade, Mr. Porter, and J. Crew.
If you were into raw, selvedge denim ten years ago, these were basically everyone's go-to. The raw denim, slim fit, and lack of branding made these stand out during the early-aughts, but they've lost some of their glow over the years. It's not terribly hard to find better alternatives to APCs nowadays, especially if you're looking for something more unique or affordable ( Gustin, Unbranded, and Uniqlo are all good starting places if $150+ seems like an outrageous amount to pay for jeans).
APCs will always have a special place in my heart because they were my first pair of premium denim. That said, I find the fit and quality a bit disappointing now. I'll never know how I fit into those super low-rise cuts. Or why I put up with how much the denim stretches over time. A decade ago, it seemed reasonable to wade through hundreds of online forum pages to figure out your size. And soaking your jeans every once in a while to shrink them back into shape. I just can't be bothered anymore.
That said, they were popular once for a reason, and today you can find them almost anywhere. I'd start at Mr. Porter just for the free shipping and returns. Sizing can still be a headache. Don't me to ask how much you should size down; there's a billion-page StyleForum thread for that.
