10 Ankle Boots I Plan to Live in This Fall, and They’re All on Sale at Amazon

Boot season is almost here, which means I’ve already started taking stock of what’s in my closet. Much to my dismay (and slight excitement, if I’m honest), a few of my go-to pairs have seen better days after many years of use. As much as I love wearing riding boots, I’m actually looking for new ankle boots because they’re easier to put on and pair better with my more casual outfits. So, I did the hard work for all of us by diving into Amazon’s Labor Day sales to find 10 ankle boots to add to my wishlist and to put on your radar, too.  

Best Amazon Ankle Boot Labor Day Deals

• Lucky Brand Basels Ankle Bootie, $67 (was $130)
• Sperry Saltwater Emboss Wool Boots, $52 (was $110)
• Dream Pairs Suede and Faux Fur Ankle Boots, $36 (was $47)
• Kenneth Cole Reaction Side Way Ankle Bootie, $33 (was $79)
• Aldo Noemieflex Block Heel Ankle Boots, $70 (was $140)
• Cliffs by White Mountain Duena Boots, $30 (was $75)
• Dr. Scholl’s Shoes Rate Ankle Boots, $49 (was $90)
• Clarks Maye Strap Ankle Boots, $62 (was $130)
• Ryka Noelle Chelsea Ankle Booties, $52 (was $80)
• Lifestride Black Ankle Booties, $54 (was $90)

Labor Day typically arrives just before everyone starts wearing boots on an everyday basis, which means it’s one of the best times to score popular pairs on sale—and I found cute styles at Amazon that are up to 60 percent off right now. My most-worn ankle boots are a brown leather pair that look just like this minimal heeled style by Lucky Brand that are 48 percent off, and I also love these Kenneth Cole Reaction booties because they’re so low that they almost resemble a pair of loafers. Although I’m not quite ready to start thinking about winter, I actually found two warm ankle boots worth highlighting and shopping: the Sperry Saltwater Emboss Wool Boots and the Cliffs by White Mountain Duena Boots. There are so many more comfortable and on-trend pairs below from brands like Aldo, Dr. Scholl’s, Clarks, and even Ryka, so make sure to keep reading while sale prices start at just $30.

Lucky Brand Basels Ankle Bootie

These Lucky Brand Basels Ankle Boots are my top pick from the options that I’ve found because they closely resemble a pair of boots I love that I’ve had the hardest time replacing. I prefer when ankle boots don’t have a heel, and these tick that box. Plus, I think that side zippers are essential for making boots quick and easy to take on and take off, and this pair has zippers on either side of each shoe for added function and style. I’m most intrigued by the Toffee color, but there are a whopping 59 other colors and patterns to choose from in standard whole, half, and wide sizes 5 to 13.  

Sperry Saltwater Emboss Wool Boots

I picked up a pair of Sperry Saltwater Emboss Wool Boots before our first snowfall in Philadelphia, and I’m so happy I did. They’re made from 100 percent leather on the upper part of the boot with a rubber “shoe” on the bottom, and the combination is waterproof. The boots are durable during rain, sleet, and snow, and my feet feel extra warm thanks to the fleece lining that’s included inside, too. I highly recommend these, and I can’t believe they’re on sale for just $52. 

Dream Pairs Suede and Faux Fur Ankle Boots

I’m amazed that these Dream Pairs ankle boots are on sale for $36 during Amazon’s Labor Day sale. The short length means they should be easy to put on, and the suede exterior and faux fur lining will add plenty of style and warmth for cold winter days. Shop this pair while it’s available in sizes 5 to 11 in colors like black, chestnut (pictured above), gray, red, taupe, and sand. 

Kenneth Cole Reaction Side Way Ankle Bootie

My style doesn’t always lean modern or minimalist, but I do always admire super low ankle boots like this 58-percent-off Kenneth Cole Reaction Side Way style that’s available to shop in eight colors and one leopard pattern in standard whole and half sizes 5 to 12. The low ankle boots are made from 100 percent suede, which is a great texture for fall and winter, and they have 1.5-inch heels to help to dress them up. They also include a handy zipper on the back that’ll look so fun when paired with your favorite pair of jeans. 

Aldo Noemieflex Block Heel Ankle Boots

It’s not often that I reach for a dressier boot, but if I was working from an office or had dinners out on my calendar, I would scoop up these Aldo block heel ankle boots while they’re quietly on sale for 50 percent off. The leather boots have a side zipper to make them easy to slip on and slip off, and the block heel helps to dress them up without making them uncomfortable. Shop for a pair in sizes 5 to 11 in six colors like black, cognac, and white, and style them with everything from dresses to jeans throughout the season. 

The on-sale Labor Day prices for popular ankle boots at Amazon won’t last for long, so join me and restock your closet with new comfy everyday favorites, like the ones highlighted above and the additional options noted below, that you can wear all season and for years to come.

Cliffs by White Mountain Duena Boots

Dr. Scholl’s Shoes Rate Ankle Boots

Clarks Maye Strap Ankle Boots

Ryka Noelle Chelsea Ankle Booties

Lifestride Black Ankle Booties