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Why Every It-Girl Is Obsessed With Lenny’s Custom Vintage Denim (And How You Can Get the Same Booty-Boosting Magic)
If you’ve scrolled Instagram lately and thought, “How does everyone suddenly have the most flawless, lived-in vintage jeans?” — the answer is Lenny.
Tucked away in Studio City, California, Lindsey Davidson-Paley’s appointment-only outpost has become the denim equivalent of a secret society. Rachel Bilson, Whitney Port, Hannah Berner, Carole Radziwill, Katie Lowes, Tinx, and a constantly growing list of celebrities and influencers are all walking around in perfectly worn-in Levi’s, Wranglers, Lees, and rare European deadstock — each pair tailored exactly to their body like it was sewn for them yesterday.
Lindsey’s love affair with denim started young. “I was a total tomboy growing up and practically lived in jeans,” she told Entertainment Tonight. “When it came time to build my own brand, vintage felt like the only authentic path. Every pair has a story — the whiskering, the fading, the tiny imperfections. That’s the romance. No two are ever the same.”
What sets Lenny apart isn’t just the sourcing (though the curation is insane — think buttery ’90s 501s, hard-to-find Wrangler flares, and European gems you won’t see anywhere else). It’s the customization. During your one-on-one appointment — in-person in LA or virtual from literally anywhere — Lindsey and her team tweak the waist, hips, seat, and even add hand-embroidery, all while preserving the original character of the denim.
“Everyone wants their booty to look good,” Lindsey laughs. “A little strategic shaping in that area changes everything. There’s truly no better confidence boost than sliding into jeans that feel like they were made for your body.”
And celebrities agree. Hannah Berner posted her Lenny jeans with the caption “These jeans cured my depression.” Carole Radziwill has been spotted in her custom pair on repeat. Whitney Port called them “the most flattering jeans I’ve ever owned.” Even Tinx famously declared on TikTok, “This is the best my ass has ever — and probably will ever — look.”
The best part? You don’t need a celebrity budget or connections. Appointments start with vintage pairs from around $300–$600 (depending on rarity), and tailoring/embroidery is included. Lindsey’s golden rule: “Start with a size close to your actual measurements. Going up three sizes only works if you specifically want the baggy look. Otherwise, we keep the integrity of the original silhouette and just make it hug you perfectly.”
In an era of fast-fashion denim that pills after three wears, Lenny is the sustainable, soulful antidote. Every pair is upcycled vintage — zero new cotton, zero waste, maximum personality. As Lindsey puts it: “We’re not just selling jeans. We’re solving the universal problem of jean shopping trauma and giving women denim they’ll wear for the next decade.”
Ready for your own “best ass ever” moment?
→ Book your in-person or virtual appointment at withlovelenny.com → Follow along on Instagram @withlovelenny for new drops and client transformations
Spots fill up fast (especially after every new celebrity post), so don’t sleep on this.
More denim inspiration:
- The Best Elevated Basics to Refresh Your Closet
- How to Dress Like a Cowboy: 5 Outfits and Style Tips
- Top Western Wear Jackets, Boots & More – Black Friday Deals 2025
- Summer-Ready Finds from the Saks Designer Sale
(Original story via Entertainment Tonight – read the full interview here)