The 20 Best Ankle Boots We're Buying in 2019

last updated 14 August 2019

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I might not know a lot, but what I do know is a good ankle boot when I see one. To preface, no, I am not actually buying all 20 of the ankle boots you're about to see right this instant, but I will own them before the end of the year, and that's a fact. After wearing and tearing through too many boots to count, I can say with confidence that I know when a pair of shoes is worth investing in and when they aren't, and the 20 I've selected here are worth every penny.

This year, whether I'm in need of a solid everyday pair of black ankle boots or searching for that special pair that will take my going-out look to the next level, I am vowing to use this gorgeous (if I do say so myself) list to guide all of my 2019 ankle-boot purchases. Ready to see which chic-to-death shoes I'm craving this year?

Rejina Pyo

Red Annie 25 Curved Heel Suede Boots

Red boots can be worn in any season and pretty much with every outfit.

Zara

Leather Heeled Cowboy Ankle Boots

My black cowboy boots are all kinds of scuffed up, so a replacement pair is necessary stat.

Ellery

Stretch Cowboy Boot

I plan on wearing these with jeans, dresses, and everything in between.

Topshop

Howdie High Ankle Boots

Quite possibly the chicest white ankle boots I've ever seen.

Tibi

Grant Booties

Tibi boots are the designer boots I'll invest in till I die.

Bershka

Leather Track Sole Ankle Boots

For anyone living in New York, there's no denying the power of a sturdy pair of hiking boots to wear rain or shine.

Labucq

Jules Mineral Python

Snakeskin boots with a bit of wearable flair thanks to the gray and green tone.

Dr. Martens

Jadon 8 Eye Boots

I have had these in white for over a year, and you can tell. It's time for me to finally invest in the black pair.

Malone Souliers

Claudia Mesh and Leather Ankle Boots

Cinderella would definitely approve of these.

Dorateymur

Groupie Knot Boots

Knotted to perfection.

Gia Couture

Python Print Ankle Boots

My co-worker owns these, and I've tried to restrict myself from buying a pair, but clearly, I have no willpower.

Proenza Schouler

Canvas Ankle Boots

Hiking boots mixed with sneakers is my new aesthetic for 2019.

Rag & Bone

Beha Booties

These black boots are perfect for everyday outfits and going-out looks.

Ganni

Low Texas Boots

I own a black and a white version of these, but obviously, my lack of willpower is getting the best of me yet again.

By Far

Este Croc-Effect Leather Ankle Boots

I never knew I needed a pair of flat boots so badly.

Alexander Wang

Spencer Leopard-Print Calf Hair Chelsea Boots

Weather-proof and insanely cool all in one.

& Other Stories

Cowboy Sock Boots

Okay, just one more pair of cowboy boots—I promise.

Paris Texas

Ankle Boot

This is a shoe brand you should definitely keep your eye on this year.

Yeezy

Thick Soled Desert Boots

The sneaker–hiking boot duo strikes again.

Freda Salvador

Charm Boot

Last but not least, the everyday black ankle boots I've been telling everyone about.

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Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over nine years, where she started as an associate editor and has since worked her way up. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. Here, she leads and manages Who What Wear's editorial team and oversees all editorial content. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many celebrity cover shoots, including big names like Kaia Gerber, Normani, and Sabrina Carpenter. She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her style has been featured on sites such as Vogue, Harpers Bazaar, and Elle.