★★★★☆
★★★★★
4.7/5 | Based on 1200+ Reviews

Hailey | Orthopedic Leather Boots

$159.95 $74.95 SAVE 53%

Free Shipping with UPS

30-Day Money-Back Guarantee

Low in stock. Only 4 left.

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UPDATE: Due to high demand during our Anniversary Sale, only a few units are left in stock!

Comfort That Supports You All Day Long

If pain, swelling, or instability slow you down, these supportive, orthopedic-approved essentials are your answer. Our Leather Knee-High Boots are cushioned, wide-fit, and beautifully stable—handcrafted by trusted makers and handpicked by me & my daughter to last for years. Dress them up or down; Hailey | Orthopedic Leather Boots bring comfort you can actually feel without sacrificing style. Reach for Leather Knee-High Boots whenever you want effortless polish and pain-free steps.

Why Women Love the Leather Knee-High Boots

  • Pain-free walking — reduces pressure on heels and forefoot now.
  • Shock absorption — plush insole softens every step immediately.
  • Wide-fit comfort — gentle room for swelling without pinching.
  • Orthopedic support — arch and ankle stability you can rely on.
  • Non-slip balance — steady traction for confident strides.

We keep it simple: Free US Shipping, 30-Day Hassle-Free Returns, and a 100% Money-Back Guarantee. Because each pair is handpicked and crafted in small batches, Leather Knee-High Boots are selling quickly—once they’re gone, restocks take time. If Hailey | Orthopedic Leather Boots feel right, secure your size today and step into lasting comfort with quality you’ll wear for seasons to come.

At Jane & Claire Vermont, customer satisfaction comes first. That's why we keep you constantly updated on your order and always offer free shipping. We use the reliable delivery services of UPS.

Trusted by thousands of women - If for any reason you’re not happy with your order, simply send it back within 30 days. Shopping with us is worry-free.

We offer a range of secure and convenient payment methods to make your shopping experience seamless. Here’s what we currently accept:

  • Credit or Debit Cards: We welcome all major credit and debit cards, including Visa, Mastercard, and American Express.
  • Mobile Payment Services: You can also use Apple Pay, Shop Pay, or Google Pay for a quick and easy checkout.
  • Gift Cards or Store Credit: Have a gift card or store credit from us? You can use it towards your purchase.

Customers love Jane & Claire VERmont

<h2>Customers love Jane & Claire VERmont</h2>

Clothes fit true to size

"I always worry about sizing online, but this one was spot on. The fit was perfect and the length just right. Arrived quickly too."

Margaret Hill

<h2>Customers love Jane & Claire VERmont</h2>

Lovely and warm 🤍

"I was pleasantly surprised by how soft and cozy this coat feels. The fit is just right for me, and the sleeves are a nice length too. It has a relaxed look but still feels elegant enough to wear out. I’ve already had compliments on it!"

Jill Whitaker

<h2>Customers love Jane & Claire VERmont</h2>

Bright and Cheerful

“I love how vibrant and uplifting this blouse feels. The fabric is soft and light, and the fit is just right — not too tight, not too loose. It instantly brightens up my outfit and always gets compliments when I wear it.”

Valerie Harmon

<h2>Customers love Jane & Claire VERmont</h2>

Quickly delivered

"I was a little worried about delays, but my package arrived in just 2 days. Super fast!"

Emily Johnson

<h2>Customers love Jane & Claire VERmont</h2>

Elegant and Effortless

“This blouse feels so soft and light, and the fit is just right — relaxed but still flattering. I love the rich colors, they make me feel polished even when I’m just having coffee at home. It’s quickly become one of my favorites.”

Connie Delaney

<h2>Customers love Jane & Claire VERmont</h2>

So Comfortable and Stylish

“I was pleasantly surprised by how comfortable these shoes are. The fit is perfect for my feet, and they feel supportive even after long walks. They have a relaxed, casual look but still feel stylish enough to wear out. I’ve already received a few compliments on them!”

Marianne Briggs

<h2>Customers love Jane & Claire VERmont</h2>

Exactly what I needed

"This fit is perfect and the fabric feels so soft. Very happy with the quality, will definitely order again."

Olivia Smith

<h2>Customers love Jane & Claire VERmont</h2>

Elegant and Comfortable

“These shoes are incredibly comfortable yet look so polished. The fit is just right, and they feel supportive even after wearing them all day. They add a touch of elegance to any outfit, and I’ve already had people asking where I got them.”

Connie Delaney

<h2>Customers love Jane & Claire VERmont</h2>

Favorite

"This is the kind of piece you end up reaching for again and again. Just easy to wear."

Jill Whitaker

<h2>Customers love Jane & Claire VERmont</h2>

Super fast delivery

"I ordered on Monday and it arrived the next day! Really impressed with the service and the packaging was lovely too."

Sophia Williams

<h2>Customers love Jane & Claire VERmont</h2>

I wasn’t sure about ordering online… but it went perfectly.

"I’m usually careful with online shopping, but everything here felt safe and simple. My order came two days later and the dress fit beautifully. I’ll be coming back for sure."

Susan Miller

<h2>Customers love Jane & Claire VERmont</h2>

So comfortable and easy to wear

"These boots are soft inside but not heavy at all. They fit perfectly and feel comfortable right from the first step. I’ve been wearing them around the house and out for errands, they go with everything."

Helen Roberts

<h2>Customers love Jane & Claire VERmont</h2>

So comfortable and flattering

"Feels amazing on my skin and fits just right. Haven’t felt this confident in a while!"

Isabella Brown

<h2>Customers love Jane & Claire VERmont</h2>

Return process was easy too

"I ordered two pairs of shoes to try the sizes. Both arrived quickly and looked even nicer than I expected. One pair didn’t fit quite right, so I sent it back, the return was simple and my refund came within a few days. Very reassuring experience."

Barbara Reed

<h2>Customers love Jane & Claire VERmont</h2>

Light and Perfect for Walks

“This blouse feels so airy and comfortable — perfect for a stroll through the park. The colors are cheerful without being too bright, and the fit gives me enough room to move freely. I always feel put-together yet relaxed when I wear it.”

Carmen Doyle

<h2>Customers love Jane & Claire VERmont</h2>

Perfect for the upcoming autumn season🍁

"This sweater is so cozy and soft, and I love the colors — they feel cheerful but still subtle. The fit is relaxed without being too loose, and it’s warm enough for a walk outside on a crisp fall day. I’ve had several compliments already!"

Valerie Harmon

CELEBRATING 10 YEARS OF COMFORT AND STYLE

I, Jane – started this little store as a mom, just hoping to support my daughter Claire.

There were tough days – nights I wasn’t sure how I’d make it. But with every order, you helped me provide for her… and build something bigger than I ever imagined.

Today we celebrate our store anniversary & this is my way of saying thank you. For being part of our journey, our growth, and our story. ❤️

With love, 
Jane and Claire

JANE & CLAIRE VERMONT

TIMELESS COMFORT, SEASONAL STYLE

Born in the heart of Vermont, our collections bring together warmth, softness, and effortless elegance. Each piece is thoughtfully crafted to flatter real women’s lives — from cozy mornings to evenings out.

With 10 years of comfort and style behind every design, Jane & Claire invites you to dress with confidence and ease, every single day.

Frequently Asked Questions

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

Orders are typically processed within 3 business days after being placed.

Once your order has been shipped, you will immediately receive a confirmation email, which includes a link to your personal tracking information so that you can stay informed about the status of your orders at all times.

Yes, We offer a 30-day money-back guarantee.

Trusted by thousands of women - If for any reason you’re not happy with your order, simply send it back within 30 days. Shopping with us is worry-free.

FREE SHIPPING

Orders in the United States are always shipped for free and insured with track & trace.

30-DAY MONEY-BACK GUARANTEE

At Jane & Claire, you can shop with peace of mind thanks to our 30-day money-back guarantee. Simply return your items within 30 days.

SECURE CHECKOUT

At Jane & Claire you can securely and conveniently pay for your order using Credit Card.

Free Shipping

We offer Free Shipping for maximum customer comfort. Your satisfaction is important to us, which is why we offer smooth and free delivery.

30-Day Return Guarantee

Your satisfaction is our focus. Our 30-day return policy guarantees you maximum flexibility and the best shopping experience.

100% Secure Payment

We offer you a variety of secure payment options. Pay easily and enjoy a safe shopping experience.