Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission
Madewell—the one-stop shop for chic, cozy, and practical clothing, shoes, and accessories—is no stranger to sales. Just last month, the brand hosted its fall insider sale to give us a jumpstart on our autumnal wardrobes, and an end-of-summer sale this past July. This time around, the retailer is hosting another seasonal sale. In addition to discounted plaid shackets, chunky knits, and flare denim, the price tag on fall boots is being slashed during Madewell’s fall sale.
These boots aren’t your typical shoe. They’re actually comfortable thanks to the fluffy insoles that are so soft, it’s feels like you’re walking on clouds. We’ve combed through the sale, and we can confirm there are some worthy selections, everything from cheetah-print statement boots to chunky combat boots. From now until October 26, you can save big (25 percent off $100+ or 30 percent off $200+) on fashionable and functional boots.
When checking out, don’t forget to use the code GOSPREE, so you don’t miss out on additional savings. Without further ado, scroll down to see some of our favorite styles. Alexa, play “These Boots Are Made for Walkin'” by Nancy Sinatra.
The best boots of Madewell's fall sale
The Rayna Lace-Up Boot — $142.00
Originally $198, now $142
Don’t let these military-style boots fool you. They may have a hard appearance on the outside, but on the inside, the boot is cushioned with thick padding, making it feel like you’re walking on pillow-y clouds. Crafted out of leather and a chunky sole, the shoe is both stylish and comfortable. Throw it on with anything for a utility look.
Sizes available: 5-12
Colors and patterns available: 4 (2 on sale)
The Citywalk Lugsole Chelsea Boot — $105.00
Originally $210, now $105
Everyone needs a pair of statement boots, and this Citywalk pair will have you ready to hit the pavement. The outer layer is made of textual calf hair, and the footbed is constructed out of the same cloud-like cushioning as the Rayna lace-up boot for ultimate comfort. It pairs well with denim and a chunky knit for when temperatures plunge.
Sizes available: 5-7
Colors and patterns available: Pecan Shell
The Henry Lug-sole Boot in Suede — $77.00
Originally $228, now $77
If you’re looking for a sturdy, commute-to-work boot, look no further than the Henry lug-sole boot. It has a thick, grippy sole that can handle stairs, concrete, and any rough terrain, aka under-construction streets. The front and back pull tabs make it easy to slip on and off. Plus, it has a zipper for even easier access.
Sizes available: 5-12
Colors and patterns available: Distant Sand
The Carina Platform Chelsea Boot — $153.00
Originally $219, now $153
Heeled booties don’t have the best rep when it comes to comfort, but that’s not the case with the Carina boot. The cushioned insole and the chunky sole cushion your feet with each stride. It also helps that the boot is just really gorgeous, thanks to the leather outer.
Sizes available: 5-12
Colors and patterns available: 3 (2 on sale)
The Carsen Boot — $132.00
Originally $198, now $132
This hiking-inspired bootie will have you taking your feet to new heights. The boots are lined with soft jersey to keep your toes warm, and the water-resistant upper protects your feet from wind and snow. Even more, it’s cushioned with thick padding for a little extra oomph.
Sizes available: 5-11
Colors and patterns available: glazed pecan
The Dani Chelsea Lugsole Boot — $146.00
Originally $218, now $146
No fall season is complete without a Chelsea boot, and this pair takes a fun spin on the original. Featuring a chunky sole, cushioned insole, and leather outer, the Dani boots are stylish and super comfy to walk in. The pull tab and stretchy, neoprene inserts make heading out of the house a breeze.
Sizes available: 5-11
Colors and patterns available: 2
The Zip-Up Lugsole Rain Boot — $49.00
Originally $88, now $49
When it pours, throw on these zip-up booties. Made of rubber, you can weather any storm in these boots and stay completely dry. It also features a pillow-like insole for extra comfort.
Sizes available: 5-11
Colors and patterns available: 3 (2 on sale)
The Lace-Up Lugsole Rain Boot — $53.00
Originally $88, now $53
A lace up version of the lugsole rain boot, these booties are perfect for someone who wants a more fitted feel. Featuring the brand’s signature CloudLift insoles, the boots will help you get from point A to B in comfort. Plus, they’ve been storm tested to ensure no water leaks.
Sizes available: 5-11
Colors and patterns available: 2
Want to be the first to hear about the latest (and greatest) SHOP product drops, custom collections, discounts, and more? Sign up to have the intel delivered straight to your inbox.
Sign up for the Well+Good SHOP Newsletter
Get exclusive deals on wellness, beauty, fitness, and food products that have been hand-picked by our editors.
Got it, you've been added to our email list.
