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Women's Annie Leather Riding Boots

STYLE # 50343
Available colors

  • Tall leather riding boots
  • Durable leather exterior, side zip entry, elastic gore inserts for a sleeker fit, short stacked heel and treaded rubber sole
  • 1.50" heel, 15" shaft, 14" circumference, 1.35 pounds


Whether you’re saddling up or strolling the town, these tall, cowhide leather boots will navigate the adventure with comfort and good looks. A full-length zip closure eases you in and out, while a 1.5" wide elastic insert along the back length of the shaft adds comfort stretch and textural contrast to this stylish boot. Enjoy all day comfort with a soft leather lining and cushioned leather footbed, along with treaded rubber outsole for a stable step.
1.50" heel, 15" shaft, 14" circumference, 1.35 pounds
Made in:
Product Care:

Overland ships all orders free via standard ground shipping to all 50 states and APO/FPO addresses. For details on expedited shipping or for deliveries to US Protectorates, please refer to the Shipping page.

We want you to be completely satisfied with your Overland purchase. For your convenience, we provide free return shipping for orders within the 50 states, with a prompt exchange or refund process. For more details, visit our Returns & Exchanges page.

Our Customer Service team will be glad to assist with any questions. We are available 7 days a week at (800) 683-7526 or by email at

Overland welcomes international orders. Depending on the order and destination, additional payment requirements may apply. Please refer to the International Orders page for more detailed information.
What is the best way to protect the leather of my Annie leather riding boots? I have a boot balm but I don't want to darken the beautiful leather.
Please follow the link below to the easy details on caring for your leather boots.
By Overland on 11/13/2022


Reviewed by 44 customers
10 of 44 reviews
nancy from chicago
Oct 23, 2023

great quality

5 5
Jessica from Chicago, IL
May 26, 2021


5 5
Most comfortable pair of boots I'm ever purchased. The insole is like walking on a soft cloud. The material isn't stiff like some boots. I've had boots in the past give me blisters, these definitely won't do that. Sizing, because they aren't one or the other, I'm usually a 7 and I could wear a thicker pair of socks if needed. I never leave reviews so that says something.
Vickie from Colorado Springs, CO
May 10, 2021

Best Boots Ever!!!!!!

5 5
I have foot problems and after wearing these every time I take them off. My feet feel wonderful. These are so comfortable I have never experienced before in a boot. Deserves more than 10❤️❤️❤️
Celeste from Tx
Mar 29, 2021


5 5
And if you have thinner legs these are great. I like that these boots are more fitted in the calf area. The stretch in the back of the boot will allows for versatility in leg width but if your legs are thin you don't swim in these.
Mary from Loveland, Colorado
Jan 15, 2021

So comfy!

5 5
I am shocked at how comfortable these are, just never expected that! They are now my favorite boots 😉
A Busy Teacher from Tucson
Jan 13, 2021

These boots are perfect!

5 5
These boots are so wonderful. The shaft is not huge and fits my calf perfectly! I ordered a 6.5 and they were very true to size. I wore them two days in a row and my feet and legs were never sore (which sometimes happens when I get new boots) Honestly, these boots are perfect and I would highly recommend them.
Tochoci from Little Meadows PA
Jan 10, 2021

Not wide calf

4 5
I fell in love with these boots the moment I saw them. I thought the price was kinda steep, but I bought them anyway. They quickly arrived. I opened the well shipped package to find the most awesome black plain leather tall boots. I put one on. It fit my foot perfect. Size 7. Then I tried to zip it up. Even with the elastic on the back of the shaft, it was not going up without breaking the zipper. I was devastated. I put them back in the box and tried again in the morning. Same thing. Sadly I packed them back up and shipped them back. These would have been perfect for work and riding my motorcycle. I just needed a little extra in the calf.
margo a go go from lake arrowhead ca
Dec 23, 2020

Excellent boot!

5 5
Great quality leather! Super comfy!
Lisa from Rock Hill, SC
Dec 10, 2020

I love these boots!

5 5
I have been wearing them to work, and they are the most comfortable pair of boots that I've ever owned. I have worn them with skinny jeans and boot cut jeans, and they look great with both. The quality is superb. I purchased the size 9, and the fit is perfect, true to size.
Rachael from Indianapolis, Indiana
Dec 2, 2020

Finally found the perfect boots!

5 5
I've only had them about a week, but they are exactly what I was looking for! Comfy but should get even comfier with each wear. Fits snuggly around my calf but has some stretchy material on the back so they're not too tight. Great color, great leather. I'm a size 8 with slightly wide feet, and I ordered a EU39, and they're perfect. Can be dressed up or down. I'm very happy!
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Our Values

A lot has changed since our humble beginnings in Taos, NM, over 50 years ago—but the core values of our family business have always remained the same. Now, as then, we're dedicated to bringing you heritage-quality products expertly crafted from the world's finest natural materials.
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