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About Madewell

The Winston Boot
full size
The Winston Boot
The Winston Boot
Product Details
You'll be hooked the moment you slip them on: In the richest Italian leather with a subtle worn-in finish, they're as perfect with dresses as they are with skinny jeans. And for such stylish works of art, the price is molto bene. Please note: When you select your size below, "H" equals a half size.
  • Hits at ankle.
  • Inside zip.
  • Leather upper and lining.
  • 3 3/4" shaft height (based off size 7).
  • 9 3/4" shaft circumference (based off size 7).
  • 2 1/4" stacked heel.
  • Man-made sole.
  • Import.
Free shipping exclusively for Madewell Insiders
*For complete details, see our Shipping Policy.

The Winston Boot

The Winston Boot is rated 4.8 out of 5 by 70.
Rated 5 out of 5 by from perfect staple for my wardrobe! These boots are made of beautiful leather and I'm so glad I invested in them...timeless and classic, they will be a staple in my wardrobe for years to come. I usually wear a size 5.5-6. I was once told by a sales rep that you should always order half a size up for boots when I bought my first cowboy boots and I have always stuck to that rule. I ordered a size 6.5 and they are perfect!
Date published: 2013-09-12
Rated 5 out of 5 by from Amazing color and well-made I took advantage of the recent 40% off and ordered my normal size US 7.5 in Plum. I was worried about the color would be too red too bright. When I opened the box, the color is amazing, it is like dark brown with a touch of plum and a bit of red shade. The leather is thick and in high quality, and craftsmanship is great which make them so sturdy and solid. 2" walkable heel, side zip makes it easy to go on and off. The opening is not wide at all, which wraps around the top of my ankle comfortably and nicely. They are very versatile and go well with skirt, dress, jeans and etc. They do need a break in time though due to the stiff of leather.
Date published: 2013-10-27
Rated 5 out of 5 by from Versatile black bootie! These black booties are incredibly versatile - great with jeans and a workshirt during the day, yet perfect with a dress and tights in the evening. They rubbed at the outer ankle for the first few wears, but are fine now that they are broken in. Comfortable and walkable - and this means a lot coming from someone who only wears flats or sneakers! I typically wear an 8.5 (rarely an 8) and have an average foot width; the 8.5 was true to size.
Date published: 2013-10-23
Rated 5 out of 5 by from Looks awesome Love this shoe! Great with skirts or skinny jeans. Would definitely recommend.
Date published: 2013-10-21
Rated 5 out of 5 by from Very high quality! So impressed I adore these boots - I have worn these every day with jeans, dress pants, and dresses - they are very versatile. The quality of the leather is very evident, and they just look stunning. They are very comfortable, and after about a week of solid wear, I can feel that they are molding to my feet. One thing to mention, which I thought was a plus, but others might not, is that the ankle (at the top of the boot) is very loose. This makes them very comfortable as they are not constricting the ankle and lower calf, but just a note to others that they fit this way.
Date published: 2013-10-19
Rated 5 out of 5 by from Perfect autumn boot I've been wearing my boots for a few weeks now and could not be more pleased. The size is perfect; I am a 6 1/2 (narrow) and often have trouble finding well sized shoes. Also very comfortable - perfect for the end of summer and through the fall!
Date published: 2013-10-10
Rated 5 out of 5 by from Very Comfortable I was talking about not being able to find quality footwear when a manager from a different store told me how pleased she was with the shoes she purchases from Madewell. I'm always on the prowl for quality footwear regardless of price. I've tried almost every high end shoe designer you can think of, and without fail after a few wears the shoe begins to hurt or leave blisters, so I decided to give Madewell a try and I am not disappointed. I purchased these boots in burgandy, they're the most comfortable pair of booties I've bought on line in a long time, especially for the price. The leather is very soft, the footbed cushioned and the heel height perfect. The only con, is the color, they're a light burgandy, but I can live with that. You can dress these boots up or down. If you're looking for a quality leather boot at an affordable price, I'd recommend these boots, I don't think you'll be disappointed. They do run a tad big, but it wasn't enough to order a smaller size.
Date published: 2013-09-23
Rated 5 out of 5 by from Cute and Versatile These are well made for the price and absolutely true to size. Perfect height for pants or dresses/skirts. I wish I had jumped on the "antique brick" color while it was available, because I would definitely buy a second pair. Made in Romania too, not China as I assumed would probably be the case.
Date published: 2013-09-06
Rated 5 out of 5 by from Great fall boot! Very good looking boots. A little stiff but they should loosen up with wear. A fall must have!
Date published: 2013-08-22
Rated 5 out of 5 by from Classic and Comfortable LOVE this bootie! I wanted it in brown but only black and brick were available. I went with the brick and it's a great color, works as a neutral just like brown and goes with most everything. A little stiff first wear but they break in easily. I'm usually a 7.5 or 8 and I'm glad I got the 8, fits perfectly. Zipper on the inside makes putting on/taking off easy.
Date published: 2013-08-17
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