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About Madewell

The Ryan Chelsea Boot
full size
The Ryan Chelsea Boot
Product Details
A sexy stacked-heel version of our time-tested Chelsea boot in a supple leather that will just get better with age. Please note: When you select your size below, "H" equals a half size.  
  • Leather upper and lining.
  • 3" shaft height (based on size 7).
  • 9 3/5" shaft circumference (based on size 7).
  • 3 1/5" heel.
  • Man-made sole.
  • Import.
  • only.
Free shipping exclusively for Madewell Insiders
*For complete details, see our Shipping Policy.

The Ryan Chelsea Boot

The Ryan Chelsea Boot is rated 4.5 out of 5 by 17.
Rated 5 out of 5 by from Just buy 'em! These booties are really nice. I picked them up when they were 20% off a few weeks ago, and have worn them a few times now. They always, always get compliments. They're truly very attractive shoes, and the contrast heel is perfect. I ordered a 6.5, which is my normal size, and these run slightly small. I don't think I would have wanted a 7, but take care if you plan to wear very thick socks with these.
Date published: 2015-11-23
Rated 5 out of 5 by from Best black bootie ever! I am a sucker for black booties, and these have quickly become my favorites. The heel is just the right height so I can walk in them all day and night. It takes a couple of wears to break them in, but they are surprisingly SO SO comfortable. They run true to size, I tried them on in-store before purchasing online. Absolutely love them and recommend them, they are so versatile they go with everything! Thanks Madewell!
Date published: 2015-11-16
Rated 5 out of 5 by from The Perfect Boot LOVE these boots. I am usually the shortest person in the room and these boots give me a nice boost without hurting my feet. I was on my feet all day at work in these and felt just fine. They look great with jeans and the color is amazing. I would definitely recommend these boots.
Date published: 2015-11-16
Rated 5 out of 5 by from Awesome It is nearly impossible to find the perfect black bootie, and there are definitely more than one kind in my closet. The Ryan boot is the perfect heeled Chelsea boot - I love that the wooden heel provides a nice contrast to the black leather, creating a different and sophisticated look than your standard black bootie. It's just high enough to elevate your look (literally) but the chunky heel is comfortable and the rubber sole does a good job of absorbing impact. I've been wearing them out of the box at work all day and my feet feel great! No rubbing or pinching anywhere. Just what I was looking for.
Date published: 2015-11-12
Rated 5 out of 5 by from Amazing booties!! These boots are wonderful! Excellent quality. Brazilian made. Extremely comfortable. All bonuses.
Date published: 2015-11-02
Rated 5 out of 5 by from Classic chelsea look - can be dressed up or down Full disclaimer: I'm a sucker for black booties. Prior to this purchase I already had a pair of flat black booties and heeled black booties with solid black heel. This bootie treads is really versatile with the contrast wooden heel. Paired with black jeans, it's super elongating and can work for going out or for a more pulled together casual brunch look. Leather is supple but like others said, I agree that the high slope causes a few aches the first few wears. Overall, pretty comfortable and really well-made. Wardrobe staple...can't wait to wear it through the winter.
Date published: 2015-11-02
Rated 5 out of 5 by from Boot heaven These are beautiful, well-made boots with leather linings. I love the stacked wooden heel and shape of the toe. I got these on sale for a steal, but even at the full price for the high quality they're worth it. I'll be wearing these cuties all winter long!
Date published: 2015-10-31
Rated 5 out of 5 by from PERFECT Ankle Boot Guys - these boots are amazing. I always tend to pass up ankle boots because they usually have a heel that is just slightly too short, and on my tiny feet makes my feet look like tiny pegs (anyone catch the "Friends" reference?) So I went on the hunt for a boot with a solid, tall, stacked heel, and there were love at first sight (online). Tried on the all black stacked booth in-store, and tried basically every boot Nordstrom sold on to see if I could settle for a more affordable option, but ended up giving in when these briefly went on sale! They look incredible on, and the wood tone heel is a little darker than it looks in the picture, but the brown and black mix helps them go with my tan zip transport tote. I should note: These slope really steep on the foot, so while my heel and toesies were perfectly fine, the tops of my feet were very sore the first couple of wears - nice quality leather will stretch a bit, though! Worth every penny!
Date published: 2015-10-30
Rated 5 out of 5 by from I've been looking for this boot This boot has the higher heel that I wanted but is truly comfortable, I suspect because of the thicker (but still attractive) heel. The chestnut color is a bit darker in person than it appears online but is still great and very versatile. The wood in the heel is a little raw looking - I think on purpose- that wasn't clear to me from the pictures but it gives the heel a nice slightly worn-in look which I like.... not messy, but doesn't look "too new" either. I'll be wearing this boot to work and on the weekends. Overall a home run.
Date published: 2015-10-20
Rated 5 out of 5 by from Love! I'm literally wearing these boots right now! I live in NYC, which means I literally walk everywhere. These boots are so comfortable and stylish!!! These are by far the most comfortable boots I own. They are true to size, feel like they have a cushion when you walk....I'm talking ---- walking consecutive 12 hour workdays on a busy newsroom floor in these boots and my feet are fine. I'd definitely recommend these.
Date published: 2015-09-29
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