I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style.

I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style.

      For as long as I can remember, I've been drawn to skirts and dresses. So much so that when I made my debut on The Who What Wear Podcast in September 2025, I revealed something that surprised my colleagues: I didn’t own a single pair of jeans. While many of our editors have built extensive denim collections over the years, they found it hard to believe that was true. Fast forward nine months to June 2026, and I have news: I finally purchased my first pair of adult jeans.

      I clarify "adult jeans" because it's not that I never wore jeans as a child. One of my key shopping memories is going to Abercrombie in elementary school to grab new pairs for the upcoming school year. However, after a certain point, as I developed hips, finding jeans that fit well became more difficult—and they simply didn’t feel like me anymore.

      As someone who prefers online shopping, ordering jeans has always been a bit of a gamble, and trying them on in-store is a significant hassle. Each brand has its own fit, sizing fluctuates from style to style, and occasionally, there's that dreaded waist gap. Every time I entered a fitting room with a stack of jeans, I became overwhelmed and left without purchasing anything. After numerous shopping trips filled with sold-out sizes, unavailable washes, chaotic SoHo stores, and the incessant struggle of pulling jeans on and off, I decided to give up.

      Overall, skirts and dresses just seem more straightforward. I know my size, which tends to be consistent across brands, and I appreciate that they are less constrictive and allow for more movement. Styling them feels more intuitive, and I always feel more put-together when I wear them, which eliminates the stress of getting dressed.

      That being said, while I believe there's nothing wrong with sticking to what you love, as an editor, it felt like a challenge I wanted to tackle. I was determined to solve it and document my experience. So I resolved to revisit the enduring favorite among editors, numerous celebrities—from Hailey Bieber to Kendall Jenner—and fashion enthusiasts: Levi's.

      In choosing between the 501, 501 Curve, and 501 '90s, I ultimately went with the latter. What convinced me was the description on the website: “Imagine taking everything you adore about the iconic 501 Original and giving it a nineties twist. Boom: you have the 501 '90s. Think of these as a slightly roomier version of our original fit. The easy silhouette has a looser fit, and the rise is a bit lower. The leg design is fully '90s with a relaxed, laid-back fit from hip to hem, taking inspiration from the slouchy (and perfect) 501 jeans our favorite stars wore back then.”

      During my research, I stumbled upon a handy tip from a TikTok video by Reilly Krug. “My life hack for Levi's is to size up three sizes from your usual,” she suggested. “I find that sizing up provides that lower, vintage feel, and they just seem more lived-in, in my opinion.” Since I was committed to online shopping, I decided to order the style in two sizes to ensure I got the fit just right.

      For color options, I would recommend Shout Out Stone or In Love With You, Deep Rinse for dark washes, and Fun Flare or Ever Afternoon for lighter shades.

      Maybe one day I’ll have the patience to become a vintage jeans expert myself, but for now, as a novice in denim, the Levi's 501 '90s have proven to be the easiest solution. As for what I’m eager to try next: Agolde's '90s Straight Jeans, Khaite's Danielle High-Rise Slim-Leg Jeans, Still Here's Childhood Jeans, and Gap's Low Rise '90s Loose Jeans.

      Levi’s 501 '90s Lightweight

      Shop More Editor-Favorite Jeans

      AGOLDE '90s Pinch Waist High-Rise Straight Jeans

      KHAITE Danielle High-Rise Slim-Leg Jeans

      Still Here New York Childhood Jean

      Gap Low Rise '90s Loose Jeans

      Citizens of Humanity Zurie Straight Leg Jeans

I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style. I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style.

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I Didn’t Have a Single Pair of Jeans (I Know), But My Stylish Coworkers Encouraged Me to Try This One Style.

Discover the Levi's favored by Hailey Bieber and Kendall Jenner.