Los Angeles–based Lenny is redefining how vintage denim can serve as the cornerstone of a bespoke luxury experience.
“I wanted to find a way to create a sustainable company that also focuses on custom fit,” founder Lindsey Davidson-Paley told SJ Denim.
“I’ve always loved vintage denim—the silhouettes, the materials. The quality is always better than modern day denim, not to say I don’t love modern day denim as well, but what I really love is the aspect of sustainability and not having to create something entirely new.”
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Out of this love for vintage denim, Davidson-Paley founded Lenny in 2021—a peak time for secondhand denim as the pandemic flashed a spotlight on the fashion industry’s negative impact on the environment.
However, she also set out to solve a universal problem: finding jeans that fit. Jeans—be it vintage or new—are rarely ever a perfect fit, she said.
“The two of the biggest challenges that we see here are women who either have like a smaller waist and a bigger butt, or the opposite, where they’re almost kind of square shaped so their waist is larger, and their butt is smaller. They struggle with jeans that fill out their butt,” she said.
Vintage jeans are especially challenging due to the limited range of sizes available.
“It’s much easier to find larger sizes. I think people have this misconception that they can’t wear vintage jeans if they’re a larger size, but it’s the complete opposite. I would say our bread and butter, in terms of inventory is like, anywhere from a vintage 32 to 40,” she said.
Davidson-Paley emphasized how the goal is to fine-tune the fit of an existing silhouette. “We really try to stay as true to the vintage denim as possible. We stay away from taking the legs of the jeans in because the whole point of buying vintage denim is getting the vintage look,” she said. “When you start recreating the silhouette, you might as well just start from scratch and buy a modern-day jean.”
Lenny works with customers to find exactly what they want and how to make it work for their body. For example, for a customer that wants a straight leg, the Lenny team would recommend a Levi’s 501 or 505. Though Davidson-Paley noted that Wrangler “makes great straight legs too.”
Lenny does not work with any denim brands, nor does it tailor jeans that customers bring in. The company works with several suppliers to source vintage jeans, from which customers can choose from, and then have fitted to their body either at Lenny’s L.A. studio or at one of the various pop-ups it holds across the U.S. Virtual fittings are also available.
The selection is mostly ’90s vintage jeans by Levi’s, Wrangler and Lee, though Davidson-Paley said there are some great deadstock dark jeans from the ’70s. Denim from the ’80s and early 2000s are also sprinkled into the mix. “It’s cyclical like the rest of fashion,” she noted.
Customized jeans retail for $445 and include all alternations and shipping. Jeans ordered from the L.A. studio take 4-6 weeks to complete. Custom Lenny jeans from a pop-up takes 8-10 weeks.
Pop-ups have become a key strategy for Lenny to meet the growing demand for perfectly fitted vintage jeans. Davidson-Paley said the brand plans to host 10 pop-ups across various markets in 2026.
“For us, because we’re L.A. based and we have such a demand, we really try and see as many people as possible in different cities,” she explained, noting that New York, Dallas, Atlanta, and Chicago have been among the most successful stops.
To maximize the number of clients they can see in a short period, the Lenny team typically books two clients at a time for 30-minute fittings during pop-ups. In contrast, customers visiting the Los Angeles studio can enjoy 45-minute one-on-one appointments. “Though the pace is quicker at pop-ups compared to L.A. Davidson-Paley said the results are just as precise.
Social media and word-of-mouth have been key in sharing Lenny’s story with a wide and diverse audience.
“There is no typical Lenny client. We work with both men and women, even though we generally have marketed more towards women. We’ve had young 20s, and we’ve had a few clients in their 80s. We really see such a wide range of clients,” Davidson-Paley.
Just like a great pair of jeans, she adds, “No one fits into a particular mold.”
