Stridewell – Square-Heel Zip-Up Ankle Boots

Stridewell – Square-Heel Zip-Up Ankle Boots

Light Brown / 5.5
Sale price  $59.99 Regular price  $119.99 Save 50%
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Stridewell – Square-Heel Zip-Up Ankle Boots
4.7 / 5 Rated (+5,172 reviews)

Stridewell – Square-Heel Zip-Up Ankle Boots

Sale price  $59.99 Regular price  $119.99 Save 50%
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Almost Sold Out!
SUMMER SALE UPDATE: Inventory is low. If you can still click Add to Cart, your size is available. — Hollis & Pearl

Boots That Stay Comfortable From Morning To Night

Some mornings you just want to put on one pair and be done. These are those boots.

The low square heel spreads your weight instead of pushing it onto your toes, so standing and walking all day feels easy.

A padded arch-support insole sits under a grooved rubber sole — comfort you feel, not just a promise on a tag.

Cozy indoors, steady on a damp sidewalk, and they look right with what you already own.

Rubber Sole With A Grooved Tread, Built For Wet Pavement

Stand all day without aching feet
The low square heel keeps your weight balanced instead of crushing your toes. Your feet feel the difference by hour four.

One pair, no shoe swap needed
Wear them from the kitchen to a long afternoon walk. No spare flats in your bag, no changing under your desk.

Arch support built right in
A padded insole with real arch shape means comfort isn't a guess. Most boots leave this out and hope you won't notice.

Steady footing on wet sidewalks
The grooved rubber sole grips damp pavement and fallen leaves. Walk at your normal pace instead of tiptoeing.

Goes with everything already in your closet
Clean round toe, smooth side zip, neutral finish. Eight colorways, so there's one that works with your jeans and your dress pants both.

What you get today

  • Stridewell ankle boots, one pair
  • Padded arch-support insole for all-day standing and walking
  • Grooved rubber outsole for grip on wet pavement
  • Smooth side zip — on and off in seconds
  • Free tracked shipping
  • 30-day money-back guarantee

Seasonal production run — once this batch sells out, restock pricing may change.

Bring Stridewell into your closet today and step into boots that stay comfortable from morning to night.

Try Stridewell at home for 30 days. If they don't fit, look right, or wear the way you expected, return them for a full refund.

30-day at-home trial
Try Stridewell at home for 30 days. If they don't fit, look right, or wear the way you expected, return them for a full refund.

Frequently asked questions

Can I wear these with thick socks?
Yes. The round toe box leaves room for a regular wool sock without pinching. Measure your foot length against the chart first.

Will the zipper hold up?
The side zip runs on a reinforced track and glides without catching. It's the part most boots get wrong, so we didn't cut corners there.

Are these okay in the rain?
They handle damp sidewalks, puddles, and light rain just fine. They're not rubber rain boots, so skip the deep slush.

How do I keep them looking new?
Wipe them with a damp cloth after a wet walk and let them air dry. Keep them away from direct heat like radiators.

Specifications

  • Size: Foot length 8.9 to 10.6 inches (see size chart)
  • Material: Faux leather upper with imitation leather lining, rubber sole

How to wash

  • Wipe clean with a damp cloth
  • Do not machine wash
  • Air dry away from direct heat
Emma Julia Tania
Emma , Julia , Tania and 250k+ other women are wearing Hollis & Pearl
SHIPPING AND DELIVERY

At Hollis & Pearl, we offer fast, free shipping with UPS on every order.

Once your order has been processed, you'll receive a tracking number so you can follow your package every step of the way and shop with complete peace of mind.

30-DAY MONEY BACK GUARANTEE

At Hollis & Pearl, we stand behind the quality of everything we sell, so every purchase comes with a 30-day money-back guarantee.

If you're not completely satisfied, simply return your item within 30 days of receipt for a full refund, no questions asked.

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★★★★★
Finally, a boutique that understands women like me. Beautiful styles, comfortable fits, and excellent customer service.
Susan M.
Susan M. Jacksonville, FL
★★★★★
Stunning quality, fast shipping, and a perfect fit. Hollis & Pearl is my go-to boutique from now on.
Barbara T.
Barbara T. Wilmington, NC
★★★★☆
The quality exceeded my expectations. Everything feels so comfortable and flattering. I've received compliments every time I wear my pieces from Hollis & Pearl.
Linda W.
Linda W. Savannah, GA
★★★★★
I was hesitant to order online because sizing can be so unpredictable. I'm so glad I did. The fit was exactly as described, and the quality was even better than I expected.
Patricia H.
Patricia H. Charleston, SC
★★★★★
Honestly didn't think I'd love it this much. The material feels luxe and the fit is so flattering. Shipping was fast too!
Judith C.
Judith C. Asheville, NC

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Born in the heart of Charleston.

At Hollis & Pearl, we believe style should feel effortless, elegant, and comfortable. Inspired by the timeless charm of Charleston, we carefully select every piece with quality, versatility, and confidence in mind.

Our grandmother always said, "A woman who dresses with intention, lives with intention." That simple belief continues to inspire everything we do. Every item in our collection is chosen to help women feel beautiful, comfortable, and confident every day.

Thank you for supporting Hollis & Pearl. We're honored to be part of your story.

FREE INSURED SHIPPING WITH UPS
Every order ships free and fully insured via UPS. We want our pieces to arrive safely at your door: fast, reliable and worry-free.
30 DAY MONEY BACK GUARANTEE
Not happy with your order? No problem. We offer a full 30-day return policy, no questions asked. Your satisfaction is our top priority.
100% SECURE PAYMENT
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