This article was last updated on April 16, 2022
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Choosing between a classic piece and a trendy piece in regard to any clothing category is far from an easy decision. A wardrobe staple, while reliable, can often feel tired mid-season, but while that trend-driven item may have looked like a good idea in the fitting room at Zara, it might not be worth the investment if it’s only good for one season. The solution is all about the subtle merging of staple silhouettes and unexpected embellishments to get a little bit of both. And when it comes to the iconic black ankle boot, that means opting for new heel shapes and inventive designs.
These cool takes on an old relaible can make your go-to shoe feel a little bit fresher this fall. Because like it or not, bootie season is upon us — and if you’re ready to ward off the upcoming chill in style, these boots have you covered…or, well, at least your toes.
ASOS Rida Lace Back Ankle, $72, available at ASOS.
Proenza Schouler Lace Up Boot, $1,160, available at Proenza Schouler.
Rachel Cox Ankle Boots Gella RPL143, 447, available at W Concept.
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Whether you’re a leather or a suede gal, this boot has you covered. Find more trendy styles like this at T.J.Maxx.
T.J.Maxx Peep-toe Suede Bootie, shop more at tjmaxx.com.
& Other Stories Suede Lace Up Boots, $195, available at & Other Stories.
Stuart Weitzman The Stitchwork Boot, $585, available at Stuart Weitzman.
J.Crew Hadley Patent Leather Boots, $278, available at J.Crew.
Urban Outfitters Flame Platform Ankle Boot, $79, available at Urban Outfitters.
Dolce Vita Varra Booties, $170, available at Dolce Vita.
Coach Moto Bootie, $495, available at Coach.
Mango Zipped Leather Ankle Boots, $149.99, available at Mango.
Trademark Mira Mid Booties, $798, available at Shopbop.
M.Gemi The Corsa Moto, $448, available at M.Gemi.
Aska Goldie, $495, available at Aska.
Michael Michael Kors Andi Leather Ankle Boot, $245 $183.75, available at Michael Kors.
Zara High Heel Leather Ankle Boots with Colorful Stripes, $139, available at Zara.
Archive Shoes The Madison Boot, $298, available at Archive Shoes.
Kenneth Cole Alyssa Patent Leather Boot, $185, available at Kenneth Cole.
Nine West Justin Booties, $139, available at Nine West.
Alexander Wang Gabi Bootie with Rose Gold Metal Heel, $775, available at Alexander Wang.
By Far Becca Black Suede, $555.44, available at By Far.
Bershka Mid Heel Sock-Style Ankle Boots with Front Zip, $59.90, available at Bershka.
H&M Suede Kitten-heel Boots, $79.99, available at H&M.
3.1 Phillip Lim Hayett Pearl Stud Combat Boots, $750, available at Intermix.
Neous Boot in Black, $640, available at Need Supply Co.
Rachel Comey Lin, $449, available at Rachel Comey.
MM6 Maison Margiela Patent-trimmed Leather Ankle Boots, $685, available at Net-A-Porter.
Opening Ceremony Ryder Pearl Boots, $395, available at Opening Ceremony.
Loeffler Randall Isla Slim Ankle Bootie, $450, available at Loeffler Randall.
Acne Studios Saul Reverse Black, $690, available at Acne Studios.
See by Chloé Janis Suede Studded Strap Low Heel Booties, $425, available at Bloomingdale’s.
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