WINDSOR™ | Casual Comfort Ankle Boots

$234.95 USD $69.95 USD Save Today 70%
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50% OFF
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Only 6 in stock
ANNIVERSARY SALE: Celebrate our Anniversary Sale with up to 70% off. Many styles are offered in limited quantities for this event, and once they’re gone, they will not return. If “Add to cart” is visible, your size is still available – but not for long.

Stylish Comfort in Every Step with Windsor™ | Casual Comfort Ankle Boots

The Windsor™ Casual Comfort Ankle Boots blend simplicity with a stylish edge, offering the perfect combination of comfort and versatility. Whether you’re running errands, at work, or enjoying a laid-back day out, these boots are your go-to choice for effortless, casual wear. Made to keep you on your feet comfortably, they offer durability without compromising style.

Why You'll Love the Windsor™ Casual Comfort Ankle Boots

✔ Durable and Resilient: Built for daily wear, these boots are designed to last, making them a practical and long-lasting addition to your wardrobe.

✔ Convenient Side Zip Closure: With an easy side zip, these boots are simple to slip on, perfect for those always on the go.

✔ Flexible, Non-Slip Sole: The sturdy, non-slip soles provide excellent grip, keeping you stable on a variety of surfaces.

✔ Lightweight and Breathable Material: Crafted from eco-friendly leather, these boots are lightweight, breathable, and designed to keep your feet comfortable throughout the day.

✔ All-Day Comfort: Made for everyday use, these boots offer a comfortable fit that lets you wear them all day without any discomfort.



 

We like to keep it simple – enjoy free delivery anywhere in the USA, no matter the size of your order.

Our friendly customer care team is here to help with any questions or advice about your order. Whether you need style tips, sizing guidance, or help with delivery, we’re just a message away.

We want you to love your purchase. If you’re not completely happy, you can return it within 30 days of receiving your order for a full refund – no hassle, just peace of mind.

Mary M. Verified badge and 16k+ other women love Eleanor & Grace.

Combine & get an extra 10% off

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15 products

Costumers love Eleanor & Grace

<h2><strong>Costumers love Eleanor & Grace</strong></h2>

I took a chance on these boots during the Anniversary Sale and I'm so glad I did. The quality is even better than I expected and they're surprisingly comfortable right out of the box. They look amazing with skirts and I can already tell I'll be wearing them constantly.

Melissa Harper, Charlotte NC

<h2><strong>Costumers love Eleanor & Grace</strong></h2>

These boots are exactly what I was looking for. They fit perfectly with jeans and are so comfortable I've been wearing them around the house just because. I'm already eyeing another pair in brown.

Rachel Stevens, Columbus OH

<h2><strong>Costumers love Eleanor & Grace</strong></h2>

The packaging alone made me feel like I was treating myself to something really special. These boots are even more beautiful in person and so comfortable I wore them around the house for an hour before I could take them off. I'm already planning my next order.

Ashley Martin, Seattle WA

<h2><strong>Costumers love Eleanor & Grace</strong></h2>

I wasn't sure about ordering boots online, but these exceeded my expectations. They fit perfectly and were surprisingly comfortable right out of the box. I wore them to dinner last night and felt so put together and confident.

Linda Thompson, Portland OR

<h2><strong>Costumers love Eleanor & Grace</strong></h2>

These ankle boots are exactly what I needed for everyday wear. The heel height is perfect for running errands or meeting friends for lunch, and they look so polished with jeans. I've gotten more use out of these in one week than most shoes I own.

Diana Mitchell, Austin TX

30-Day Money Back Guarantee

At Eleanor & Grace, we take pride in every piece we offer, and we’re confident you’ll love your purchase as much as we do. That’s why we provide a simple, risk-free 30-day money-back guarantee. If for any reason you’re not delighted, simply return your item within 30 days for a full refund — no fuss, no worries.

Celebrating 20 Years With You

What started in 2005 as a tiny dream between two best friends in their twenties has grown into something we never could have imagined, a brand loved by women all across the country.

20 years later, we’re still best friends, still doing what we love, and more grateful than ever for the community that has grown with us. To celebrate this incredible journey, we’re saying thank you with up to 70% off during our Anniversary Sale.

With love
Eleanor & Grace

What Our Shoppers Ask Most

We know that body shapes can change over time. That’s why we provide clear size guides and detailed fit notes for every piece — and we’re always here to help personally via email if you need extra guidance.

At Eleanor & Grace, we believe in elegance without an expiry date. Our collections are refined, feminine, and timeless, so you’ll never feel like you’re chasing trends — only wearing styles that truly suit you.

Our fabrics are carefully chosen with America’s seasons in mind — from breathable, lightweight merino to soft cottons and versatile viscose blends. You’ll stay comfortable and stylish, whether it’s a sunny afternoon in California or a breezy evening in New England.

Clothing should lift you up, not hide you away. Our silhouettes are thoughtfully designed to flatter and highlight your natural elegance, so you feel beautiful and confident — from New York to California.