These Cute Ankle Boots Are Comfortable Enough to Wear All Day

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In the wise words of Ree Drummond, "A good pair of boots needs some breaking in." And life on the ranch requires owning quite a few pairs of boots that will get worn in fast: muck boots for garden chores, cowboy boots for work and riding, and hiking boots for the occasional trek. But a pair of the most comfortable ankle boots for every errand in between should be ready to go right out of the box.

When shopping for a new pair of cute boots, there are few things to consider: The most comfortable ankle shoes will have a sturdy sole, a roomy-enough toe box, and ideally, a padded footbed. If it's a heeled ankle boot, the heel should feel substantial and easy to walk in. Of course, not all pairs are created equal. That's why we've made this list for your convenience!

Shorter boots have picked up in popularity in the last few years, and now there are tons of different looks and materials, including the ever-popular Chelsea boots for women, you can choose from to fit your style. Keep yourself bundled up and cozy in rainy or cold weather with a pair of cute rain boots or the warmest snow boots. We've even chosen a variety of materials and colors to fill your closet, too. So, flip through this gallery to see 20 of the cutest and most comfortable options. They're all made for walking! Just pop open the box and get going.

Dr. Scholl's Teammate Ankle Boots

If you're just dipping your toes (pun intended) into the ankle boot game, these are a great place to start. They come in several neutral colors and they're made by Dr. Scholl's, so you know they're comfy.

The Pioneer Woman Women’s Embroidered Western Ankle Boot

Lucky Brand Basel Booties

Lucky has been making this bootie for many seasons, and the classic shape never goes out of style. Choose from more than two dozen different colors and materials.

LifeStride Adriana Ankle Booties

You don't need to sacrifice style for support: Hidden underneath the pretty braided leather of these booties is a super-soft memory foam sole.

Perforated Microsuede Ankle Boots

A perforated design and deep cut-out make these microsuede booties anything but basic. They also feature Dr. Scholl's signature memory foam insoles for all-day comfort.

Roper Sedona Western Boots

These boots are perfect for when you want to add a little wild western flair to your look without going full cowgirl.

Asgard Short Rain Boots

Thanks to their always-cool Chelsea style, you can get away with wearing these #1 bestselling sleek rain booties on both rainy and sunny days.

Cliffs by White Mountain Duena Hiking Boots

A sweater ankle trim and faux shearling cuff make these off-white hiking boots the perfect choice for all of your winter activities.

Muck Originals Ankle Boots

These basic, tough-wearing boots are Ree's favorite brand of work boot (she used to buy the kids a new pair every year!). They're designed for work but they're also great for keeping your toes warm and dry when running errands in bad weather.

LifeStride Women's Jezebel Ankle Boots

A plush layer of memory foam cradles your foot in this adorable prairie bootie. The bubble buckle straps dress up any outfit!

Everlane The Rain Boots

This dependable rain boot is good for rain, snow, and sun thanks to their thick tread and cushy insoles. They also come in four neutral colors: black, green, toffee, and this stone shade.

Vintage Worn Western Ankle Boots

You'd never know these boots are faux suede—they look like the real deal. Reviewers rave that they're super comfortable, too.

Ariat Wexford H2O

These pretty leather shoes are actually sturdy rain boots in disguise. They're made of a breathable waterproof material on the outside and feature a comfortable elegant plaid lining with built-in support on the inside to provide warm and dry all-day comfort.

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