Skip to Main Content Skip to Footer

Women's Hailey Wool-Lined Waterproof Leather Boots

STYLE # 58152
Available colors

  • Lace-up waterproof leather boots with wool lining
  • A delightful mix of patterned wool, soft suede, and sturdy leather, full side zips for easy on and off, warm wool lining, lug sole with 1.5” heel
  • 1.50" heel, 11" shaft, 13" circumference, 1.50 pounds


Outdoors or in, our Hailey lace-up boots keep you weatherproof and styled. Wool lining means feet are cozy and dry, while a fusion of leather and suede with plaid trim adds the urban touch to a rugged winter boot.
  • Fusion design of leather and suede with fashion plaid trim
  • Waterproof boots with full inside zipper for easy on
  • Merino Wool lining keeps feet warm, dry, and comfortable
  • Non-slip traction sole + heel
  • Cold comfort rated by the manufacturer to -13°F (-25 C).
1.50" heel, 11" shaft, 13" circumference, 1.50 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.


Have a question about this product?


Reviewed by 48 customers
10 of 48 reviews
Danielle from Montana, USA
Nov 16, 2020

Truly waterproof/wool liner cozy

5 5
I have both the red pair and the black pair. Best boots I've ever owned. They are sturdy, 100% waterproof, and so cozy. My state received record early snowfall in October, and I used these boots to shovel. They were/are perfect. I definitely will buy them again whenever these wear out....which does not look to be in the near future.
Robin from Soso, MS
Sep 27, 2020

Love love the quality of these boots

5 5
I saw these boots last year when we went to Wyoming & I fell in love w/them. So this year they had one pair left. They were my size. Can't wait for it to get cold enough to wear them!
Rachel from Littleton, CO
Sep 24, 2020

Cozy Warm Boots

5 5
I had been looking for a new pair of boots for the upcoming Fall and winter here in Colorado. I wanted something that will keep my feet warm, is easy to take on and off, and is fashionable. Another pair of boots led me to the Overland site, which ultimately didn't quite fit what I was looking for, but helped lead me to the Hailey boot. I am so pleased that I found this boot as it is exactly what I was seeking. I cannot wait for our weather to cool, so I can start wearing them.
MomBear from Chicago, Il
Sep 23, 2020

Love These Boots

5 5
Have only had the opportunity to wear these once, but they were super comfortable. Can't wait to wear these this winter.
DD from Stafford Springs, CT
Sep 22, 2020

I would buy this product again.

5 5
Boot was a bit roomy as I bought a size larger than the normal 10 1/2 wide, instead purchased the 12 because you were sold out of size 11. It was the perfect color and the inside was warm and soft to the touch. I can fill the extra room with thick soft wool knee highs and I am certain they will keep my feet warm. The only concern I had was I read somewhere in Overland articles that Leather CANNOT be make TOTALLY WATERPROOF yet I purchased these as WATERPROOF LEATHER BOOTS. I am a Diabetic and my feet cannot get wet in the Winter Time. I hope these really pretty boots live up to the standards they were sold to me as. They were super comfy and I had enough room to add sheep liner in the foot bed. I like these boots a lot and am glad I bought them.
The Mountain girl wannabe from Louisville
Sep 16, 2020

Bring on the Cold Weather

5 5
These boots are so comfortable,stylish, and warm. Looking forward to cold weather so I can wear them.
Ly from taos nm
Sep 14, 2020

every color!

5 5
super comfortable
Christina from Michigan
Sep 11, 2020

Amazingly soft

5 5
Very soft leather, feels great to the touch, excellent stitching and very comfortable to wear. The wool lining is the best part, soft, breathable just not too warm, my feet tend to overheat in the synthetic lining. Love it!
Suzanne from Florida
Sep 5, 2020


5 5
Love them. Very comfortable and warm.
Just a girl and her dog from Colorado
Sep 4, 2020

Great boot for serious outdoor activity

5 5
Needed a tough boot after purchasing large land and cabin. It has tough terrain and changing weather. It was important that I could just slip my boots on and go. This boot allowed for that since it has lace adjustment and then a full length zipper to easily slip on. It is a hardy but also soft and comfortable boot. The soles grip well in the dirt and tundra.

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.