Welcome to Jeans Month on the Strategist, where we’re obsessively vetting denim — from trying on every pair at the Gap to asking dozens of stylish people about their favorite fits. For more, head to our Jeans Month hub.
Like many young men who came of age toward the end of the great recession, I believed in the value of raw denim. A single pair of jeans may have cost the lion’s share of my bimonthly take-home pay, but think of the cost per wear amortized over a decade. “Buy it for life” was a seductive proposition for those halcyon days, and indeed, the handful of pairs I’d crowdfunded on Kickstarter from my first paychecks out of college stayed in regular rotation throughout the rest of my 20s. Far too long for pants that, in retrospect, never fit right.
After many years of trying, I can confidently say that if a pair of pants isn’t comfortable after doing a few squats, no amount of tub-soaking, drying on-body, not-washing, or washing with intention will ever fix them. When I finally admitted that my enjoyment of a pair of pants had more to do with how they fit my body than the heritage source of its materials, a friend recommended I try a pair of A.P.C.’s Martin jeans.
In contrast to the slimmer cuts that made the brand a vanguard of the late-aughts raw-denim boom, these have a high-rise, straight-legged fit inspired by ’90s vintage denim. And they are perfect. The material is substantial yet soft, and the cut is just fitted enough to be flattering yet roomy enough not to constrict my calves and glutes while sitting. I would have bought several pairs in every color and wash if they didn’t start at $295. Rather than sign up for Klarna to fund a wardrobe refresh, I decided to go straight to the source of inspiration by hunting for actual vintage denim from the ’90s as a more affordable alternative.
As luck would have it, the very first pair of made-in-the-USA Levi’s I ever ordered off of eBay were exactly what I was looking for. These red-label 550s fit comfortably around my waist without a belt; had just enough room through the hips and thigh to flatter my butt while standing without constricting it while seated; and tapered subtly to the hem, resting gently across the top of my foot and draping ever so slightly over my ankle bones to form the type of semicircular break that even custom tailoring struggles to achieve. Best of all, they only cost me $34.45, including shipping.
Being new to this game, I thought I now had “my size” and that acquiring more pairs would be a simple matter of judging the wear and finish of each triggered alert. Alas, my initial success turned out to be beginner’s luck. Despite all sharing the same make, model, and nominal size, no two pairs I purchased ever fit the same. Going off of measured sizes was no guarantee either. How can one pair of pants that puckers tightly across the hips read the same on a ruler as another that feels loose and looks frumpy? I could only conclude that 30 years of washing and drying takes an inevitable and randomized toll on any garment. If I wanted to find jeans that fit reliably, I’d have to find ones still in production.
Modern Levi’s 550s were an obvious starting point, but they simply don’t make them like they used to. They are wide without being wide-legged, and the softer material drapes formlessly down the hips in a chaste and boxy silhouette. On the other hand, modern 501s were tight in all the wrong places. They’d squeeze my thighs like a blood-pressure monitor cuff whenever I sat down.
And while I like how Carhartt’s boxy canvas carpenter pants fit for what they are, I don’t like how it translates to blue jeans. They are not wide enough to read as wide, nor fitted enough to flatter; they just feel a bit homely.
I had already given up hope when the answer found me while jogging through Fort Greene. Hanging off of a wrought-iron fence on a tree-lined block of brownstones just steps from the park was an Ikea bag full of free clothing, among which was a pair of stonewashed Dickies jeans in 30x32, my exact size. I’d never strongly considered these as an option because I didn’t like the lower rise on other Dickies pants I’d tried. But the price was right, so I rolled them up and tucked them under my arm for the rest of the run home.
I tried them on upon arriving at my apartment and was shocked by how much I liked them. They felt similar to the Martins from the waist through the thigh, but with just a pinch of extra space — enough to fit over a pair of long johns on a cold day. That extra room continues to the cuff, resulting in a relaxed cut that’s comfortable and unrestrictive in every position. The stonewash lends a pleasant softness to the otherwise sturdy material that helps it drape naturally along the body. Perhaps rarest of all among today’s new denim options, they sit high enough on the waist to not require a belt if you buy the correct size. Dickies aptly calls this its “regular fit,” and as indicated by the breadth of its sizing options and choice of models, the brand means that inclusively.
Despite costing $30, they have the brass hardware, YKK zipper, contrast stitching, and five-pocket design shared by most blue jeans at any price. I bought a new pair the other weekend and was initially concerned by how tightly they squeezed my thighs straight out of the bag. But a few quick squats were all that was needed to get them to fit like the old pair.
The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.
