This Just In


Looks We Love

The Getaway Shop

Labels We Love

The Madewell Essentials

Monogram It


Your double-tap-worthy pics

From denim recycling to
beach cleaning












intimates & pajamas



extended sizes

shoes, bags &


(see all)

oxfords & loafers
rain & cold-weather boots







The Scenes

Our Blog





About Madewell

The Ainsley Chelsea Boot in Leather
full size
The Ainsley Chelsea Boot in Leather
The Ainsley Chelsea Boot in Leather
Product Details
In rich, smooth leather (right down to the easy-to-break-in soles), this modern Chelsea boot has a pared down look that makes it a design-team favorite. Meet your new wardrobe MVP. Please note: When you select your size below, "H" equals a half size.
  • 3/4" heel.
  • Leather upper, lining and sole.
  • Import.
Free shipping exclusively for Madewell Insiders
*For complete details, see our Shipping Policy.

The Ainsley Chelsea Boot in Leather

The Ainsley Chelsea Boot in Leather is rated 4.5 out of 5 by 42.
Rated 5 out of 5 by from Bootie of the season I ordered these in size 8.5, which is my regular size in boots/booties. The cognac color is beautiful! There was no "break in" period necessary as these are utterly comfortable. I have wide feet so the shoes were slightly snug initially, but the leather softened after one wear. I love these booties! I've been wearing them non-stop ever since I received them in the mail last week. I love them so much I might buy them in black too.
Date published: 2017-11-17
Rated 5 out of 5 by from These are the chelsea boots you've been looking for I'm an in-betweener: a 6 in flats and 6.5 in heels. I attribute this to my narrow feet. I purchased the size 6 and the leather settled in after a weekend of wear. I tried on both sizes in store- the 6.5 was fine but it felt loose. The 6 hugged my feet perfectly but I second guessed myself because I was told the boot was true to size. I took a leap of faith and went with the smaller size because my main personal complaint for chelsea boots were that they were usually too loose in the ankle and fit. The look is amazing, materials are great, and the boot looks very streamlined. I've searched high-low for my perfect Chelsea boot and I think I've finally found it! If you're looking for a chic Chelsea boot and have narrow feet like mine, go with your 'flat shoes' size!
Date published: 2017-11-16
Rated 5 out of 5 by from LOVE! I originally purchased these in a 7.5 but found they were too small. I exchanged for an 8 and I am absolutely in love with these boots. They are the perfect fall boot and closet staple.
Date published: 2017-11-06
Rated 5 out of 5 by from perfect chelsea boot This is the chelsea boot I've been looking for. It's super classic and just right.
Date published: 2017-10-26
Rated 5 out of 5 by from The perfect flat boot Like a previous reviewer, I also bought these boots to alternate with a paired of 2"+ heeled black booties I purchased last year. I am in love with them. They look great with casual and work clothes, and are perfect for us city dwellers who do a lot of walking. I typically wear boots with thin socks or tights, so I purchased my normal size and found them true to size. They initially felt narrow, but loosened up after a single wear.
Date published: 2017-10-17
Rated 5 out of 5 by from Perfect + Simple Perfect perfect perfect. I typically wear an 8.5 in shoes, but always size up a half size when buying boots so that I can comfortably wear thick socks when it's cold. I purchased a 9 and they were perfect for that reason. Highly recommended for comfy, simple, goes-with-anything boots!
Date published: 2017-10-16
Rated 5 out of 5 by from Comfortable I got these in the brown and might also get the black if they aren't sold out. Comfortable shoes are really important to me lately, and these are right out of the box. They will look good with pants, and even decent with tights and a dress. I wear 6.5 and that size was perfect -- can fit a light sock, too.
Date published: 2017-10-10
Rated 5 out of 5 by from Gorgeous boot, but slightly narrow So excited to wear these! The quality of the leather is great, and the vintage redwood color is as pictured. I ordered a 6h and they fit TTS lengthwise. I have pretty narrow feet and these fit a bit snug even with thin socks the first time I put them on, but given that they're leather, I'm hoping they'll stretch a bit. If you have wide feet or plan to wear with thick socks, you might want to consider sizing up. The only hangup I have is that the ankle opening is fairly small. I would say my ankles are average sized, and there is barely a gap between the boot and my ankle. I'm a little worried that the front of the boot might rub uncomfortably against the front of my ankle if worn for long periods of time. But again, this might be something that stretches with increased wear. Overall I'm really happy with them and can see them being a fall wardrobe staple!
Date published: 2017-10-04
Rated 5 out of 5 by from excellent shoes This pair of shoes fits autumn and winter and is perfect for dress, pants and jeans.
Date published: 2017-10-26
Rated 5 out of 5 by from New Favorite Boot! Extremely comfortable, low heel. Can dress up or down for a great everyday look!
Date published: 2017-10-13
  • y_2018, m_7, d_14, h_21
  • bvseo_bulk, prod_bvrr, vn_bulk_2.0.8
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_42
  • loc_en_US, sid_G8069, prod, sort_[SortEntry(order=RATING, direction=DESCENDING), SortEntry(order=HELPFULNESS, direction=DESCENDING), SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_madewell