Roselyn – Orthopedic Comfort Flats – Jennifer & Madison New York

Name: Roselyn – Orthopedic Comfort Flats
Brand: Jennifer & Madison New York
Price: 54.95 USD
Availability: InStock

$54.95 $110.00 Save 50%

Free Shipping across the U.S.

30-Day Money-Back Guarantee

More than 150,000 satisfied customers

Only a few items left!

Ships on

Free

ONE YEAR ANNIVERSARY SALE — LAST DAY: Due to high demand, only a limited number of items remain at this price. We're celebrating 10 years in New York and everyhting is on sale today only. If you can still click "Add to Cart," it's still available.

Roselyn brings a timeless, feminine silhouette together with supportive, day-long comfort — a lightweight orthopedic flat designed for effortless wear. The soft upper gently adapts to your foot, while the adjustable strap keeps everything secure without pressure. Finished with a cushioned insole and flexible sole, it’s the perfect blend of classic simplicity and practical support.

Why you’ll love it

Orthopedic cushioned insole – reduces foot fatigue and supports natural alignment
Lightweight flexible sole – absorbs impact and makes every step feel softer
Adjustable strap design – ensures a secure fit without tightness
Classic Mary Jane style – elegant, versatile, and easy to pair with everyday outfits

A shoe created for women who value comfort as much as simplicity — soft, supportive, and ready for every step of your day.

If our product does not meet your expectations, you may return it within 30 days of receiving your order.

Before returning an item, please contact our customer service team at info@jenniferandmadison.com and let us know the reason for the return so we can process your request correctly.

We offer free shipping on all orders within the United States.

All packages include tracking, so you can monitor your order at any time.

You will receive your tracking information by email within 1–24 hours after placing your order.

Our customer service is available 24/7 to answer all your questions and comments.

Whether you need advice on a product or help with an order, we are here to support you.

Don’t hesitate to contact us; we’re happy to help!

Please contact us at info@jenniferandmadison.com

Rachel K. and 2.7k+ other women love Jennifer & Madison New York!

{"id":53499827126610,"title":"Black \/ 5","option1":"Black","option2":"5","option3":null,"sku":null,"requires_shipping":true,"taxable":false,"featured_image":{"id":70755393143122,"product_id":10795768119634,"position":1,"created_at":"2026-05-19T12:42:34-04:00","updated_at":"2026-05-19T12:42:37-04:00","alt":null,"width":1080,"height":1080,"src":"\/\/jenniferandmadison.com\/cdn\/shop\/files\/imgi_13_Saadf06b65f304911a37140e7eb0d69b3F_720x-Photoroom.jpg?v=1779208957","variant_ids":[53499827126610,53499827159378,53499827192146,53499827224914,53499827257682,53499827290450,53499827323218]},"available":true,"name":"Roselyn – Orthopedic Comfort Flats - Black \/ 5","public_title":"Black \/ 5","options":["Black","5"],"price":5495,"weight":0,"compare_at_price":11000,"inventory_management":null,"barcode":null,"featured_media":{"alt":null,"id":58343427866962,"position":1,"preview_image":{"aspect_ratio":1.0,"height":1080,"width":1080,"src":"\/\/jenniferandmadison.com\/cdn\/shop\/files\/imgi_13_Saadf06b65f304911a37140e7eb0d69b3F_720x-Photoroom.jpg?v=1779208957"}},"requires_selling_plan":false,"selling_plan_allocations":[],"quantity_rule":{"min":1,"max":null,"increment":1}}

What Our Customers Say

Trusted by thousands of happy customers

★★★★★

4.9 Based on 2,753 reviews

★★★★★

“The floral print is absolutely beautiful and the fit is very forgiving. I love how easy it is to dress up with sandals or wear casually during the day. It quickly became one of my favorite summer dresses.”

Deborah S.

★★★★★

“I bought these for a vacation and ended up wearing them the entire trip. They provide wonderful support while still looking stylish. The lightweight feel makes them perfect for long walks and warm weather.”

Carol W.

★★★★★

“These slip-ons are exactly what I was looking for. Easy to put on, lightweight, and comfortable enough for daily wear. I wear them almost every day and my feet still feel great by the evening.”

Barbara T.

★★★★★

“The Nora dress arrived just before a family gathering and quickly became my favorite outfit. The fabric feels soft and breathable, the fit is flattering, and I've already received several compliments every time I've worn it.”

Patricia R.

★★★★★

“I've tried many sandals over the years, but these are by far the most comfortable. The support is excellent, they fit perfectly, and I was able to walk around town all afternoon without any discomfort. Jennifer & Madison New York truly exceeded my expectations.”

Susan M.

★★★★★

“This dress looks even better in person. The off-shoulder design feels elegant without being uncomfortable, and the material flows beautifully when walking. It feels like a much more expensive dress than it”

Linda K.

★★★★★

“The Serenella dress arrived two days before a special dinner and I had already worn it twice by the weekend. The fabric drapes beautifully, feels light on the skin, and is comfortable enough to wear all day long.”

Julie M.

★★★★★

“I wasn't sure about the halter style at first, but I'm so glad I ordered it. The gathered details create a flattering shape and the dress feels comfortable from morning to evening. Wonderful quality from Jennifer & Madison New York.”

Nancy B.

Combine and get up to 20% extra off

View all

Save 65%

Mirelle | Gathered Halter Midi Dress

$199.95 $69.95

Save 57%

Calen | Off Shoulder Flow Midi Dress

$189.95 $79.95

Save 65%

Isel | Soft Wrap Maxi Dress

$199.95 $69.95

Save 64%

Virel | Relaxed Floral Midi Dress

$184.95 $64.95

View all
28 products

Jennifer & Madison

Ten Years Ago, Two Best Friends Had a Dream

Some of life's biggest journeys begin with the smallest moments — a conversation over coffee, a shared idea, a dream that feels a little too big to say out loud.

Ten years ago, that's exactly how Jennifer & Madison New York began. Just two best friends with a love for timeless fashion and a belief that every woman deserves to feel confident, beautiful, and comfortable in what she wears.

What started as a simple dream became something far greater than we ever imagined. We've celebrated milestones, packed thousands of orders, and heard from incredible women who told us our pieces helped them feel like themselves again.

Because Jennifer & Madison was never just about clothing. It was about confidence, elegance, and helping women feel their best every day.

Today, we're celebrating ten wonderful years with our biggest anniversary sale yet. None of it would have been possible without you — every order, every message, and every customer who chose to be part of our journey.

To thank you, we're offering our largest discounts of the year before these pieces are gone.

If something catches your eye, don't wait too long. The best moments have a way of passing faster than we expect.

With love,
Jennifer & Madison New York ❤️

FAQs

Yes, only today we offer free shipping on all orders. No hidden fees, no surprises at checkout. You'll see the full breakdown before you pay.

Once your order is confirmed, you’ll receive an email with your order number and tracking details.

You may return items within 30 calendar days of receiving your order.

Our products are designed to fit true to size. You can find a detailed size chart on each product page to help you choose the perfect fit with confidence.

📧Email: info@jenniferandmadison.com

30-DAY MONEY-BACK GUARANTEE

We offer a 30-day return policy. Feel free to return any item within 30 days if you are not completely satisfied.

FREE DELIVERY

We offer free shipping with tracking throughout the United States.

SECURE PAYMENT

At Jennifer & Madison New York, we offer secure and convenient payment options, including credit cards.