Chessa - Chelsea Boots

$374.95 USD $74.95 USD Save Today 80%
/
50% OFF
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  • 30 days money-back guarantee
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.

Step Into Timeless Elegance with the Chessa Chelsea Boots

The Chessa Chelsea Boots are designed for the woman who does it all, blending elegance, function, and comfort in one seamless look. Say goodbye to stiff fits, fading fabrics, and pieces that just don’t feel right—this essential pair delivers a flattering fit, lasting structure, and day-long comfort that won’t quit.

Chessa Chelsea Boots

Why You’ll Love Chessa Chelsea Boots:

  • Confidence Through Style: A sculpted design that enhances your silhouette and elevates your look instantly.
  • Authentic All-Day Comfort: Lightweight and flexible, they move with you while keeping softness and ease.
  • Effortless Versatility: Seamlessly transitions from weekdays to weekends, pairing perfectly with any wardrobe.

Order now—limited quantities available and selling fast!

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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35 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.