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Including ones from Toms, Steve Madden, and Naturalizer.
Booties—the word alone gives me joy. Once fall rolls around, I basically live in ankle boots 24/7. I walk in them, shop in them, go out to dinner in them, and I take out the trash at my apartment wearing them. It stands to reason, then, that I am always looking for the next great pair (or two, or three) to add to my shoedrobe.
Luckily, Amazon has me covered this year. As soon as I started searching for booties, there were literally thousands of pairs giving me heart eyes. However, I do have a couple caveats. First, since I walk everywhere in them, they need to be comfortable—which means flat, a low heel, or a wedge. Secondly, since I’m definitely buying multiple pairs, they have to be affordable—I’m keeping most of my picks for the year under $100.
Below are the eight booties I’m absolutely buying on Amazon this fall, starting at just $33—some of which are even on sale before Labor Day starts.
8 Editor-Approved Comfy Booties on Amazon
- Dream Pairs Chelsea Ankle Boots, $44 Dr. Scholl’s Laurel Ankle Boots, $46 (Originally $100) Soda Combat Ankle Booties, $40 Toms Clare Booties, $40 Steve Madden Leopold Chelsea Boots, $33 Clarks Maye Strap Booties, $52 (Originally $130) Lucky Brand Fayth Ankle Boots, $53 (Originally $55) Naturalizer Haley Wedge Booties, $106
Toms Clare Booties
$40 at Amazon
I will always, always love animal print everything. I especially love an animal print shoe or boot, since it can tie a look together and make a bold statement. I’ve also been a fan of Toms since the brand’s inception back in 2006, so of course I immediately gravitated toward these Chelsea booties, which are the best of both worlds.
They’re designed in a pull-on silhouette with a back pull tab and wedge heels that measure just under three-inches tall. They also have high-rebound cushioned insoles, which are partially crafted with eco-friendly content. I’m already picturing them with a little black dress and gold jewelry.
Dr. Scholl’s Laurel Ankle Boots
Orig. $100 $46 at Amazon
I don’t know why, but I have the hardest time finding brown booties that I actually like. Thank goodness I stumbled upon this Dr. Scholl’s pair, because it’s exactly what I’ve been searching for. I love the rich, caramel hue, and the Western-inspired silhouette. But what really clinched these ankle boots as an addition to my fall wardrobe is the fact that they have low-block heels, since that’s my go-to heel shape ever since I broke my ankle in two places almost a decade ago. Plus, it doesn’t hurt that Sarah Jessica Parker made Dr. Scholl’s a must-buy not too long ago.
I also wanted to make sure these booties are actually as comfortable as they look, so I headed to the reviews. One shopper, who wore them for the first time on an international travel day, said they “thought for sure [they’d] be in all kinds of discomfort a few hours into the day, but they are great.” Other happy shoppers said they were on their feet “for hours and never had a problem” and they feel “like a comfortable tennis shoe.”
Naturalizer Haley Wedge Booties
$106 at Amazon
I have a very distinctive memory of first learning about Naturalizer. I was about seven years old, and my mom took me to the store at our local Cleveland mall because she needed new, comfortable pumps for work. Even back then, I was fascinated by all of the brand’s shoes that were super stylish, yet could actually be worn all day long without pain. Is it any wonder, then, that I gravitated toward these wedge booties? I love the edgy-yet-sophisticated look of the buttery faux leather, side zip closure, padded collar, and wedge heel. They also have a soft foam lining, arch support with memory foam, and an antimicrobial sock lining, so they’re definitely as comfortable as they are cute. The ankle boots also come in light gray faux suede and chocolate brown, and sizes 5 to 11, with both half sizes and wide widths available.
These booties have racked up over 1,000 five-star ratings. One shopper with a broken foot said they could wear them to work “without limping;” other satisfied reviewers said they “give lift while still being able to walk” and they could walk all over Germany during a vacation “without any pain or blisters.”
Dream Pairs Chelsea Ankle Boots
$44 at Amazon
Kate Middleton wore Chelsea boots, so I need a pair of Chelsea boots. That’s really all there is to it. If you need a little more reason why I’m adding this specific pair to my fall style rotation, though, here you have it. They’re super versatile, thanks to the traditional style, black leather, and lug soles. I picture wearing them with leggings and a tee as easily as with a maxi dress and denim jacket. I also love the double pull tabs and elastic side gores. I’m honestly considering adding these booties to my closet in multiple colors; I also love the brown and white. They’re available in sizes 5 to 11. Shoppers said they’re “easy to get on,” “fit like a glove,” and they offer “next level style for standing out amongst the crowd.”
Shop more of my picks for affordable booties on Amazon, below, including styles from Clarks, Steve Madden, and Lucky Brand.
Soda Combat Ankle Booties
$40 at Amazon
Steve Madden Leopold Chelsea Boots
$33 at Amazon
Clarks Maye Strap Booties
Orig. $130 $52 at Amazon
Lucky Brand Fayth Ankle Boots
Orig. $55 $53 at Amazon