Unisa Ressie Bootie
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.
Marc Fisher Tune Pointy Toe Fringe Dress Bootie
Zara Contrast Buckle Ankle Boots
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.
Banana Republic Canton Boot
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.
Old Navy Ankle Strap Boot
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.
Coconuts by Matisse Camilia Suede Bootie
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.
Nine West Tanesha Pointy Toe Booties
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.