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Women’s Annie Leather Riding Boots

STYLE # 50343
Available colors
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), EU42 (US 11)
  • 1.50" heel, 15" shaft, 14" circumference, 1.35 pounds

Women’s Annie Leather Riding Boots


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), EU42 (US 11)
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].

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Reviewed by 19 customers
Displaying reviews 1-10
By Sunny from Colorado Springs, CO
5 5

These riding boots are stunning!

They are slim around calves which is what I was going for to accommodate my slim calves, but they're still a bit baggy on my calves! But it's manageable, I just wear boot cuffs. They are beautiful leather and stunning quality. Definitely stiff and require a break-in period. I love them with leggings or jeans!
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By Linda O. from Emmett,Idaho
4 5

I'm sure I would purchase for myself

Bought these as a gift for my Daughter.
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By krose from Oklahoma
5 5

My husband loves these!

I love the smaller calf diameter. Great leather quality
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By KM from Santa Fe
5 5

Great calf size

I am 5'9 and 135 lbs and almost every boot I try on is HUGE on my calves. The circumference of this boot is flattering for a normal sized/thinner person. The zipper on one side does seem to snag but I think will improve with use.
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By christian from prescott az
4 5

Good Quality boot

Love the look and feel
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By VAD from CA
3 5

nice, but sizing is a little off

I wish these came in 1/2 sizes. I ordered a size 8 and they were too narrow, but the length was ok. After wearing them for 2 days, they did not stretch as the salesperson said they would. So, I exchanged them for a size 9. The 9 was great width wise, but were a bit long, but I wear thick socks. They are comfy and warm, but the 9 does feel a little big. I wish they had an 8 1/2. That size would have been perfect!
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By Alli in SF Bay Area from CA
5 5

Superb !

I wore my new boots for the first time and into the office. They are superb in quality, appearance and comfort, and exceed all my expectations and then some! The most comfortably padded boots ever and highly recommended - not to disappoint. I ordered a size up as the product description suggested - and they fit beautifully. Love them!
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By Happy Consumer from El Paso, Texas
5 5


The boots fit like a glove - can't wait to buy the gloves! Great looking and they're very comfortable. Highly recommend! BTW: When I contacted an Overland Customer Service representative about boot sizes, she was super helpful, very friendly, professional (and spot-on about size).
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By VikkiBT from Fort Worth, Texas
5 5


First time I've ordered boots on line! Went by sizing chart and chat with representative, and the fit is like a glove. Will be showing them off at Christmas party, and I'm so excited. My gift to me! I've already shared the boot and info with close family and friends. Highly recommend!
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By Laura from Oregon
5 5

Like a slipper

Just opened my Christmas gift early and what a pleasant surprise. The most comfortable boots I now own. Quality, luxurious and gorgeous. them.
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Displaying reviews 1-10

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