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Women’s Hailey Wool-Lined Waterproof Leather Boots

STYLE # 58152
now $122.50 (was $245)
Available colors
Size Guide
In Stock - Orders placed within the next 1 hour and 30 minutes ship today
  • 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
  • EU36 (US 5-5.5), EU37 (US 6-6.5), EU38 (US 7-7.5), EU39 (US 8-8.5), EU40 (US 9-9.5), EU41 (US 10-10.5), EU42 (US 11-11.5), EU43 (US 12)
  • 1.50" heel, 11" shaft, 13" circumference, 1.50 pounds

Women’s Hailey Wool-Lined Waterproof Leather Boots


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).
EU36 (US 5-5.5), EU37 (US 6-6.5), EU38 (US 7-7.5), EU39 (US 8-8.5), EU40 (US 9-9.5), EU41 (US 10-10.5), EU42 (US 11-11.5), EU43 (US 12)
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 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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Reviewed by 44 customers
Displaying reviews 1-10
By DD from Stafford Springs, CT
5 5

I would buy this product again.

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.
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By The Mountain girl wannabe from Louisville
5 5

Bring on the Cold Weather

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

every color!

super comfortable
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By Christina from Michigan
5 5

Amazingly soft

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!
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By Suzanne from Florida
5 5


Love them. Very comfortable and warm.
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By Just a girl and her dog from Colorado
5 5

Great boot for serious outdoor activity

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.
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By SophieHiker from Colorado
5 5

Super cute and comfortable after adjustments

I love these boots! (I got them in camel and red, because I have enough pairs of black boots, and the olive color is sold out in my size.) At first they were difficult to get on, with my high instep, and I thought they were too tight, and one of the grommets was pressing on my foot ... So I loosened the laces a LOT, put on a medium-thin sock, put the boots on, zipped them up, and then adjusted the laces. I then wore them around for a few hours. Omigosh, they formed to my feet, just hugging them slightly, and feel wonderful! I love the zipper and laces combo, because as they loosen up I can tighten the laces, as well as accommodate different sock/jeans/leggings thicknesses. They are super cute, with a slightly worn and rugged look. I'll be happily stomping around in the forest as well as wandering around town in them!
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By Wren from Charlottesville
5 5

So cute, so comfy

As much as I hate the cold, I can't wait to wear these! Much cuter on than in pictures. Flatter8ng to your feet and great with skinny jeans or leggings.
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By Rosie from CA
5 5

So cute and comfy!!

I love a pair of comfy boots. These are so comfy and warm. 100% wool lining, waterproof leather, what more can you ask for? Don't forget that they are so dang cute.
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By Kim from Denver, CO
5 5

I love this boot!

Fits so great and super warm and waterproof. Be sure to try on and walk around a bit to ensure proper fit.
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Displaying reviews 1-10

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