Women’s Riding Boots Only $19.99 (Regularly $50) | Macy’s Black Friday Special Sale

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More Macy's

 Style & Co Madixe Riding Boots on display in Macy's store

Macy’s is the place to shop for amazing deals on shoes, jackets, kitchen items and more!

Through November 30th or while supplies last, head over to Macy’s and score some amazing deals on select Women’s Boots with prices starting at just $19.99 (regularly $49.99+).

Be sure to take a little time to browse around as you’ll spot a wide variety of styles on sale.

Here are just a few of the great deals on boots…

Style & Co. Madixe Riding Boots
Only $19.99 (regularly $49.99)

Available in black or cognac, these round-toe riding boots feature a full side zipper, crisscrossing ankle strap and buckle detail.


American Rag Cadee Ankle Booties
Only $19.99 (regularly $49.99)

Available in multiple colors, these Cadee round-toe booties feature a curving notch on one side balanced by a quick side zipper on the other.


Style & Co Kelimae Wide-Calf Scrunched Boots
Only $19.99 (regularly $49.99)

Available in multiple colors, these casual slouching wide-calf riding boots offer a 1″ heel, round-toe and a half side zipper closure.


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  • Shipping & Terms

    Macy's

    Shipping is free on orders of $25+ for Macy's Star Rewards Members (free to join), otherwise, it's free on orders of $49+. Score free shipping on all orders when you use your Macy's Credit Card with Gold or Platinum status.

Join The Discussion

Comments 19

  1. Janarobyn

    Thank you! I appreciate finally seeing a style that comes in wide! They are so hard to find for a decent price.

    • Collin (Mrs. Hip)

      Oh great! You’re so welcome! Happy you could find the size and fit you needed!

    • Loudflower

      I received mine.

  2. brindhaG

    Got the booties in grey! Happy to find wide width with decent prices. Thanks!

    • Jennifer (Hip Sidekick)

      You are welcome, brindhaG!

  3. SaraJC

    Awesome! I just ordered some boots! I added another $5 purchase to get free shipping! 🙂 thanks so much for posting!

    • Jennifer (Hip Sidekick)

      No problem, SaraJC! Enjoy your new boots!

  4. Erica

    Off topic. Did anybody receive the coupons and cash card from the last Costco membership promo at Groupon?

    • Lisa

      I did! I even received them sooner than they predicted.

      • Erica

        Thank you, Lisa! I think my sister put mine in the trash. 🙁 She thought it was some of those credit cards offers:

  5. Jennifer

    What is the return policy? I don’t live within 100 miles of a store.

    • Jennifer (Hip Sidekick)

      Great question, Jennifer! You can read about the return policy here!

  6. mparanz

    I feel like these boots are always this price last year after Black Friday they were even cheaper !

    • Leslie

      Yes, they’re almost always $19.99 on special sale for the holidays about every other week but they do get cheaper if not sold out for Black Friday. We had so many Cadee, Kelimae, and Madixe leftover in January that our inventory was inaccurate. I used to work at Macy’s women’s shoes so I got the American Rag Cadee for $9.96 in like March that turned out to be less than $8 with my employee discount.

  7. Kiki

    Does anyone have any recommendations for tall black riding boots that fit their SKINNY calves? I’ve been looking for a long time for some that aren’t wide at the top, but they always seem to be too loose over the calves I really would like to find something more fitted. Does anyone have any they love? TIA!

    • Mindy

      I got a pair of Madixie last year and I love it. My naughty husky puppy chewed them though, so I bought another pair from Amazon last summer since Macy was out of size 6. They fit my calves just right without huge gap like other brand. Try out at the store if you have one close by.

      • Kiki

        Thanks for the suggestion!

  8. Lali

    They are having an additional $10 off sales and clearance items at checkout right now. It offers it at the side of the page!

    • Jennifer (Hip Sidekick)

      Thanks, Lali!

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