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Women’s Annie Leather Riding Boots

STYLE # 50343
now $136.50 (was $195)
Available colors
View Size Guide
In Stock - Ships free within 1 business day.
  • Tall leather riding boots
  • Durable leather exterior, side zip entry, elastic gore inserts for a sleeker fit, short stacked heel and treaded rubber sole
  • EU36 (US 6), EU37 (US 6.5), EU38 (US 7-7.5), EU39 (US 8-8.5), EU40 (US 9-9.5), EU41 (US 10)
  • 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.
EU36 (US 6), EU37 (US 6.5), EU38 (US 7-7.5), EU39 (US 8-8.5), EU40 (US 9-9.5), EU41 (US 10)
1.50" heel, 15" shaft, 14" circumference, 1.35 pounds
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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 1-800-683-7526 or by email at [email protected].

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.

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Reviews (top)


Reviewed by 41 customers
Displaying reviews 1-10
By Celeste from Tx
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.
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By Mary from Loveland, Colorado
5 5

So comfy!

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

These boots are perfect!

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.
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By Tochoci from Little Meadows PA
4 5

Not wide calf

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.
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By margo a go go from lake arrowhead ca
5 5

Excellent boot!

Great quality leather! Super comfy!
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By Lisa from Rock Hill, SC
5 5

I love these boots!

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.
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By Rachael from Indianapolis, Indiana
5 5

Finally found the perfect boots!

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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By Dave from New Jersey
5 5

Great boots

I bought for my wife and she loves them. Got a half size up. Perfect fit. High quality product.
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By Connie from Bigfork, Montana
5 5

I am extremely satisfied.

I am always thrilled with the quality and comfort of each item I have purchased. However, I am saddened that Affirm is no longer available. It certainly made it easier for a person in my position.
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By Catalina from Houston
5 5

Sooooooo beautiful

Love love love this boots , so much that I will get this also in black
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Displaying reviews 1-10

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