23 Ankle Boots to Buy Now and Wear Forever

Add a bit of flower power into your fall boot arsenal with these '90s-inspired Dr. Martens.

The minimalist white ankle boot dominated the fashion scene last season. We foresee the same trend taking over this Fall.

These sleek sheepskin-lined ankle boots will  take on puddles and wet fall leaves with ease.

Slip into these stretch knit ankle boots that will look equally polished with a dress or ankle-cropped jeans.

You don't have to sacrifice practicality or style. These waterproof ankle boots will look smart while combatting the elements.

Add a black-tie spin to your everyday ensemble with these patent-leather, square-toe-boots that take inspiration from formal wear.

Fall camping trips just got cuter with these contrast sole ankle boots in a poppy red hue.

A soft merino wool lining will keep your feet extra cozy, while a rubber sole deems these slipper-esque shoes safe for outdoor wear.

Trade out your worn-in suedes for this rugged, yet refined pair. Take care of them correctly, and you'll have them for years.

Take a closer look at these tough-looking boots and you'll notice sweet details like feminine gold eyelet detailing.

A studded sole infuses edge into these croc-embossed, rubber sole ankle boots.

Say hello to your new, very versatile. everyday ankle boot. 

Not all ankle boots are made equal, case in point: these fringe-faced ankle boots that come decorated with statement gold hardware.

These chunky-heeled combat boots are the perfect pairing for your fall floral dresses.

Heavy-duty enough for hiking, these snake print ankle boots will also look right at home on city streets.

These lug-sole boots are the perfect companion to an autumnal wardrobe brimming with fabrics like corduroy and tweed.

Invest in these for fall, and you're sure to wear them on repeat throughout the winter season.

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. 

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. 

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. 

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. 

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.

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.