For as long as I can remember, I've gravitated toward skirts and dresses. So much so that when I first appeared on The Who What Wear Podcast in September 2025, I shared something that shocked my colleagues: I didn't own a single pair of jeans. While most of our editors have extensive denim collections they've spent years curating, they couldn’t quite understand how that was possible. Nine months later, June 2026, I have news: I finally bought my first pair of adult jeans.
I specify "adult jeans" because it's not as though I never wore jeans as a child. One of my most formative shopping memories is actually going to Abercrombie in elementary school to stock up on new pairs for the school year. But sometime after that, I got hips, and finding jeans that fit perfectly became more complicated—and they just didn’t feel like me anymore.
As someone who prefers shopping online, ordering jeans has always been hit or miss for me, and trying them on in person is a whole ordeal. Every brand fits different, sizing varies from style to style, and sometimes there's even the dreaded waist gap. Each time I'd go into a fitting room with a pile of jeans, I'd get overstimulated and leave empty-handed. After multiple shopping trips filled with sold-out sizes, unavailable washes, overcrowded SoHo stores, and the hassle of pulling jeans on and off over and over, I gave up.
Overall, skirts and dresses just feel easier. I know my size, and it’s fairly consistent across brands, and I love that they’re less restrictive and allow for more movement. Styling them also comes more naturally to me, and I always feel the most put-together in them, which takes the guesswork out of getting dressed.
That all said, even though I think it's perfectly fine to stick with what you love, as an editor, it still felt like a shopping challenge I wanted to solve. I became determined to figure it out and write about it. So I decided to revisit the tried-and-true favorite of editors, countless celebrities—from Hailey Bieber to Kendall Jenner—and fashion people everywhere: Levi's.
Levi's 501 '90s
Torn between the 501, 501 Curve, and 501 '90s, I ended up choosing the latter. What won me over was the description on the website: “Imagine if you took everything you love about the legendary 501 Original and gave it a nineties refresh. Boom: you have the 501 '90s. Think of these as a slightly wider version of our original fit. The easy silhouette sits a little looser, the rise a little lower. Then there's the leg. We went full-on '90s and gave them a relaxed, laid-back fit from hip to hem, inspired by those slouchy (and flawless) 501 jeans our favorite celebrities wore in that era.”
During my research, I came across a tip from a TikTok video by Reilly Krug. “My life hack for Levi's in particular is sizing up three sizes from your usual,” she shares. “I find that by sizing up, you also get that lower, vintage-esque feel, and they just feel more lived-in, in my opinion.” Since I was committed to online shopping, I ended up ordering the style in two sizes to make sure I got the fit right.
For shades, I'd recommend Shout Out Stone or In Love With You, Deep Rinse for a dark wash, and Fun Flare or Ever Afternoon for lighter washes.
Maybe someday I'll have the patience to become a vintage-jeans connoisseur myself, but for now, as an impatient denim novice, the Levi's 501 '90s have been the simplest solution. As for what I'm curious 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.
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