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In the early oughts, luxury denim was defined by the logo stitched on your back pocket: Seven for all Mankind, True Religion — you get the gist, or you lived it.
Today, however, luxury is defined quite differently.
“It” girls, influencers and stylists alike can most often be found in jeans from purveyors of vintage denim, rather than jeans from any singular brand. Some of the retailers have built cult-like followings themselves.
“In the past few years, more people have started to rework Levi’s and resell them. … It’s an amazing business to be in. It’s just skyrocketing; it’s like a golden ticket to Willy Wonka, I swear. When I started this, it wasn’t like this,” said Orlee Weisberg, founder of Denim By Orlee. Weisberg sells vintage jeans — not solely Levi’s, but mostly — via an e-commerce site dubbed denimbyorlee.com. The site launched in 2018, but for three years prior, Weisberg sold jeans out of the back of her car, with women trying them on in coffee shop bathrooms, she said. Her denim sells for $200-$300, with shorts ranging from $140-$188.
Weisberg has 32,000 Instagram followers, who regularly see influential women wearing the vintage denim she sources. They include Hailey Bieber, Kylie Jenner, Kourtney Kardashian and Matilda Djerf. She’s never paid for PR or marketing, and attributes Bieber wearing her denim to the stylist Emily Lafitte — though she’s not even sure how it happened, she said.
According to Dash Social’s listening tool, Levi’s mentions remained steady from May 2024 through February 2025, then tripled from February 2025 to April 2025, peaking at above 50,000 mentions across Instagram, Twitter and YouTube. This was not however, specific to vintage Levi’s and could certainly take into account cultural factors like the Beyoncé song “Levii’s Jeans,” released on the “Cowboy Carter” album in March 2024.
Still, for Weisberg, business speaks for itself. Weisberg sells her vintage denim as is, without added tailoring or embellishments. “I have always loved the idea [that] this is how it was born,” she said. “My customer has the right to do whatever they want to the denim after they buy it, [but] I like to give them the opportunity to have it [as it was]. I love that there’s a story behind it,” Weisberg said.
Other popular vintage purveyors take a different approach, which may be good for those not blessed with a Bieber body. With Love Lenny (253,000 Instagram followers) has a shop in Studio City, Los Angeles, where founder Lindsey Davidson Paley takes one-on-one appointments to help clients pick their perfect pair of vintage denim. She then custom-tailors them to precisely fit their body. Davidson Paley takes the whole production on the road once a month to bring these appointments to women in other cities; she just wrapped up a five-day NYC pop-up. Jeans are $425 and shorts are $365. Prices can go up if customers add embroidery, for example.
Lenny was born out of a lay-off during Covid. Now, four years, founder Lindsey Davidson Paley has fashioned herself as a go-to expert of vintage denim fit. She appreciates the circularity and sustainability factor of vintage denim — specifically, “not having to create my own [thing], but instead taking something that was someone else’s and making it into something [new],” she said.
Initially, when she started selling vintage denim, her customers often failed to find a perfect fit and constantly said they were going to get the jeans altered. That’s when the idea was born to combine the two offerings — vintage jeans and custom-tailoring — into one business. Posts like this one from Tinx (1.5 million TikTok followers), in which the influencer wearing Lenny says, “This is the best my ass has ever, and probably will ever look,” have been a boon to the business, Davidson Paley said. Though she has a smaller following, Brittany K. Sansone (52,000 Instagram followers) has also directed many of her followers to Lenny. Sansone’s bio reads “Vintage Levi’s addict.”
When asked why she thinks vintage denim is so popular right now, Davidson Paley pointed to the popularity of the quiet luxury moment. “There are always going to be people who like logo-mania, Balenciaga, Chanel, etc. But the majority of fashion girlies really want that understated but polished look, and vintage Levi’s are the O.G. They’re tried-and-true, they’re never going away,” she said. “The coolness factor, the individuality of it being vintage and the perfect fit is a match made in heaven.”
For her part, Ali Grace of Shop Ali Grace started her vintage denim brand in 2018, after graduating college. She sells through an e-commerce site, shopaligrace.com, and also through wholesale channels. Ali Grace launched on Revolve in May 2023 and FWRD in October the same year. In March 2025, Shop Ali Grace launched at Anthropologie. Like both Davidson Paley and Weisberg, Grace has seen the impact of influencers on her business. In fact, it was a post by Kelsey DiPrima (134,000 Instagram followers) spotlighting Grace’s business that caught the attention of the Revolve buyer she now works with.
Like Davidson Paley, Grace customizes vintage denim, but her business model is different. For example, one of Grace’s most popular items is her customized barrel jeans ($398), which are made by deconstructing and reconstructing two pairs of vintage Levi’s. Another Ali Grace signature is the Allysa jean, which features tilted butt pockets ($378).
“The beauty of vintage is there’s inherent value regardless, [even prior to customization],” Grace said. Before she started working with seamstresses, she’d spend hours looking for vintage pairs that just happened to best align with a client’s measurements. Though that is no longer logistically possible, customized jeans are still available for order, and Shop Ali Grace’s website guides clients through taking their own measurements. The jeans that are sold wholesale have been reworked to match modern conventional sizing.
It used to be that shoppers could find vintage denim on their own at their local Goodwill, Grace said. But, likely due to the spike in demand, that is no longer the case. “Now, it’s mostly modern denim that is sold. … Those paper-tags, made-in-the-USA, 20- to 30-year-old, real vintage Levi’s are really hard to find in thrift stores, [whereas] wholesalers have pallets and pallets of true vintage jeans and the styles that I’m looking for: 505s and 501s,” she said. However, she noted that she sources from all of Levi’s series, as the jeans can all be repurposed for other products her brand now creates.
It is the combination of offering customers something unique while also curating the selection for them is makes her business work, Grace said. “Gen Z is beyond fast fashion. They take pride in what they’re wearing,” she said. “For me, the hunt of finding vintage is part of what I love about it so much.” For those who don’t have time to hunt, her website has it ready-to-go, she said.
The history of these pieces is also a draw. “It’s so cool to be able to be like, these jeans could have been worn by a supermodel or a farmer or a metal worker or a painter,” Grace said. “They could have been a famous person’s pants. … I have found receipts from Paris in my pants. I’ve found movie tickets from the ’70s, old money. It’s so cool, you know?”
Pop-up of the week: Form takes NYC
Form, the popular digital workout platform and activewear brand, is hosting a shopping and fitness pop-up this weekend in Union Square. Fans of the workout platform, which Glossy recently reported would finish 2024 having earned $12 million in revenue, will have the chance to work out with co-founder and trainer Sami Clarke Barnett IRL. They can also shop the brand’s clothes, typically only sold on its website, and get first dibs on the next collection launch.
“The Form experience is more than a pop-up — it’s our brand brought to life, our mission made tangible and our community at the center of it all,” Clarke Barnett told Glossy.
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