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The Whistlestop Sandal
full size
The Whistlestop Sandal
The Whistlestop Sandal
Product Details
Super-strappy with a sliver of a wedge and addictively soft Italian leather—it's the citified sandal you've been waiting for. Bonus: Four buckles mean there are four ways to ensure a just-right fit.
  • Italian leather upper.
  • Leather lining.
  • Man-made sole.
  • Made in Italy.
Free shipping exclusively for Madewell Insiders
*For complete details, see our Shipping Policy.

The Whistlestop Sandal

The Whistlestop Sandal is rated 4.6 out of 5 by 29.
Rated 5 out of 5 by from Wish I Could Buy Again I've had these for over two years of extreme wear. I walk nearly everywhere. College campuses, several different cities, forests, fields, and farms--I've worn them everywhere and I still get complemented on them everywhere I go. The bottoms are finally beyond repair and I wish I could buy them again. The heel height is perfect, and the fact that it's a wedge means I never have to worry about sinking into the ground. The straps provide an excellent fit and feel secure, no slipping or sliding. They can be dressed up or down. No other sandal seems to compare.
Date published: 2015-07-04
Rated 5 out of 5 by from Bought them twice! These were my fav sandals last year (I bought them in NYC) and the year before...long story short, one of the shoes got ruined in my move. I thought since I bought them two years ago that I couldn't get them again but I went online and found them again for sale (yippee) and replaced them (They don't ship internationally so I had them sent to California when I knew I'd be in town). They are comfortable and stylish and the heel is great as i'm a little short and can do with the extra inch or so it gives me. Tan leather is really strong and sturdy. Again, LOVE these sandals and highly recommend. True to Size.
Date published: 2015-01-12
Rated 5 out of 5 by from LOVE THIS SANDALS! I bought this sandal in black color about two- three years ago with original price and I really loved it! So I bought this sandal again in balck and also the brown one for next summer~ my old one is still good to wear it but wanted to buy it more for back up beacuse I cant find other sandals as good as this one!
Date published: 2014-12-29
Rated 5 out of 5 by from Favorite sandal ever These sandals are worth every penny. The leather is very soft. These will be sandals I wear with everything because the heel height is casual enough to wear with jeans yet is high enough to be a bit more formal than flats. I typically wear 6.5 in sandals but read the reviews before ordering online and opted for the 7. They are a perfect fit. I can't wait to wear them when the weather gets a little warmer!!
Date published: 2014-11-19
Rated 5 out of 5 by from I LOVE THESE! I needed a nicer pair of sandals that go with virtually every outfit i wear. I tried these on at the store and was turned off by its price. But with the sale price and the promo that I was able to apply to the order, these sandals were perfect for a poor college student! (: The first couple times i wore these, they gave me blisters but after a while the leather of these shoes stretched out to fit my feet like a pair of gloves! These are now my go-to pair of shoes even though putting them on and taking them off is kind of a hassle.
Date published: 2013-10-22
Rated 5 out of 5 by from Perfect for city walking, and cobblestone paths I live in Europe currently so there are ton of rocky cobblestone paths and hills that you do not want to come across wearing the wrong footwear, especially if you are going to be on your feet all day. These sandles have just then perfect amount of wedge to be comfortable walking around all day on a surprising amount of different terrains. Very high quality, the only reason I gave less stars is because although they are high quality, the price is too steep in my opinion. I still gave in and bought them with the help of a voucher though, and am very happy with my purchase. Like the other reviews say - these are not for people with wide feet.
Date published: 2013-07-26
Rated 5 out of 5 by from Sandals of my dreams! Eclectic, unique, timeless style. When my favorite, go-to pair of sandals sadly took their last step and snapped (literally) after hundreds of miles of walking over the years, I started looking for a replacement pair. I have other sandals, but I need that one pair that I can count on time and time again. I finally found what I was looking for in the Whistlestop sandal. I admired them on-line, looked around, came back to them and then finally found a store close enough to drive to so that I could try them on. I took the plunge, bought them, walked out of the store, put them on and then proceeded to walk in them for another several hours. After I got the arrangement of buckles and straps just right, they worked beautifully. The little bit of a wedge is sheer perfection and the straps keep my feet secured and stylish : ) I love these sandals! Cute as can possibly be on my feet and totally functional and awesomely stylish! What's not to love. They are made in Italy and the leather is divine. Thank you so much!!!
Date published: 2013-07-20
Rated 5 out of 5 by from These super versatile sandals are my go to summer shoe This is my second pair of Whistestop sandals in black. The newest rendition is well made - the leather is nice and thick and the sole seems sturdily constructed. It may take some breaking in/and or adjusting of the straps for a comfortable fit, but these sandals are incredibly versatile and flattering. I find them true to fit and like the improvements in the sandal that Madewell has made since the shoe was originally released. These will continue to be my go to sandal when I want something comfy and slightly edgy.
Date published: 2013-06-30
Rated 5 out of 5 by from Love them!! These are a little out of my comfort zone - I tend to do a flat flat (no heel) and go for more classic, less strappy silhouettes. The issue is, that sometimes my choices are predicable. This shoe is incredibly versatile, super cute, and adds just a bit of "punch" to my otherwise preppier outfits. It's incredibly comfortable, and I love that the small wedge adds a little hight and length. Love!!
Date published: 2013-06-23
Rated 5 out of 5 by from New Staple Shoe So I'm officially in love. These are my new go-to summer shoes and I couldn't be happier. Actually, they were a little out of my price range but I could tell that I'd use them often and so far it's true. Fit is perfect, the bajillion straps that take a couple wears to get used to help shape the shoe to your foot, and I'm just crossing my fingers that the leather gets a little bit softer once they're more broken in. All around happy with the purchase and stylishly decked out more frequently.
Date published: 2013-06-03
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