My Favorite Pairs of Jeans Are Made for Teens

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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 ourJeans Month hub.
Growing up, I almost never wore jeans thanks to a mandated school uniform of polo shirts and trousers in drab gray, navy, and khaki. So post-graduation, with the freedom to determine my own style, jeans didn’t cross my mind; instead I went full peacock, luxuriating in ruffled patterned blouses, pussy-bow sweaters, and drapey velvet skirts. It was only after I moved to New York and found myself on a hike upstate, scrambling down a rocky slope in a silk slip, that I begrudgingly conceded that it made sense to add a low-key jean or two into my rotation.
But where to start? Jeans shopping, as most everyone knows, is a daunting task, especially if you’re petite — I’m five-foot-three. Skinny jeans were a flat-out no; they remind me of middle school, and I don’t feel like the cut suits me. Jeans with even a tiny percentage ofstretchwere also off-limits; I never buy any clothes that contain synthetic fabric, even if it’s a blend. I also purchase the vast majority of my clothes secondhand, which added another layer of complication.
I had a general idea of what I wanted: a mid-rise, straight-leg fit in washed black, and after sifting through hundreds of options fromAbercrombieto Agolde, Calvin Klein to vintage Levi’s, I landed on a pair from Wrangler via Depop. I always approach online thrifting armed with both my body measurements and the measurements of clothing that fits me well, and the Wranglers (when laid flat) corresponded exactly with the sort of fit I was looking for: 13-inch waist, 18-inch hips, 26.5-inch inseam. They were tagged with size Boys 14 Regular, but I decided to take the chance.
When they arrived and I tried them on, the fit was perfect. They had a quintessential “boyfriend” silhouette, because, well, they’re literally meant for boys: loose, relaxed, slightly baggy, with a just-right mid-rise that hit an inch or two below my navel. Like many pairs of kids’ pants, they have elastic bands inside the waistband, which I’ve found very useful, as a lot of pants that fit me in the hips will gap in the waist — I’ll tighten the elastics if I want them to sit higher or loosen them if I’m going for a more low-slung look. And the best part, there was no need for cuffing or tailoring: The hem fell right at my ankle bone.

About six months later, I stumbled across my second pair of boys’ jeans by total accident — I was idly browsing Other People’s Clothes on a Sunday afternoon and a pair of dark blue Levi’s carpenter jeans caught my eye. When I checked the tag, they were labeled Boys 14 Regular; I brought them into the fitting room along with another pair of jeans in women’s sizing, and while the latter was too long with a too-high rise, the carpenter jeans fit like magic, with a straight leg that hit at my ankle and a rise that fell right below my belly button.
I’ve worn both pairs on subsequent hiking trips, on nights out dancing, and even on six-hour plane rides and found them to be highly comfortable and easy to move around in. Because they’re made for kids andteensprone to running around and roughhousing, the fabric and stitching are fairly durable, able to withstand frequent washings and a fair amount of wear and tear. I have a monthly dry-cleaning budget for my clothes that need babying, so it’s a welcome relief to be able to toss these into the washer and dryer without sparing a second thought.

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I found the exact models of my two pairs on eBay without much effort — try search terms like “loose fit,” “100% cotton,” and “adjustable waist.”
Since both were sourced secondhand, however, I had little sense of the current landscape of boys’ jeans, so I ventured out to do some reconnaissance. My first stop was the Herald Square Macy’s, where I figured I could maximize efficiency by trying on jeans from multiple brands all at once. After some poking around in the boys’ department, I noticed that most brands carry up to a size 18, and even up to size 20 at Levi’s, which may potentially fit non-petites. However, I regret to report that my preferred straight and relaxed cuts were far outnumbered by skinny and tapered fits. I pulled all the non-skinny pairs I could find and ended up with four from Levi’s, Guess, Tommy Hilfiger, and Epic Threads (Macy’s in-house line).
Of the four, the Epic Threads pair ended up being my favorite, probably because it was the most relaxed fit of the bunch. (Even the “straight” legs seemed to err on the slimmer side.) Lengthwise they were all perfect and fit me well in the hips and trunk; all except the Guess pair offered an adjustable elastic waist. My biggest gripe was that none of the jeans were 100 percent cotton, which I assumed would be easy enough to find; instead, the Guess and Epic Threads pairs contained 1 and 2 percent of elastane, respectively, and the Levi’s and Tommy Hilfiger pairs were a cotton-polyester blend. The price points, though, couldn’t be beat: While a pair of adult jeans at Levi’s can run close to $100, the boys’ jeans generally hover between $20 and $50.

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When I left Macy’s, I stopped by Old Navy across the street. There, I found a wider range of cuts: baggy, straight, taper, slim, and skinny. I tried on the baggy, straight, and slim, and all three were boxier, overall, than the jeans I tried on at Macy’s — they fit well in the hips but gapped noticeably in the waist, and I had to pull in the adjustable waistbands a good inch or two on either side. I liked the baggy pair the most and was pleased to realize it was the only pair I encountered that was made of 100 percent cotton (the other two contained 2 percent elastane). However, I prefer a dark wash over light and medium washes, so I returned them to the rack.
And while I didn’t find my perfect third pair during this mission, I suspect it’s only a matter of time for the boys’ denim pendulum to swing back around to looser and more relaxed fits. But if you’re petite and don’t mind a slimmer leg and a touch of stretch in your jeans, now is the moment to give the boys’ section a gander.

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