Sure, you probably have a few pairs of ankle boots in your collection by now, but why not add a few more? Exactly. After all, this is the one shoe silhouette that does the most work for you this time of year, so having a healthy assortment of the perfect pairs to work with every ensemble and occasion is worth it. But this doesn’t mean going out and dropping all your cash on brand-new styles (although if you want to, live your life). There’s actually a huge array of forward on-sale iterations out there upward of 60% off, starting at just $39. Keep scrolling to check out the prettiest ankle boots that are seriously discounted. But you better act fast; these won’t stick around for much longer.
Under $50
Old Navy
Faux-Suede Slim-Calf Ankle Boots
The faux suede makes these look way more expensive than they actually are.
Truffle Collection
Block Heel Ankle Boots
You can’t go wrong with brown block-heeled booties.
Express
Leopard Print Booties
If you haven’t tested out the leopard-print trend yet, now’s your chance.
ASOS
Realm Suede Ankle Boots
The studded detail brings a little something different to this classic silhouette.
$50 to $100
Halogen
Women's Halogen Bergen Boot
The white ankle boot trend isn’t going away anytime soon.
Sam Edelman
Winona Metallic Textured-Leather Ankle Boots
Ready to jump on the Western boot look? Here you go.
Sarto by Franco Sarto
Eames Booties
The burgundy hue feels incredibly luxe.
Steven Madden
Partial Booties
If you’re not quite ready to fully try Western boots like the above pair, these have similar details to dip a toe into that trend pool.
Fitflop
Uberknit Sock Boots
If Sporty Spice is more your style, we recommend these sleek sock boots. Don't forget to use the code WWW20 to get a 20% off discount.
$100 to $250
Nanushka
Clarence Leopard-Print Calf Hair Ankle Boots
Yet another reason to try the animal-print look.
Dorateymur
Han Textured-Leather Ankle Boots
This shape is especially unique.
Rag & Bone
Ellis Leather Ankle Boots
Yellow booties are so forward for the season.
LOQ
Lazaro Patent-leather Ankle Boots
Just imagine these with cropped jeans and a chunky knit—perfect for the weekends.
$250+
Loeffler Randall
Gema Boots
Make a statement in red.
Amina Muaddi
Lydia Reflective Stretch-Knit Sock Boots
These sock boots are made of a reflective material for an eye-catching look.
Rosetta Getty
Patent-Leather Ankle Boots
We’re seeing this curved heel silhouette more and more.
Ellery
Leather Ankle Boots
The shiny heel gives these beautiful boots a special twist.
Francesco Russo
Zebra-Appliquéd Leather Ankle Boots
While leopard-print is clearly a major trend, the zebra look is also all the rage.
3.1 Phillip Lim
Agatha Suede Ankle Boots
You’ll turn heads in an instant with these hot pink stunners.
Tibi
Dylan Patent-Leather Ankle Boots
Check all the trend boxes with these white Western boots.
Rejina Pyo
Marta Patent-Leather Ankle Boots
Kitten-heel booties are becoming one of the key silhouettes of the season.
Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.