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Product Details
Just so timeless—a gorgeously straightforward flat-heel style in the richest Italian leather. Please note: When you select your size below, "H" equals a half size.
  • For the best fit, order a half size smaller than your usual size.
  • Hits above calf.
  • Italian leather upper.
  • 15 1/2" shaft height (based off size 7).
  • 14 15/16" shaft circumference (based off size 7).
  • 3/4" heel.
  • Leather lining.
  • Man-made sole.
  • Made in Italy.
  • Madewell.com only.
Rated 4.5 out of 5 by 49 reviewers.
Rated 5 out of 5 by Extended Calf runs extremely small It is unfortunate that this boot is not a true Extended Calf since it is a classic boot that is so nicely made. I was very disappointed that they did not fit, thought I finally was going to find a boot that worked for my calves. March 3, 2014
Rated 5 out of 5 by Beautiful boot! Runs small. This is a great boot but it DOES run small. I usually wear a 7 1/2-8 and the 7 1/2 was way too big. I exchanged it for a 7 and that fit me perfectly. I'm 5' 5", 120 lbs and I had to get the extended calf... I have a feeling not many people can fit the regular calf size. I will say that the first pair I got had more texture in the leather and the second pair was much more buttery and smooth—the leather will vary from boot to boot. I'm much happier with my second pair than the first. Also, I used Pay Pal to purchase these and when I exchanged them, I found out that Madewell can't exchange items using Pay Pal. So my money was refunded and I had to call customer service to re-order. Thankfully they still gave me the original price—I got them on sale. The site doesn't say anything about paying with Pay Pal so just be aware that exchanges can't be made if you pay with that method. January 19, 2014
Rated 5 out of 5 by nice boots These boots are not cheap, but they definitely look and feel expensive. The leather is really nice. They are a classic stye and I hope they last for many years. I sometimes have trouble fitting into regular boots in the calf area, and the extended calf fits me perfect. The foot part of the boot fits true to size. January 4, 2014
Rated 5 out of 5 by Simply Beautiful This is a beautiful boot. I love that there are no metal embellishments. A word about the size. I am 5'7 and my calf is 15.5" at its widest part. I have two pairs of Madewell skimmers in 8.5. I tried on the regular calf boots in the store and could not get them all the way up. Then I ordered the 8.5 and the 9 in extended calf online. The calf was still a little tight, but I was able to wear them over leggings. I ended up keeping the 8.5s, because they fit my foot better. Things have stretched out (in a good way) after 2 weeks of wear. My advise: If your calves are 15" or bigger, get the extended calf. If you already own a pair of Madewell shoes, order the boots in the same size. They are somewhat narrow, so unless you have a narrow foot, you should order these boots in your normal shoe size. January 2, 2014
Rated 5 out of 5 by Awesome riding boot This boot is the perfect pull on riding boot! I hunted high and low to find this. Fit is great. Slightly snug at first but stretches nicely. I have average athletic calves and usually find boots fit way too snug.... this one is perfect! Great quality, look, feel and fit. Super comfortable, I wear them almost everyday. December 25, 2013
Rated 5 out of 5 by 2nd Pair I bought these in the brown and liked them so much I came back for the black. The measurements given in the description are spot on. I am 5' tall, 100 lbs, but a runner, so have athletic calves and these are great over jeans and leggings. Nice quality leather. Should have these for years. December 20, 2013
Rated 5 out of 5 by 2nd time is a charm! I fell in love with them in the store but I had to order online for the extended calf ones. It was 30% off promo at that time. The 1st order came and I was disappointed. There was a defect inside one of the boot. I ordered the 2nd one on the phone outside that promo period and the CSR was kind enough to still give me 30% discount. I have worn them 3 days in a row now to work and they don't bite me at all. Normally I wear boots in size 8 and flats in size 71/2. I got these ones in 71/2 and they fit perfectly. Love them! December 13, 2013
Rated 5 out of 5 by Gorgeous boots These boots are gorgeous! The leather is sturdy but soft. They are classy and classic boots. They don't have any metal embellishments to detract from the strong, simple statement. Just a warning though, they run pretty narrow in the calf. The "Extended Calf" circumference is more like a pair of regular boots in other brands. I'm not sure why the description says to size down. I ordered my normal size and they fit correctly. December 2, 2013
Rated 5 out of 5 by So many compliments I have gotten several compliments on these boots. I bought the brown ones and they look great with everything. The extended calf helps but it doesn't make them too wide. So I still have to wear them only with really skinny jeans or tights. I highly recommend these awesome boots! November 23, 2013
Rated 5 out of 5 by classic look I hesitated to spend this much money on a pair of boots, but I am happy I did. I love the classic look and comfortable fit. As recommended, I ordered 1/2 size smaller. I would consider buying another pair. November 18, 2013