Lucky Penny Vintage

08/13/2026

Join us in welcoming Lucky Penny Vintage to their new location in downtown Madison!

✂ Ribbon Cutting Ceremony
📅 Friday, September 4th | 12:00 PM
📍 225 E. Main Street, Madison, IN

Founded by Ashley Wells, Lucky Penny Vintage offers a thoughtfully curated collection of vintage and pre-loved clothing, accessories, and unique finds. What began as a series of pop-up shops in 2024 has continued to grow, fueled by Ashley’s passion for sustainable fashion and her eye for distinctive pieces that give shoppers the chance to find something truly their own.

And of course, it wouldn’t be Lucky Penny without Penny, Ashley’s pug and the beloved face (and namesake!) of the brand.

Come browse the racks, explore the new space, and join us as we cut the ribbon on this exciting next chapter for Ashley, Penny, and Lucky Penny Vintage!

08/08/2026

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07/20/2026

06/27/2026

Come see us at Madison Pride 2026 12pm - 5pm
Shops also open till 6pm!

06/22/2026

New Member Spotlight: Lucky Penny Vintage 🎉

We’re excited to welcome Lucky Penny Vintage to the Madison Area Chamber of Commerce!

Founded by Ashley Wells, Lucky Penny Vintage began as a series of pop-up shops in 2024 before finding its home inside Circe Society Artists in downtown Madison. Today, the shop offers a thoughtfully curated collection of vintage and pre-loved clothing, accessories, and unique finds for shoppers who love timeless style and one-of-a-kind pieces.

What sets Lucky Penny Vintage apart is Ashley's passion for sustainable fashion and her eye for distinctive pieces that help customers express their personal style while giving quality clothing a second life. Whether you're searching for a vintage staple, a statement piece, or your next favorite outfit, there's always something new to find.

Be sure to stop in and browse Ashley's carefully curated collection of vintage and pre-loved fashion!

06/13/2026

Lucky Penny summer hours:

Friday–Saturday 11–6
Sunday 12–4

Come by, meet the interns, check out what’s new in the gallery, and dig through some vintage.