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Women’s Hailey Wool-Lined Waterproof Leather Boots

STYLE # 58152
now $122.50 (was $245)
COLOR: RED/SANGRIA
Available colors
Size Guide
In Stock - Ships free within 1 business day.
  • 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), EU44 (US 13)
  • 1.50" heel, 11" shaft, 13" circumference, 1.50 pounds

Women’s Hailey Wool-Lined Waterproof Leather Boots

Details

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).
Sizes:
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), EU44 (US 13)
Specs:
1.50" heel, 11" shaft, 13" circumference, 1.50 pounds
Made in:
Portugal
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].

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Reviews

Reviewed by 36 customers
Displaying reviews 1-36
By Rosie from CA
VERIFIED REVIEWER
5 5
 

So cute and comfy!!

3/24/2020
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
VERIFIED REVIEWER
5 5
 

I love this boot!

3/8/2020
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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By PNWwaterproof from Seattle, WA
VERIFIED REVIEWER
5 5
 

Accentuated curves on boots? YES

2/19/2020
Ever love a boot so much you get it in multiple colors? This is that boot, i was skeptical for a $300 boot that looked so cute online. Alas it is just that cute in person :) Just like that another color in my cart and on my feet. Living in the PNW warm and waterproof are NEEDED, but so is fashion. Thanks for the lovely style
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By smylins from Houston, TX
VERIFIED REVIEWER
2 5
 

Looks Great BUT!

2/14/2020
The Overland Hailey boots look great from the outside, but no so much on the inside. The boots are constructed from mixed materials including leather, suede and wool with an appealing color palette. The shoe laces were soft and flexible, though I would rather have tighter weave for durability. The outsole is thick and has superb traction. On the inside, the wool lining and insole needs improvement. The wool lining is poor quality and detaches very easily. The insole doesn't have cushion or a soft footbed. I highly recommend a shoe insert for comfort and to reduce ground impact on the feet. Overall, the exterior style was executed well, but lacks the high quality of a wool lining and soft footbed.
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By 15917 from NE
VERIFIED REVIEWER
5 5
 

I love theses boots!

2/12/2020
I routinely am outside in the inclement weather (I have a awesome second job walking dogs) and as the Midwest is constantly labile in her temperature, I wanted a comfortable, waterproof, WARM (aka insulated) boot that I could use during these times. Primarily, I bought a pair of boots from a different retailer, but decided they were a bit too cheaply made for my uses. Enter this pair of Hailey boots from Overland. Not only were they only $25 more than try first try (I was stoked that the Hailey's were on sale), but the insulation was true Merino wool, the leather was beautiful and WATERPROOF, and they are so comfortable! It was a no brained for me. My only caveat with the Hailey's is that the wool insulation lining the inner portion of the boot sheds a bit. I read the reviews on multiple Overland items, and there is evidence enough for me that Overland honors its warranty and has trustworthy customer service...in the case that I do feel that the insulating wool lining is becoming bare. Anyway, I am so happy I bought these boots!!
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By Rachel from Atlanta, GA
VERIFIED REVIEWER
5 5
 

Love my new boots!!

2/9/2020
Side zipper is amazing - very warm!!
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By Kat from Riverton, WY
VERIFIED REVIEWER
5 5
 

Best boots ever!

2/8/2020
Stylish and comfy Long-lasting Wish i had gotten the sheepskin insoles to put in the boots
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By Diane E from Summit County
VERIFIED REVIEWER
2 5
 

I will not buy this product again.

2/6/2020
I really like the color. I own a red and green pair from previous years. But this year the boots are not made by Bos & Co and the quality isn't the same. I will be returning them to the Breckenridge store. I'm really disappointed that I can't add a black pair to my collection. They hurt my feet. For 4 yrs I have recommend this style to friends. Hopefully you will return to quality boots next year.
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By amber from AK
VERIFIED REVIEWER
5 5
 

I love these boots

2/6/2020
These boots are not as black as they appear in the photo (more subdued? matte?) but are so great. I love the way they fit, they are tight enough around my scrawny ankles, have comfy wool lining, and so far, seem pretty comfortable (I expect as they get worn in, they will be more comfortable, but as leather they are a bit stiff yet) They make me feel a little punk rock and are pretty adorable.
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By JW from Pennsylvania
VERIFIED REVIEWER
5 5
 

Great purchase!

2/3/2020
Comfortable, cute and waterproof.
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By CeeLine from Ohio
4 5
 

Had to return

1/28/2020
Beautiful boot and well made. I had to return because the leather is too stiff for me and the foot bed does not have the cushion that I need for my feet, even with added insoles. Sorry I couldn't keep them, they are so very cute on!
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By Alicia the skiier from New York
VERIFIED REVIEWER
5 5
 

I would absolutely buy Overland Boots again

1/27/2020
Warm wool inside, easy to get on/off with zipper. Comfortable to walk in and love the style.
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By LoveOverland from Tacoma, WA
5 5
 

You can't go wrong with these

1/25/2020
This is my 2nd pair, other pair is red. I live in the pacific northwest....it's wet. These keep my feet warm, and dry. If the temperatures are lower, I wear smart wool socks. I'm a truck driver and wear them to work, the sole is sturdy, yet flexible, and fairly non-slip....super comfortable boots. Always, always get compliments. I pretty much wear them 24-7 in the rainy season so that's roughly 9 or 10 months out of the year. They have worn well and when I had an issue with a zipper after almost a year the company exchanged them with no problem😊
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By Whit from Ohio
VERIFIED REVIEWER
5 5
 

Worth every penny! 5 Star!

1/18/2020
Love these boots! Casual and fun! I bought them in Colorado and live in the Midwest, everyone comments on their quality and beauty which I can 100% confirm. The boots are also very comfortable.
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By Amanda from Memphis, TN
VERIFIED REVIEWER
5 5
 

So cute AND comfortable

1/16/2020
I wear my boots several times a week. They are so comfortable and warm. I receive compliments on them every where I go
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By Cathy from Chicago
VERIFIED REVIEWER
5 5
 

Cute, comfy, & warm

1/15/2020
Great boots! So warm, completely lined. Zipper closure so you don't have to untie them. Nice detail, & great quality. So glad I caught them on sale!!!
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By Sandra from Reno, Nevada
5 5
 

Overland quality!

1/14/2020
Love my new boots!! I will wear them for many years! Thanks Overland..again!
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By Hum from Milton, ON
VERIFIED REVIEWER
5 5
 

Excellent Boot

1/11/2020
I love this boot. It fits my foot like a glove. Great tread for gripping the ground. Heel is just high enough to keep my high arches happy! I can wear with formal or casual clothing. I also love the textures - leather, suede and cloth. Great colours to go with anything😊
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By Emily from Santa Fe, NM
VERIFIED REVIEWER
5 5
 

I love these boots!

1/10/2020
They are a little tight and hard to get on originally, but once they break in they are amazing. I haven't tested the "waterproof" feature, but my feet are nice and warm.
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By Annie from Wallingford, vermont
VERIFIED REVIEWER
5 5
 

...I love the boots!!!!

1/8/2020
...wearing them every day, I live in Vermont and they are perfect!!!!
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By KKsmallFry from Dallas, TX
VERIFIED REVIEWER
5 5
 

Beautiful & comfortable

1/5/2020
I got the camel color & love it!!! I normally wear 6.5 so I got size 7. It fits so well & I can even wear thick socks with it. I was walking in the snow & some icy area in CO without slipping & sliding. It definitely has good traction. It is also very comfortable! I'll be bringing it to go to Finland with me in March.
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By Sarag from MO
VERIFIED REVIEWER
5 5
 

Quality, style AND function -trifecta !!!

1/4/2020
Super picky shopper, quality exceeded expectations ... These will last for years! This seller has the EU sizes translated correctly, not everyone does. LOVE!
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By Sandy from Boerne tx
VERIFIED REVIEWER
4 5
 

Just as beautiful as I expected

1/3/2020
Lining not to much, beautiful leather and plaid material
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By Blessed In So. Oregon from Eagle Point Oregon
VERIFIED REVIEWER
5 5
 

OMGosh!!! I'm In Love!

12/31/2019
These boots are amazing!! My hands and feet are always cold in the winter. My amazing husband knocked my socks off and bought me Overland's Hailey AND two additional styles of their lined, waterproof boots for Christmas. All three are beautiful, appear to be extremely well made, comfortable (unlike every other "warm" boot I've ever tried on) and truly keep my toes and feet warm. I anticipate getting many, years of wear from these boots. I'm struggling deciding which is my favorite! Now I just need to find a product that does as good a job for my cold hands.
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By BoomerDB from Rockville MD
VERIFIED REVIEWER
3 5
 

Does not fit true to size

12/25/2019
Great looking boot and looks like it's made extremely well but way too tight on my wife's feet. Unfortunately a Christmas present that has to be returned for next size up. I'm sure once we get the boots fitting correctly we will be fully satisfied, just not good timing to not fit Christmas morning.
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By Guissy from Houston Texas
VERIFIED REVIEWER
5 5
 

OMG the boots!

12/9/2019
These boots are something else! They are super comfortable and more beautiful in person that in the website. I got them in red and absolutely gorgeous. I had to release the straps as it was a little tight. Next ones I would get it a big size as because all internal coating it could be smaller that regular size. I really loved it.
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By Laurie B. from Michigan
VERIFIED REVIEWER
5 5
 

Stylish, warm boots!

12/5/2019
No breaking in, very comfortable right out of the box! They are true to size, keep my feet toasty warm and oh so stylish!
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By Sunshine in Colorado from Castle Pines, CO
VERIFIED REVIEWER
5 5
 

All Weather Function, Lovely Form

11/24/2019
These boots are cozy and comfortable. How lovely it is to confidently (sure footing) stride through the outdoors (snow, slush, fairground mush) into multiple scenarios without needing to change footwear! I've the loden color which is a wonderful neutral.
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By Kim from Rochelle, IL
VERIFIED REVIEWER
5 5
 

Absolutely Love Them

11/11/2019
I have only worn them twice as the weather is such that I need them. I have had multiple compliments on them due to the style. They keep keep my feet warm and dry and they are extremely comfortable! Love them!
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By Angel from Chicago, IL
VERIFIED REVIEWER
5 5
 

Beautiful and comfortable

11/7/2019
I bought the red pair and as someone else said, it looks better in person. I don't usually wear colored shoes because it stands out for better or for worse, but this color and design is just striking and works both with my muted outfits (black, brown, cream) or jewel-toned outfits. The boots add a nice touch to my long coat and skinny jeans. I usually wear size 6.5-7.5 (it's a huge jump but it depends on the shoe brand) and got the EU 37 (6-6.5). It was snug but after breaking it in a bit, fits my feet perfectly with wool socks. I like it so much that I may buy the Olive one next.
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By Lynn from Monroe, WA
5 5
 

I would but these boots again.

11/7/2019
I live near Seattle where it rains and rains and rains so I love that these boots are waterproof. They are comfortable and warm also! I am so happy I bought them.
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By Jean B from Wisconsin
5 5
 

Really great boot!

11/4/2019
Stylish and comfortable.
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By Jai from Denver
VERIFIED REVIEWER
5 5
 

Going to order same boot in two more colors!

10/30/2019
I was a little concerned about the tongue in the boot when I tried it on in the store, where is was sewn to the toe was noticeable on the top of my foot. I decided to buy them and give them a try and I was so incredibly pleased with the comfort and style today I decided I was going to buy them in two more colors! Super comfortable, warm and tons of compliments! Definitely a must.
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By Debbie from Farmington, Utah
VERIFIED REVIEWER
5 5
 

Excellent boots

10/28/2019
Love the feel, fit and style of these boots #sweepstakes
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By Tara from Seattle, WA
VERIFIED REVIEWER
5 5
 

Warm, comfortable, and true to picture

10/24/2019
My size is an 8.5, so I ordered the 39. They fit perfectly with room to wear wool socks. I love them and plan to order more from overland in the future because their quality and costumer service is the best I've encountered. #sweepstakes
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By Coat and Shoe Fanatic from Breckenridge Colorado
VERIFIED REVIEWER
5 5
 

I am glad I bought this boot.

10/3/2019
The boot is comfortable and warm. It looks great and stylish. Looks better on than in the picture. I had trouble picking a color. They all looked great. I am hoping the lining inside doesn't leave crevices on the bottom of the foot. The zipper helps not having to tie the shoe every time. Yes very pleased.
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Displaying reviews 1-36

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