Kick off the cool-weather season with casual, yet chic boots that instantly add style points to any outfit. 

By Rebecca Daly
September 29, 2016
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
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One of this year’s biggest boot trends—a stretchy, sock-like top—also happens to be one of the most comfortable, with no stiff material to rub or chafe. Available in four colors. To buy: $109, dsw.com.
dsw.com
dsw.com

1

One of this year’s biggest boot trends—a stretchy, sock-like top—also happens to be one of the most comfortable, with no stiff material to rub or chafe. Available in four colors. 

To buy: $109, dsw.com.

marcfisherfootwear.com

2

A little bit country, a little bit rock and roll, this fringed pair looks best with something completely unexpected, like a feminine skirt or a long, flowy dress. Also available in black.

To buy: $139, marcfisherfootwear.com.

zara.com

3

This sleek, equestrian-inspired style is just what your weekend wardrobe has been waiting for. The oversized buckle adds just enough detail to make any jeans-and-sweater combo feel pulled together.

To buy: $50, zara.com.

bananarepublic.com

4

Look to newer neutrals to keep your fall ensembles feeling fresh. This olive shade of green feels a little more surprising than customary tan, but pairs just as easily with every color palette. Also available in nutmeg and black.

To buy: $178, bananarepublic.com.

oldnavy.com

5

Tried, true, and absolutely classic, a simple, flat, black ankle boot is a solid foundation for any cool-weather wardrobe. Also available in brown.

To buy: $40, oldnavy.com.

nordstrom.com

6

In pretty, go-with-everything grey and a manageable stacked heel, you’ll find yourself reaching for these booties to finish off endless outfits. Also available in black and tan.

To buy: $90, nordstrom.com.

ninewest.com

7

The MVP of the ankle boot world, heeled booties in black leather work at the office, at cocktail hour, and everywhere in between (not to mention with nearly anything in your closet).

To buy: $129, ninewest.com.

Need a little outfit inspiration for your new kicks? Read our ankle boot dos and don’ts here.