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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 Love the colour! I have been looking for a while for a pair of plum booties. I have a plum leather coat so when I saw these booties available in a plum colour, I immediately bought them. I am usually a 6 for flat shoes and a 6 1/2 for heeled shoes. I purchased the 6 1/2 size, and these booties are very comfortable. I tried them for half an hour since it still is hot outside to wear them.
Date published: 2013-07-30
Rated 5 out of 5 by from Great Boot! I got these in black and love them. I find they run true to size. I don't usually wear heels so I was pleased that these are comfortable and very walkable. A bit pricey but a great boot!
Date published: 2013-06-20
Rated 5 out of 5 by from true to size I'm wear size 6.5-7 in almost all shoes, so when I saw these boots on sale and the only size left was a 7.5, I went ahead and took a leap of faith (after reading the reviews) and decided I could just return them if they were too large. Turns out they're definitely true to size. The 7.5 were just slightly too long for my feet but the boots are so beautiful and the brown color in my size is sold out online and in all stores near me that I decided to keep them. I would recommend wearing socks that go higher than your ankle, as the leather is pretty stiff at the top of the boot and will rub. My pair also do not have a "subtle worn-in finish" which is just fine with me, but just in case you care, they look pristine out of the box.
Date published: 2013-05-25
Rated 5 out of 5 by from Love these boots! I've been looking for a nice pair of booties for a while and found the perfect pair in The Zipcode Boot! The are true to size, well made and very comfortable. I wore them on a trip to San Francisco and were comfy to wear all day long walking around town. They are also very versatile. I wore them dressed up and down. Can't go wrong with these boots. Don't think about, just pull the trigger and buy them. You won't regret it!
Date published: 2013-05-24
Rated 5 out of 5 by from LOVE this boot!!! I have been searching for a boot like this for some time, well made, versatile, and just the right heel height. Have terrible feet (bunions), but I can walk in these for hours with no pain. I found them to be true to size. I will definitely order a pair in another color.
Date published: 2013-05-19
Rated 5 out of 5 by from Classic-good quality ankle boots The zipcode boots are what I was looking for: cute looking, good quality, comfortable... I love them. I usually wear 6.5, but for boots go up to 7, and the boots fit perfectly.I got mine in black, the color is true black, not too shinny or matte. What I like the most is the overall quality of the boots. I have wear them mostly with skinny jeans, but I am sure will look great with skirts/dresses.
Date published: 2013-05-11
Rated 5 out of 5 by from Cute Booties These boots are super cute and I've received multiple compliments on them from men and women of different generations. My feet are in terrible condition (had to see a podiatrist), so this shoe is great because it's not too high and the heal is supportive. At regular price, I don't think the shoe is a good deal; but I purchased my booties on sale, which made them a great value. I recommend wearing these with ankle socks (or tights) because the shoes tend to rub against the ankles. Boots are true to size.
Date published: 2013-05-09
Rated 5 out of 5 by from Overall definitely worth it! These boots are great! I sized up as per the recommendation of some other reviewers, and that definitely was the right choice for me. I am usually a size 10-10.5 and the size 11 was perfect. In the description of the boot it says it has a subtly worn-in finish, which my pair definitely was not. Maybe it's just more noticeable on the brown leather version? They are quite shiny and smooth out of box, but I am totally okay with this. The only problem I have with them (but it's not a big problem enough problem to want to return them), is I find the heel area of the boot quite loose. So toe to heel the boot fits great, but there is quite a bit of room for heel to move around side to side. I do have quite narrow feet though, so maybe only take heed if you do as well.
Date published: 2013-04-25
Rated 5 out of 5 by from Leather molds right to your feet! I typically buy a 9.5 but I had tried on a different bootie at the store that was a 9 and so I took a leap of faith and ordered a 9 in these booties. After one wear they fit like a glove. Feels like your feet are covered in paraffin wax!
Date published: 2013-04-23
Rated 5 out of 5 by from Beautiful Quality - very versatile. These were a little more reddish than they appear in the picture, but I imagine they'll mellow out a bit with wear. I've gotten a ton of compliments on these boots, they fit well with skinny jeans or skirts, and they're comfortable enough to wear all day. Very high quality and well-made boot, I'm sure I'll be wearing these for years to come. I ordered a 9 in these boots, and I normally wear an 8.5 for everything but a running shoe. The 9 fits perfectly with a light sock.
Date published: 2013-04-20
Rated 5 out of 5 by from Hooked on these boots! although they were back ordered, they were completely worth the wait! they are comfortable and match every outfit! wearing these everyday!
Date published: 2013-04-11
Rated 5 out of 5 by from Adorable, sexy boot These boots are super flattering -- I love the look of them. They are also the most comfortable heels I own. I have been able to walk all over the city without the slightest discomfort. I will undoubtedly have to get them resoled soon though, considering that the heel is already wearing down a bit. I expect I'll be wearing them season after season.
Date published: 2013-03-27
Rated 5 out of 5 by from Must-have boot! I just got my boots about a week ago, and they've already become my favorite pair. They go with everything, they're cute, AND they're comfortable - the trifecta of perfect shoe qualities!
Date published: 2013-03-27
Rated 5 out of 5 by from this is really chic! i got this shoes through the online cause my size is 5. My overall rating is EXcellent. really comfort and look great! :))
Date published: 2013-03-26
Rated 5 out of 5 by from Beautiful Boots These boots are gorgeous. Very comfortable and stylish. I sized up to a 9 because I'm an international buyer and feared they would run small but this was not the case. I should have stuck with my usual 8.5. Highly recommended.
Date published: 2013-03-26
Rated 5 out of 5 by from Perfect boots I totally fall in love with these boots! Anything goes well with them.
Date published: 2013-03-26
Rated 5 out of 5 by from Great, comfy boots! I love these boots and was rapt to get them on sale! They look great and are super comfy... I find them to be true too size too. Definitely recommend!
Date published: 2013-03-26
Rated 5 out of 5 by from Great booties, lots of compliments I got these booties and I love them. The color is gorgeous and they are actually really comfy to wear standing at a bar all night. One of them rubbed a little bit on my ankle at first but after a couple wears they don't rub anymore. Highly recommend, I get complimented every time I wear them!
Date published: 2013-03-25
Rated 5 out of 5 by from Perfect Bootie! This boot is fantastic for jeans and dresses and is a perfect color. The leather is really beautiful in person, and they are constructed to last... So refreshing!
Date published: 2013-03-23
Rated 5 out of 5 by from Perfect boot! This boot looks great with everything! I wear a 8 1/2 and I always worry about a boot making my feet look too big, but this one did not. This boot is cute and classy. The heel is the perfect heighth for casual wear and work. It rubs at the ankle just a little bit, but that can be fixed with an ankle sock. Overall this is a great boot!
Date published: 2013-03-20
Rated 5 out of 5 by from Stylish and comfortable A great purchase. These boots look great, are extremely comfortable and are the perfect height for skinny jeans. Found look-a-like boots at another store but decided to keep these as they were far superior in quality.
Date published: 2013-03-12
Rated 5 out of 5 by from Perfect I wear these all the time, and the have held up really well! So comfortable too!
Date published: 2013-03-11
Rated 5 out of 5 by from love it love, love these boots! they are simple and understated, but i was looking for something without any bells and whistles. extremely comfortable, and seem to require almost no breaking in. i do think they run small, though. i sized up from 7.5 to 8, which i have to do with all madewell shoes. definitely recommend, if you can get past the sticker shock!
Date published: 2013-03-08
Rated 5 out of 5 by from favorite boots amazing boots that go with everything! surprisingly comfortable (walked around NYC in them all day) and the leather wears well. look amazing with my skinny skinny ankle jeans!
Date published: 2013-03-03
Rated 5 out of 5 by from Love! Love Love Love these boots! So cute and so easy and so totally worth the price!
Date published: 2013-03-01
Rated 5 out of 5 by from Great Style and Truly Made Well Love the cut of this boot. Heel height is perfect for everyday comfort and very walkable while still having enough height to flatter the legs and look good with dresses/skirts or jeggings. The quality is out of this world!! Zero break-in time. The zipper makes them easy to slip on. Jeggings tuck in nicely, but skinny jeans keep working their way out. I bought the brown leather which is a good basic bootie that I believe will last years and years and never go out of style! I also ordered the suede in "castle rock" color and although it was a beautiful olive color, and very high quality as well, I didn't think I'd be able to use them enough to justify the price. On my monitor it appeared more taupe. If a black suede is offered I will buy it instantly, or taupe or a sort of camel color. For my budget, I just didn't feel I'd get enough use out of the less neutral colors.
Date published: 2013-02-24
Rated 5 out of 5 by from Cute Boots! I wanted black ankle boots that would hold up during an NYC winter, and these fit the bill (and my budget). They look great with everything, and they're pretty comfortable for a heeled shoe. The soles are hard though, and they're very loud when I walk around the hard wood floors in my office. Overall, I'm very happy with them!
Date published: 2013-02-20
Rated 5 out of 5 by from Great comfy-chic boot This was my second zipcode boot purchase - this time full price. It is well constructed, comfortable, and chic. My three requirements for all purchases. Well done Madewell!
Date published: 2013-02-20
Rated 5 out of 5 by from Beautiful boots. The Zipcode Boots are beautiful, look great with skinny pants or dresses, are comfortable and TTS.
Date published: 2013-02-17
Rated 5 out of 5 by from Uber comfy & stylish! I wore the Zipcode boot right away! It was a 7-1/2 hour shift, no break...and I was completely comfortable ALL DAY! Absolutely love it!
Date published: 2013-01-11
Rated 5 out of 5 by from My new go-to Can't say enough about how much I love these boots. I wear them too much. I can walk for miles in these babies and still feel great. If I had to change one thing I would make the toe slightly pointier, less round, but all in all the best purchase I've made in a while. I'll wear these for years.
Date published: 2013-01-10
Rated 5 out of 5 by from Love this boot! This boot is great! I ordered two different colors to decide which one I wanted to keep and ended up keeping both pairs because I loved them so much. I am usually a size 8 1/2 or 9 and ordered the 9 and it fit great. They feel a little loose but the sides of my feet aren't rubbing against the sides of the boot so I know they are the right size. The construction is great and they look like very good quality shoes. The heal is just high enough to give you some height but I also feel like you could run around in them all day and your feet wouldn't be in pain. They look great with skinny jeans or a dress! Highly recommend!!
Date published: 2013-01-10
Rated 5 out of 5 by from love this boot After a month long search and several returns, I settled on the Zipcode boot in black. It really is a gorgeous boot. It falls at the right place on the ankle so it looks great with skinny jeans tucked in or rolled up and cropped pants that are tapered. However, I thought it looked a little too shiny right out of the box, but I'm sure with more wear, that will go away. As for size, I feel they do run a bit small and narrow. I also wish the heel was a bit shorter, but it's definitely better and more comfortable than a three heel inch.
Date published: 2013-01-09
Rated 5 out of 5 by from yes I'm not much of a heel-wearer but I got these for xmas, and they were too glorious looking to send back. They're super comfortable and easy to walk in. I would say that they run true to size in length but the width is maybe a little on the narrow side. I have a wide foot and a high arch and and I usually wear a 7.5-8. I have these in an 8 and they fit well. The brown color on the internet is a good representation of the actual color of the shoe. These are a well made and (somewhat) more affordable alternative to all those other super cool ankle boots that everyone wants. Do it.
Date published: 2013-01-09
Rated 5 out of 5 by from great quality Awesome boots, right size heel for comfort and the leather is nice, well made!
Date published: 2013-01-09
Rated 5 out of 5 by from Great boots These boots fit true to size and are very comfortable. I'm a teacher, and was able to wear them all day with no problem. They also look great and go with so many different items in my closet!
Date published: 2013-01-09
Rated 5 out of 5 by from The Perfect Ankle Boot I'd been eyeing these boots since they first appeared on the site, but the price held me back from purchasing them. After searching for a black leather ankle boot for months on other sites, I finally decided to buy these once they went on sale. I'm so glad I bought these boots. From the high quality of the leather to appearance, the Zipcode boots are close to perfection.
Date published: 2013-01-09
Rated 5 out of 5 by from Love these boots! So cute! I got them in the rustic brick color and the leather looks great. I also have small ankles and so I like that the opening is not too wide that it looks goofy on my legs. Great purchase!
Date published: 2013-01-09
Rated 5 out of 5 by from Perfect Boot! These boots are great. I ordered them when they were back ordered and were not set to arrive until the end of January. The boots ended up getting delivered a month early. The leather is good quality and should last forever.
Date published: 2013-01-09
Rated 5 out of 5 by from comfortable and versatile they are simply the most comfortable boots I own and go with just about everything. Got them after my daughter raved about her pair.
Date published: 2013-01-09
Rated 5 out of 5 by from Love them They fit great, super comfy, versatile, and high quality.
Date published: 2013-01-09
Rated 5 out of 5 by from Cute booties! So happy with these boots, I plan my outfits from the bottom up!
Date published: 2013-01-09
Rated 5 out of 5 by from Fantastic, classic boot Love these boots...I bought both colors! They are the only boots I own with a heel, I've never found a pair this comfortable before! A must buy!
Date published: 2013-01-09
Rated 5 out of 5 by from Great stylish boot Great style, goes well with pants and dresses. Super comfortable and fits true to size. Got so many compliments on these boots, great buy!
Date published: 2013-01-09
Rated 5 out of 5 by from The perfect bootie Just perfect. Works with everything, comfortable and look great.
Date published: 2013-01-09
Rated 5 out of 5 by from Everyday perfect bootie These are so comfortable...I literally wear them in black almost everyday of the week. A rare heeled shoe that is totally comfortable to commute in but looks great at work in NYC. Can't wait for next year's update!
Date published: 2013-01-09
Rated 5 out of 5 by from all purpose boots Since purchasing these boots, I've worn them almost everyday. They are comfortable, have a great fit, and look amazing with anything. The heel height is perfect for all day wear. I love these boots.
Date published: 2013-01-09
Rated 5 out of 5 by from Love these boots Love these boots, great fit, great color and the look great with jeans, or dresses.
Date published: 2013-01-09
Rated 5 out of 5 by from Run large The boots were high quality but ran a half size too big. Had to be returned for a smaller size.
Date published: 2013-01-09
Rated 5 out of 5 by from Fun shoe I can't pull off super trendy but this shoe is just the right amount of trendy! I prefer to wear it with skinny black leggings or with black tights/tighter fitting dress- can't seem to find pair of skinny jeans I like it with. Also looks amazing under bootcut/flared jeans. They are extremely well made (as always for madewell) and the leather is top notch. Very pleased with this purchase
Date published: 2013-01-08
Rated 4 out of 5 by from Chic little boot This boot fits well and is a perfectly manageable height, but requires a very slim pair of pants to avoid struggles with competing leg openings. They are of great quality and comfortable.
Date published: 2013-09-24
Rated 4 out of 5 by from overall great boot runs a little small and wish I had gotten half a size bigger
Date published: 2013-05-05
Rated 4 out of 5 by from great shoe, wear high socks Wear high socks, or you risk chafing around your ankles. Wish they had more padding on the bottom too, but otherwise, they're a great pair of shoes.
Date published: 2013-04-23
Rated 4 out of 5 by from Beautiful boots These boots are really stylish and overall quite comfortable, however on the first and second time I wore them around, they rubbed off the skin under my ankles. I'm hoping that the leather will stretch out a little bit because I really love the boots and for this price, they should be kissing, rather than cutting, my feet.
Date published: 2013-02-11
Date published: 2013-01-11
Rated 4 out of 5 by from I loooove em Fabulous!! Haven't taken them off since the day I got them... They just go w everything!
Date published: 2013-01-11
Rated 4 out of 5 by from Comfy & stylish! Especially for the winter when chunky boots are overdone. It's really comfy! It's a little small because I wear it with a little thicker socks but its fine! It looks good with jeans, rights and everything in between. Wearing them daily.
Date published: 2013-01-09
Rated 4 out of 5 by from Great stacked heel boot I've been looking for a short stacked heel boot forever. This one is really great, extremely comfortable, and the leather is nice and soft.
Date published: 2013-01-08
Rated 3 out of 5 by from So pretty but not comfy I had my eye these for a long time so when they were on sale I finally bought them. These are really beautiful, well made boots. The only issue I've had with them is the comfort. On my right let the top edge of the boot digs into my leg when I walk. The few times I've worn them its cause a cut- not good! So, if you can, I'd recommend trying them on in the store and walking around a bit before buying.
Date published: 2013-01-11
Rated 2 out of 5 by from A shoe that needs to be broken in! The leather on this shoe can cause a lot of discomfort at first but breaks in slowly. Helped by thick socks and Dr. Scholl's inserts for her (the thin ones used for open toed shoes), I'm able to wear them all day.
Date published: 2013-01-09
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