Skip to Main Content Skip to Footer

Women’s Ann Shearling-Lined Waterproof Leather Boots

STYLE # 58506
Available colors

  • Waterproof full-grain leather and suede boots with shearling lining
  • Shearling-lined shaft and wool-lined footbed, full inside zipper, thermo rubber outsole, 3mm memory latex footbed
  • 1.50" heel, 9" shaft, 12" circumference, 1.32 pounds


Looking for trusty winter boots with timeless style? Slide into the Ann waterproof leather boots, featuring a rugged waxed full-grain leather vamp and soft waterproof suede shaft. Covering the supportive memory-latex footbed is breathable Merino wool, while the shaft is lined in plush, insulating shearling sheepskin. Thermo rubber outsoles provide traction on slippery paths, while an inner zipper offers easy on/off.

This boot is crafted with an intentionally unlined heel, which prevents socks from catching and heels from rubbing, enabling a more secure and comfortable fit.

1.50" heel, 9" shaft, 12" circumference, 1.32 pounds
Made in:

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.
Are these boots lightweight? I have found that I can't wear Dr Martins due to the weight. Love these boots! Thanks ☺️
Hello! The Ann Shearling-Lined Waterproof Leather boots weigh approximately 1.32lbs each. Please feel free to contact our friendly customer service team at 800-683-7526 or for any further questions. Thank you!
By Overland on 12/20/2023
Can you say if they run small or large? I wear a size 6 1/2 or 37.
These run true to size. You may want to take in the thick shearling lining to account when thinking about fit.
By Overland on 11/27/2023
What about arch support?
Thank you for reaching out. While it does not have a high arch support it does offer this supportive memory-latex footbed is breathable Merino wool, while the shaft is lined in plush, insulating shearling sheepskin. Please reach out to us at 1-800-683-7526 or for further assistance.
By Overland on 10/20/2023


Reviewed by 23 customers
10 of 23 reviews
Karol from Madison, WI
Feb 26, 2024

A Company That Exceeds

5 5
I was looking for a high quality boot that was comfortable and didn't require I take out a mortgage. Overland boots are amazing! Service was superb, I received my boots within 2 days of ordering. I will definitely be back!
Carmen from Alameda CA
Jan 25, 2024

Love them boots

5 5
The are very super comfortable boots, love the color is great, love my boots I've gotten lots of compliments.
Neets from Santa Monica CA
Jan 25, 2024


5 5
Love my boots. So comfy
Evelyn from Helen, GA
Jan 24, 2024

Talk about QUALITY!

5 5
The craftsmanship is impeccable.. ordered a second pair as these are a little big for me. I usually wear 38. Other than that, I can't wait to get them! Free returns...what a bonus! Love Overland!
Renee from Moab, UT
Jan 22, 2024

Beautiful, comfortable, excellent quality!

5 5
Love the boots! Now I want more!
Jennifer Hammerstrom from Tracy, Ca
Jan 21, 2024

Excellent product

5 5
So comfortable and live the way they look and feel
Sunvalleysusanna from Hailey, Idaho
Jan 21, 2024

Love these!!!

5 5
These are even more beautiful in person, and fit perfectly, like a glove, true to size. I am an 8 and ordered size 39. I ordered the grey and they are the perfect color, not brown, not black, and I particularly like the solid dark sole without the white stripe in it. I had planned to order them after Christmas and was so sad to discover they were out in my size! I kept looking and immediately ordered when they were back in stock, perhaps from a return... I am so happy, these are beyond amazing🩷
EWokfe from Oregon
Jan 17, 2024

Super cute but sent wrong size

3 5
I was really excited for these. They sent me a size 7 in a size 9 box I returned them. I'm gonna try the mustangs, but I might end up getting these instead in the right size.
Bonnie from CA
Jan 15, 2024

Lookin' Good!

5 5
Great looking and comfortable boots! Exceeded my expectations! Highly recommend!
Melody from Little Rock AR
Jan 15, 2024

beautiful quality

4 5
This boot is just as pictured. the leather is beautiful and the shearling lining keeps my feet very warm. wore them today in the snow and loved them. they are not heavy like some snow boots. They do slip a little in the heel, but am hoping a thicker pair of socks will correct that!

Image Thumbnail

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.
This is size content
This is color content

Screen reader users call 1-800-683-7526 to chat with a representative.