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The Charley Boot in Leather
full size
The Charley Boot in Leather
The Charley Boot in Leather
The Charley Boot in Leather
Product Details
Our popular ankle boot remade in rich leather for a look 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.  
  • Leather upper.
  • 9 13/16" shaft height (based off size 7).
  • 9 13/16" 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 in Leather

The Charley Boot in Leather is rated 4.5 out of 5 by 13.
Rated 5 out of 5 by from Please bring this awesome boot back!! I love this boot and want it back for 2015! The Cait boot is similar, but I don't love the suede... and would much prefer to buy this boot again for this year. I wore my last pair out!!!
Date published: 2015-10-13
Rated 5 out of 5 by from Please bring this boot back! Such a versatile boot to wear with dress, skirts and skinny jeans! I really want to buy this pair over the suede version so I can wear it in all weather.
Date published: 2014-11-26
Rated 5 out of 5 by from Exceptional Boot! When I first wore the boots, they were a little narrow in the toe area. After a few days the shoes were perfectly stretched! The leather is excellent quality, and it seems like these boots will last for a long time.
Date published: 2014-10-31
Rated 5 out of 5 by from Love this boot - please make it in brown! I love this boot, excellent quality and perfect height heel. I like the smooth leather version better then the suede. Madewell, please make more of these in the smooth leather and please make it in a brown color like a few of your other boot styles - pecan or English saddle, please, please!
Date published: 2014-10-15
Rated 5 out of 5 by from Excellent fall staple! These boots are amazing! Very high quality and it only took a day of wear to break them in, I guess you can say they're well made ho ho ho. They're extremely versatile, I wear them with skirts and dresses and jeans. Like others, I was interested in the Billie Boot but these are way more practical for walking across a college campus. The best part is that I wasn't in pain after a day of walking! Get these boots before they inevitably sell out!
Date published: 2014-10-04
Rated 5 out of 5 by from Great boots! These fit perfectly and look great. They took a couple days to break in but now they are fine. I have thick ankles so the top opening rubbed a little, but the leather stretches. I can tell these are just going to get better with more wear. I had wanted the billy boots for a long time, but when I saw these in all leather, they were like the billy boots' more practical younger sister. A great happy medium, and a slightly better price point. They are great shoes for teaching. You can wear them with casual outfits or go more business casual with cropped trousers or a midi skirt. Perfect addition to my fall wardrobe.
Date published: 2014-09-19
Rated 5 out of 5 by from classy and versatile I really love this boot! It's so classy and versatile. It wears well with just about everything in my closet and it's surprisingly comfortable. I also own the Billie Boot, and I like that the heel is lower on this pair. I usually wear a size 9-1/2 or a 10, but the 9 fit for me. It was a bit snug in the toe, but has molded to my foot really well with wear. This boot is definitely a great investment!
Date published: 2014-09-18
Rated 5 out of 5 by from very comfortable with a nice heel height. This boot is very comfortable and true to size if not ever so slightly roomy which will allow room for warm socks this winter. Great heel height for walking all day.
Date published: 2014-09-16
Rated 5 out of 5 by from Refuse to take them off I have these in the brown suede and leather from last year and wear them nearly everyday. I decided to invest in a second pair in the black leather. They are the same comfort that I know and love but the black leather has a whole different feel. They don't need any breaking in, super comfortable and look amazing with practically everything. I can't wait to wear with my motorcycle leather jacket when it gets a little cooler! Don't even think about buying these boots, just do it! You will not regret it for a second!
Date published: 2014-08-19
Rated 4 out of 5 by from Perfect bootie! I was looking for a black ankle boot to wear with both skinny and boyfriend jeans- and maybe some skirts if I'm feeling fancy- and these were my favorites of all the (hundreds of) pairs I looked at. They're basically perfect. They're comfortable, but are a bit stiff.
Date published: 2014-10-16
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