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The Charley Boot
full size
The Charley Boot
The Charley Boot
The Charley Boot
Product Details
Rich leather and suede come together for a best-of-both-worlds boot you'll want to wear with everything: skinny jeans, short skirts and anything in between. Please note: When you select your size, "H" equals a half size.  
  • Hits at ankle.
  • Leather, suede upper.
  • 9 3/4" shaft height (based off size 7).
  • 9 3/4" shaft circumference (based off size 7).
  • 1 3/4" stacked heel.
  • Leather lining.
  • Man-made sole.
  • Import.
Free shipping exclusively for Madewell Insiders
*For complete details, see our Shipping Policy.

The Charley Boot

The Charley Boot is rated 4.5 out of 5 by 73.
Rated 5 out of 5 by from Perfect! I honestly can't rave about these boots enough. They're easy to wear with anything and super comfortable. I'm a teacher and wore them all day in the classroom (standing up and running around!) and they were super supportive and comfy! I highly recommend.
Date published: 2014-09-12
Rated 5 out of 5 by from I have this boot in black and love it; wear it all the time This boot is so cute. I love it and totally recommend. I have it in black.
Date published: 2014-09-11
Rated 5 out of 5 by from Please bring the black ones back! Love these boots. Would buy them in black -- they were available last season!
Date published: 2014-09-02
Rated 5 out of 5 by from The one I've been looking for... I am so in love with these booties. I have short, athletic calves so I'd been looking for a while for booties that don't cut my legs off. These booties hit just below my ankle, so they work well with jeans as well as skirts and dresses. The quality is great and even though there's a small heel, it feels like I am wearing flats. They're super comfortable and there was no breaking in period. I don't care too much for the look of tall black boots, so these really filled a whole in my wardrobe.
Date published: 2014-01-12
Rated 5 out of 5 by from Great boots! I have been looking at these boots for a long time. I finally purchased them in the cigar color and couldn't be more happy with them! I am typically a size 8 and ordered a size 8. They fit perfect. The only problem that I've had is on my right side the boot rubs my ankle bone weird. I don't think it's a manufacturing defect but just my ankle.
Date published: 2014-01-09
Rated 5 out of 5 by from Flattering This boot has much more of a heel than shown from the angle in the picture, but is still comfortable and wearable, and I am not a heels person. The quality is excellent.
Date published: 2014-01-08
Rated 5 out of 5 by from Best little booties ever! I love these boots so much, I have them in both colors. They're true to size, well made, and super cute. The only issue is that they can feel a little wobbly for some reason when I walk, but that's probably just my issue. I highly recommend them to everyone!
Date published: 2014-01-07
Rated 5 out of 5 by from Perfect black boots! I finally found my favorite black boots! They are flat with a bit of a heel, comfortable, beautiful, and affordable! What more can I girl ask for? So happy with these!
Date published: 2013-12-25
Rated 5 out of 5 by from Beautiful boots These boots are very nice and go with everything. Highly recommended.
Date published: 2013-12-15
Rated 5 out of 5 by from LOVE LOVE LOVE This is the best purchase I ever made and very comfortable right from the start. Fits true to size but so versatile and cool that it goes with anything and everything. Very Comfortable, great value and I highly recommend it---
Date published: 2013-12-09
Rated 5 out of 5 by from Fantastic boot - a must buy! I purchased these boots in a pinch when another pair I ordered for a work trip from a competitor did not arrive in time. I wore them every day in London for over a week and loved them! They were extremely comfortable and worked well with dresses, skirts and pants. Overall, an amazing shoe that fits a bit tight at first, but within the first day stretched a small bit so they are now perfect!!! I cannot say enough good things about these boots! A must buy!!!!! - Very comfortable - True to size (I am between 8.5-9, purchased a 9 and never looked back!) - Good quality - So far have held up in snow, rain and general dampness
Date published: 2013-12-02
Rated 5 out of 5 by from Is a beautiful shoe I wore them to a concert recently and they were very comfortable and not to mention looked great!
Date published: 2013-11-26
Rated 5 out of 5 by from Love! My boots arrived last week and I love them! I ordered a size 9 which is my usual size and was worried at first because they seemed very tight. I was very close to sending them back for a bigger size but I'm glad I didn't because they stretched quite quickly and now fit perfectly. They're very comfortable, and I didn't find there was any break in period. They do narrow towards the toe, so I have found they pinch slightly around one toe. They look fantastic with everything I've paired them with so far, and would definitely recommend!
Date published: 2013-11-19
Rated 5 out of 5 by from Perfect! So, so comfortable. So, so great looking. So, so perfect. No seriously. I have received countless compliments since buying these. The heel is low enough that I don't feel awkward wearing it (and I typically wear Converses!) and these shoes are super stable even on the horrible cobblestone streets of Paris. And comfortable. Did I already mention comfortable? The suede will take a bit of maintenance but eh, as long as you don't soak these in mud, they'll be fine. Love them to bits. For everyone else: buy them, you won't regret it!
Date published: 2013-11-11
Rated 5 out of 5 by from Perfect, simple and feminine I was looking for the perfect black bootie and as soon as I saw these I knew they were it! I love their simplicity and the detail of combining different textures. The heel height is perfect to dress up or down (the wood look is sleek!). They hit right at the ankle which what I was looking for. I usually wear a 6.5 or 7 so I was hesitant to decide which size to order. I opted to go for the 6.5 thinking that they would stretch a little if they felt snug. When they arrived I was disappointed because on my right foot they felt almost unbearably snug! So then I decided I needed to compare them to size 7. I ordered the 7 and they arrived today. The 7 felt good, comfortable but they slipped on my heel a little. After much thought about how comfortable I wanted my feet to be I went for the 7 and added a thin shoe liner. With the liner they are perfect! They look so adorable with my black skinny jeans!!
Date published: 2013-10-30
Rated 5 out of 5 by from Truly fantastic Actually got the brown ones after seeing them on the model wearing the rail straight jeans (it sure helps seeing them on someone). They are hands-down fantastic. My feet never hurt one bit, they’re incredibly comfortable, perfect height, and - bonus - the toes won’t “turn up” (I can’t be the only one with that problem). Love the two-tone, too. Excellent work, MW.
Date published: 2013-10-25
Rated 5 out of 5 by from Stylish. Great ankle boot. Clean cut, stylish and comfortable. I highly recommend these!
Date published: 2013-10-25
Rated 5 out of 5 by from Handsome, comfortable boot Love this boot. Stylish and comfortable at the same time. Bought them for my daughter when she admired mine!
Date published: 2013-10-21
Rated 5 out of 5 by from Love these boots The charley boot is exactly as described. You will want to wear them with everything. The heel area is quite stiff on your first try on but they quickly become very comfortable. I usually wear a 6 1/2 or 7 in a boot and the black in 6 1/2 worked for me. Awesome boots!
Date published: 2013-10-18
Rated 5 out of 5 by from My Absolute Favorite These boots are amazing. I bought them in black, and loved them so much I ended up getting the brown (brownish/green) as well. They're a little tough on the ankle, but I just started wearing them so hopefully that'll change with some wear; other than that, they are incredibly comfortable. They are so versatile and the heel height is perfect. If you're on the fence about getting these boots, I would definitely take the plunge.
Date published: 2013-10-14
Rated 5 out of 5 by from Versatile Boot Amazing Boot. Edgy enough to be stylish but also classic enough to be an everyday shoe. Love the mid-heel, which makes it great for shorts, dresses, and pants. I had been looking for a boot like this for the past year and I definitely found it.
Date published: 2013-10-09
Rated 5 out of 5 by from match everything !!! i wear it to work everybody liked it !! very good boot.
Date published: 2013-10-08
Rated 5 out of 5 by from Great black boot The suede and leather mix makes a simple black boot way more interesting. Love the height- nice with dresses and pants. It has taken about 4 wears to break them in. The first few times my feet ached after wearing them. Overall, very happy with this purchase!
Date published: 2013-09-26
Rated 5 out of 5 by from Love this boot! I have to stop myself from wearing these shoes everywhere- stylish but classic, goes with everything. They run true to size and other than a little bit of breaking in (mostly in the heel) they are incredibly comfortable to walk around in! I get multiple compliments on these every time I wear them. I got the brown on sale, would not have bought them full price, but for the sale price I am loving them!
Date published: 2013-09-24
Rated 5 out of 5 by from No break-in time These boots are so comfortable and just the right height. I was afraid I would need to break them in for a few weeks, but as soon as I put them on I walked in these shoes all day comfortably. It's only gotten better in the 2 weeks I've worn them. They run true to size maybe even slightly snug. The heel is solid so it makes a lot of noise, but you can walk miles in these shoes.
Date published: 2013-09-23
Rated 5 out of 5 by from excellent superb shoe is it i like it superb shoe is it i like it superb shoe is it i like it
Date published: 2013-09-23
Rated 5 out of 5 by from Comfiest, cutest shoe I just got these shoes when they were on sale, and I am in love! They look and feel amazing when I have them on. The heel is the perfect height for all-day wear, and the shape of the shoe does not hurt my slightly wide feet. i can already tell they will be my go-to shoes this fall, and they are going to break in nicely.
Date published: 2013-09-11
Rated 5 out of 5 by from The perfect everyday boot! These boots are the best! The heel is the perfect height, and I love the two tone leather. I'm usually a size 10 1/2, but since only size 10 and 11 were offered I opted for the size 10. They were definitely a little snug at first, but broke in quite nicely, and they fit perfectly now. I also love that I can ride my bike in them really easily.
Date published: 2013-09-04
Rated 5 out of 5 by from must-have-in-your-closet!! Perfect boot for all year-round... Great, super comfortable and of course, fantastic design!! I'll be wearing them all the time... this is my 'LBD' in shoes... I adore the contrast suede in the back... One more time, Madewell did a fab job!!
Date published: 2013-07-24
Rated 5 out of 5 by from Love this boot! This boot is so comfortable! The heel height is perfect to give you a little lift bbut not too high. I have worn them all day and walked all over Manhattan in them and my feel feel fine. My feet are a little wide so I would say they run a little narrow but the suede is stretchy so it will give some room. Great purchase! Good closet essential!
Date published: 2013-05-22
Rated 5 out of 5 by from Comfortable & Stylish These boots are extremely comfortable and can be paired with essentially any outfit. I love the different textures and wear them all the time, definitely recommend.
Date published: 2013-05-17
Rated 5 out of 5 by from 100% Satisfied I LOVE these boots. Bought the brown and have worn them a few times before springtime gets too warm. Have been in them for running errands all day and my feet weren't screaming. The style is on point and they fit like a glove. Another super Madewell product.
Date published: 2013-04-15
Rated 5 out of 5 by from So functional! love these boots - my second pair of Madewell boots (I also own the suede Zipcode. Very comfortable, and can be worn with dresses, jeans, etc. Zipper jingles a little but i imagine that will fade away.
Date published: 2013-04-11
Rated 5 out of 5 by from Very comfortable boots So comfortable that breaking it in is not necessary. They are easy to walk in, have the perfect heel height and they look good too.
Date published: 2013-04-10
Rated 5 out of 5 by from So Versatile I love the mix of textures on this boot. They're simple, but have just enough detail to keep them from being boring. I can wear them with jeans, shorts, and dresses and they always look good. I'm a size 8.5-9, so I got a 9 and they fit perfectly.
Date published: 2013-04-08
Rated 5 out of 5 by from Daughter loves the boots Purchased for my 28 year old daughter living in Brooklyn, NY for her birthday. She loved them, and I was pleased with the quality of an American product.
Date published: 2013-04-02
Rated 5 out of 5 by from Amazing boot! love this boot... it fits great, super comfortable. it looks great with a dress and tights, but also looks casual with denim.
Date published: 2013-01-25
Rated 4 out of 5 by from Good looking bootie! This casual boot is great looking and fits TSS and fine for a bit wider foot although they will stretch. The height is just enough to make it work wth skirts and dresses. Overall a great purchase on sale.
Date published: 2015-01-11
Rated 4 out of 5 by from Stylish yet comfortable Loved the look of the boot and relatively low heel height. Perfect with both skirts and skinny jeans. Fits true to size. Minor issues are that you need very low socks to wear with boot and the inside zipper can hit on the ankle bone. Otherwise, great style and wearability.
Date published: 2014-12-30
Rated 4 out of 5 by from Bring back the black leather Please, pleeease bring back the all leather!!! I have the brown suede, but never got around to getting the leather. The low heal and simple design make it so versatile. I love the fit and comfort of this boot. No breaking in time. I'm assuming the collar-stud version replaced it? It doesn't compete. Please! :)
Date published: 2014-11-13
Rated 4 out of 5 by from Chic but different! Just wore these (night vision colored) boots for the first time yesterday. They were relatively comfy, but my feet were a bit sore after a couple of hours standing on my feet. I'm sure in time the leather will "give" a bit and they will become more comfortable. I received compliments all day long on them. People loved that they were two tone leather and suede and the two colors. Very stylish and chic looking, while still looking classic and up to date! Love these!
Date published: 2014-10-31
Rated 4 out of 5 by from Love the two tone! This is my 4th attempt at a low heeled ankle boot this season, all the others got returned for various reasons. Tried others where the ankle gap was too big to wear with skinny jeans, others that were too slim in the ankle opening so they looked too dressy. These fit the bill just right! I've been able to wear with skinnies, jeggings, cuffed boyfriends, and they look perfect with every pair.My favorite jean pairing so far has actually been Madewell's Skinny Skinny! I got the Navy/black combination boot and it has just enough interest to not look like other boots on the market. I would say they run about 1/4 size large, not enough to size down but definitely enough to consider what type of sock you will wear with them. Also, since the ankle rise is so short, expect a little heel slippage. Nothing you won't get used to but I think it comes with this shape of low ankle boot. I only gave it 4 stars because I want another pair but the color selection is not great!
Date published: 2014-10-29
Rated 4 out of 5 by from simply stylish low boot I was glad to see this offered again on sale as I missed it last year. Fun two-tone color and texture with bold zipper. Got the blue/black version, which might look even better if the heel and sole were also black. Very pleased with the fit and especially the height of the heel, not flat, but still comfortable and good for walking.
Date published: 2014-09-30
Rated 4 out of 5 by from Beautiful but hard to break in I love these boots, they are gorgeous and go with anything. However, when I first got them they were almost impossible to wear. I don't consider my feet to be wide, but the toe area was extremely tight at first. The leather is pretty stiff. I had to very slowly break these in, like a couple hours of wearing at a time max. They are still a little snug in the toe area but are getting more comfortable with each wear.
Date published: 2014-09-14
Rated 4 out of 5 by from A Must Have Since these boots first came out, I have been in love. I find that the leather and suede combo is great to pair with jeans during the day, and fabulous with a skirt and tights for drinks with my girlfriends. I usually don't pick boots that cut off at the ankle as I don't think that height for a boot looks particularly flattering for me, and these boots proved me wrong. I also like how the heel is a little higher so it gives you a little lift. They did run a little small. I usually wear a 8.5, and I had to buy the 9. My only issue with this shoe is that if I am wearing a shorter sock, the seam on the top inside rubs on my ankle and it can get very uncomfortable. So either carry band aids, or wear a higher sock. Otherwise, a must have boot that will be a great addition to any closet.
Date published: 2014-02-18
Rated 4 out of 5 by from Loved this boot but not for me. I tried this on in the store and loved it but had to order in my size. It's a very firm boot-- will need a considerable breaking in period. It's well made, but could use a softer sole or cushioned insole. I had to return them as they were too uncomfortable for me. It runs small; I'm narrow size 6...the 6.5 pinched my toes too much to wear with socks and you'll need socks. I had been looking forward to this good looking boot, sadly it didn't work for me but may for others...I hope,so as it's a winner.
Date published: 2013-12-18
Rated 4 out of 5 by from perfect for short people I'm incredibly short, so ankle boots usually cut my legs off making me look like i have stubby legs. These boots hit at just the right height below my ankle. The black definitely look to be better quality than the brown (i ordered both but returned the brown). Super comfy and definitely stretch out with wear.
Date published: 2013-12-01
Rated 4 out of 5 by from Have received many complements Love the look. They are fairly comfortable but would not want to walk around all day in them. The heel is just right for me as I'm not young, but they are still stylish. Can wear these (brown) with all my pants and do so.
Date published: 2013-11-28
Rated 4 out of 5 by from Great boot Love the style of this boot! Had to go a half-size up, and they need to be broken in a lot, but otherwise perfect!
Date published: 2013-11-18
Rated 4 out of 5 by from great boot, well made I've been looking for a good ankle boot for so long–so long!–and I found charley. The heel in leather protects it from driver's skid, and is quite smart to boot (!).
Date published: 2013-10-28
Rated 4 out of 5 by from Love the look and comfort of these boots. I own the Zipcode boots from a year ago. Compared to that boot, the toe is narrower (it's a bit pointier but not like the Barnwood boot is) and the heel is lower. I love the low heel, I can wear these standing on my feet all day at work without feeling too sore. The height of the boot is lower as well, it hits right at my ankle. In the beginning, if I wore really low socks, the right boot would cut into my ankle and bleed. I tried to wear socks that hit right at the ankle instead. After breaking them in for a bit, I feel fine wearing lower socks. The black suede also tends to get scratched up near the toes. I understand that this happens but because these are black the scratches are much more prominent. I'm wondering if there is some suede polish to help fix this. Lastly, the heel cap is made of plastic. I've slipped a few times walking down a hill or wet ground. Probably a good idea to get them re-heeled with a rubber heel but I like the click clack sound :)
Date published: 2013-10-08
Rated 4 out of 5 by from STYLISH Awesome boot. Very stylish and different. Can wear with jeans and dresses Heel height is just right. It runs small. I wear 6H-7 and they're still a bit tight. I exchanged them for 7H. Hope it will work...
Date published: 2013-08-06
Rated 4 out of 5 by from Awesome Boot! Was a little nervous at first because of the stiffness of the boot, but I was able to break it in really quick, and now I can't stop wearing them! I'm afraid the heel quality will wear soon, but still an awesome boot.
Date published: 2013-05-21
Rated 4 out of 5 by from Great look, a bit hard inside I bought the Charley in the tan color. It goes very well with my wardrobe, but is a bit stiff on the inside. It's hard to stand in these for a long time. Because they're on the tighter side, it's also hard to add insoles. Still love them though and would recommend them!
Date published: 2013-05-18
Rated 4 out of 5 by from Made for walking Read the other reviews and was concerned about the width, but the boots are fine and true to size, for my feet anyway. Very comfy and a bit western-ish in style, so i've been told. I walk a lot, and there is zero pain in these booties.
Date published: 2013-04-12
Rated 4 out of 5 by from Trendy + casual These boots look great dressing them up or down. They are quite narrow like other reviews mentioned previously though
Date published: 2013-04-09
Rated 4 out of 5 by from great looking boot these boots look great and they have great versatility but because the toe box is narrow they are slighty uncomfortable.
Date published: 2013-03-29
Rated 4 out of 5 by from Unique boot I bought these boots because I have the zip code boot and love love love them. I wanted a boot with a shorter heel and these had a unique look that I couldn't pass up. They run narrow which was a plus for me but fit awkwardly on my feet. I outfitted them with some cushioned padding at the heel and they are a perfect fit now! I love them with skinny jeans and am looking forward to trying them with dresses this spring. The style works for so many looks. Would recommend to anyone interested in them!
Date published: 2013-03-08
Rated 4 out of 5 by from Boots were lovely but too narrow I bought these boots based on the size I have been in other Madewell shoes and boots (size 7.5). However, these boots were very narrow. As I have very narrow ankles and feet, I was very surprised to find that these boots were far too narrow for my feet. Also: note that there is no rubberized grip or tread on the bottom of these boots, so not the best for icy or cold conditions. Although I loved the look of these boots, I had to ship them back.
Date published: 2013-01-23
Rated 3 out of 5 by from Love the look, but ouch. I wanted so badly to make these work. The two-tone leather is very unique and these have exactly the look I was after, but I just couldn't allow myself to spend that much money on a shoe that I KNEW would be uncomfortable. I don't understand the reviews saying how comfy these are--the leather, while very beautiful, is super stiff and bothered my ankles just wearing them around the house. Sadly, they had to go back.
Date published: 2013-11-22
Rated 3 out of 5 by from "Italian made" How can Madewell say "italian made"? When I received these boots the label said made in Romania. This is false advertising. The price cannot be justified for "made in Romania"
Date published: 2013-03-02
Rated 2 out of 5 by from Stiff leather, heel looks like plastic When I compare these booties to the Madewell Zipcode suede booties (which I've had for over a year), the difference in comfort and quality is drastic. The Charley has stiff, hard leather that ends at a lower position on the ankle than the Zipcode and digs in in all the wrong places. I also found that the stacked heel on the Charley looks cheap and plastic. I saw these Zipcodes on the model on the Madewell site and they looked so awesome so I have to say I was disappointed at the quality when I got them in the mail. Sent them back :( Maybe I'll try the Billie instead.
Date published: 2013-05-01
Rated 1 out of 5 by from Uncomfortable! Bought these in store and loved them. However, after 30 min of wearing them, the shoes were rubbing my ankles and the outside of my ankles began bleeding. Not exactly what you want in a shoe.
Date published: 2014-10-10
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