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CLEARANCE SALE UPDATE: Due to high demand during our clearance sale, only a limited amount of units are left! If you can still click 'Add to cart' it’s still available

Feel empowered in shoes that never sacrifice comfort for style

Discover classic retro elegance with the Olivia Mary Jane Orthopedic Shoes, where nostalgic charm meets modern support. Featuring a rounded toe, low-profile sole, and secure strap, Olivia™ blends timeless vintage appeal with everyday comfort—ideal for women who want to stay graceful, mobile, and pain-free from morning to night.

Maximum Comfort: These orthopedic shoes feature a cushioned insole and soft lining that reduce pressure on the heel, arch, and forefoot—perfect for easing plantar fasciitis, bunions, or daily foot fatigue.
Greater Stability for an Active Lifestyle: The adjustable buckle strap and low, supportive sole ensure a secure fit and improved balance, giving you confidence with every step.
For Wide and Narrow Feet: Made with lightweight, breathable vegan leather, Olivia™ adapts comfortably to both narrow and wider foot shapes, keeping your feet cool and supported all day long.

Specifications

Material: Soft premium leather with a soft finish
Sole: Cushioned, orthopedic insole with low block heel and anti-slip rubber outsole
Fit: Wide Fit, Please choose 1 size up for an optimal fit.

Not happy with your order? Not to worry! We stand by the quality of our products.

If you are not satisfied with your purchase for any reason, you can return it always for a full refund or exchange.

Have questions about shipping? We’re here to help! Send an email out to our customer support team info@madisson-newyork.com

Order before 23:59 and we will send by tomorrow!

Making sure you receive assistance is a top priority for us!

If you still need help, we are available 24/7!

Reach out to our dedicated customer support team at the 'contact us' page

or email us at info@madisson-newyork.com

We're here to help with any questions or concerns you have.

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WHY CUSTOMERS 💗 Madisson

Excellent

4.8

/ 5

1,634+ reviews from satisfied customers.

such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet too, they really care about their customers 🥰 such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet... such a cute boutique!! love how unique the styles are, and the quality is amazing. the owners are so sweet too, they really care about their customers 🥰

✔ Maddie L. | 01/10/2025

first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super fast. def coming back for more!! 🤩 first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super... first time ordering & WOW, i’m impressed! the fabric is soft, the fit is spot on, and it arrived super fast. def coming back for more!! 🤩

✔ Chloe S. | 03/01/2025

These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online, but I’m so glad I did. The fit is perfect, and they’ve quickly become my go-to pair for everyday wear. These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online,... These mary janes are fantastic. They’re stylish, comfortable, and really well made. I was a bit hesitant to order online, but I’m so glad I did. The fit is perfect, and they’ve quickly become my go-to pair for everyday wear.

✔ Lori B. | 12/08/2024

Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the style is even better in person. Highly recommend! Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the... Beautifully made and very comfortable. I was worried about ordering shoes online, but they fit perfectly. Great quality, and the style is even better in person. Highly recommend!

✔ Amelia W. | 01/14/2024

i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch and got so many compliments 🥰 i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch... i never write reviews but omg these boots?? so lightweight, so comfy, and they look amazing!! wore them to brunch and got so many compliments 🥰

✔ Sienna J. | 02/09/2024

had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and helpful, they really care about their customers. such a rare find these days 💕 will 100% be shopping here again! had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and... had to exchange for a different size and wow, the process was sooo easy!! the owners were so kind and helpful, they really care about their customers. such a rare find these days 💕 will 100% be shopping here again!

✔ Holly T. | 12/20/2025

A FINAL FAREWELL

Hi, I’m Isabelle — founder of Madisson New York.

After many beautiful years, I’m closing the boutique as my mother Grace is beginning to grow older and seriously unwell, and it’s time for me to care for her.

With a heavy heart, I’m holding our Final Sale — up to 70% OFF to clear everything out. Once an item is gone, it will not return.

💗 Thank you, truly, for all your support.

Back to Orthopedic Shoes

Frequently Asked Questions

We know how tricky sizing can be — especially if you have wider feet or deal with bunions or foot pain. At Madisson, our shoes are true to size and designed with comfort in mind. You’ll also find real fit tips and customer reviews on every product page. Still unsure? Our team is just an email away.

Of course! Once your order leaves our warehouse, we’ll email you a tracking link so you can follow it every step of the way. We’re always here if you need help along the journey

Yes, standard shipping is completely free within the United States — no hidden fees, just comfort delivered to your door.

You can pay safely with any major credit card. Your payment is 100% secure and fully insured — so you’re always protected.

We design for women who value comfort and style. Our shoes & sandals are lightweight, supportive, and flattering — perfect for daily walks, family outings, or just feeling confident at home. Thousands of women trust Madisson because we truly understand what your feet need.

We believe in our shoes — and we believe in earning your trust. That’s why Madisson offers a lifetime return policy. If your shoes don’t feel quite right, even after weeks or months, you can return them — no pressure, no deadline. We’ll make it right.