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Ankle boots are staples in everyone’s closet, just as much as a pair of blue jeans or a white t-shirt. They’re your go-to shoes when the temperatures drop, and for the truly boot-obsessed, you’ll wear them even in the summer underneath a slip dress or with denim shorts. This style comes in a variety of designs, which makes it all the more difficult to not buy every pair you see on sight. We’ll help you narrow down your bootie options for 2020, though—retailers have released their initial ankle boot offerings of the season, and the options do not disappoint. Whether you’re gravitating towards another pair of the classic black leather heeled boot or a heeled snakeskin design, the ankle boots ahead can dress up or lend a more casual air to your ensembles.
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Animal Print Ankle Boot
Serna Booties in Fawn Calf Hair
The animal print trend is alive and kicking for fall. We love this brown and white spotted Western-style bootie that goes with everything, from your skinny jeans to thicker knit skirts.
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Cotton Canvas Ankle Boot
Cotton Canvas Boots
Thick sole boots will run the footwear game this season, so get ahead of the trend by test-driving this under $100 option from H&M. It’ll give you a good idea as to whether or not you want to invest in another pair.
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Fishnet Ankle Boot
Naughtily-D Ankle Boot Black Suede Calfskin
Made in Italy, this pair of fishnet panel booties feature gold paneling against black suede. Extra design details to pay attention to include leather laces and a zipper on the back. Should you not want the gold accent, opt for the solid black pair.
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Double Buckle Ankle Boot
Ankle Boots in Leather Burgundy
For a rich color on your ankle boots, slip your foot into this burgundy option. It has an air of elegance thanks to the smooth leather finish and two polished buckle straps.
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Water-Resistant Ankle Boot
Tivoli IV Boot
For those who live in climates that warrant a more heavy-duty ankle boot, or if you just like furry shoes, get these insulated waterproof suede and leather booties. They have a no-slip rubber sole and a supportive footbed, so you can conquer that patch of black ice.
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Chunky Ankle Boot
Ranger Army Leather Ankle Boots
This ankle boot has the perfect amount of edginess, chunkiness, and sass. Whether you choose to rock it underneath your fall maxi dress or tuck your denim into the boot, it’ll make a thundering fashion statement as you walk.
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Green Rubber Ankle Boot
Rubber Chelsea Boots
Break up your black and brown ankle boot collection with this military green pick from Ganni. It can be worn on days with or without bad weather, though for the latter you can trust these booties to carry you safely across a slushy or icy street.
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Houndstooth Ankle Boot
The Cline Bootie
An easy way to work the houndstooth print into your wardrobe is with this Chelsea boot that feels both rugged and refined. The tiny faux pearls blend seamlessly into the print, so you might not even notice them at first, for an added kick in style.
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Sand Color Suede Ankle Boot
Alexa Suede Ankle Boots
Discard last season’s beat-up suede ankle boots for a fresh new pair. The light tan color and footwear silhouette make it a good everyday shoe you don’t have to try too hard to style.
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Lug Sole Ankle Boot
Cosmo 2.0 Chelsea Boot
The work boot is one of fall’s most sought-after shoes this season, so when you find a pair you love online, start punching in your credit card number. My pick is this chunky platform boot with a bit of a punk-rock attitude.
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Embellished Ankle Boot
Magnetic Calf Boot
These ankle boots feature everything, from glass studs to gold-rimmed embellishments, if you’re looking for a shoe that has some extra personality. They’re made in Italy and have a double padded leather insole for a comfortable, cushioned feel.
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Woven Ankle Boot
In The Loop Woven Boots
I’m a yes when it comes to woven footwear, which is why I gravitated towards this bootie. It comes in two colors, so if the mustard yellow isn’t for you, try the light grey. Wear socks if you wish, though I’d go without.
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Grid Pattern Ankle Boot
Ankara Green Bootie
You’ll be able to walk miles in this bootie; dr. Liza’s shoes are all equipped with a comprehensive orthotic insole, a shock-absorbing platform, and a rocker sole to alleviate metatarsal pressure to name a few. Sign me up for a pair.
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White Ankle Boot
Hitch Hiker Boots
For an edgier version of your white stiletto heel bootie, try these lace-up combat boots. It has thick studded soles and a Fenty-branded tongue just in case your friends ask where they can buy a pair.
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Snake Print Leather Ankle Boot
Sonni Booties in Luggage Leather
Now you don’t have to choose between wearing your snakeskin bootie or brown leather bootie—you can wear both. This low heel ankle boot pairs perfectly with your cropped boyfriend jeans.
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Sock Boot Ankle Boot
Tabi Faux Leather Sock Booties
For the ankle boot that will really draw some accolades, invest in Maison Margiela’s iconic “Tabi” booties. The split-toe design makes it unlike any other shoe you’ve ever worn.
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A Knit Boot
Kaylee Ankle Boot
This taupe-colored bootie has a knit upper that comfortably wraps around your ankles. The shoe is weather-resistant, so you can breathe a sigh of relief when you’re wearing them and there’s a light drizzle outside.
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