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—including a fabulous floral pair from Ree's line! So, whether you throw them on with jeans or a dress, you'll be feeling comfy and looking cute in any of these 13 best options.

The Pioneer Woman Embroidered Western Ankle Boot

A stacked heel, stitching accents, and the most fabulous floral embroidery gives these Western booties from Ree's line the most country chic flair! We're especially loving the pink and red pops of color atop a sleek brown. They're made of supple vegan leather with a 2.5-inch heel that gives just the right amount of height without discomfort—especially thanks to the built-in lightly padded sock. An inside zipper and side tabs even ensure that they're easy to get on and off.

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. Specifically, the lightweight Chelsea shoe is made with insole technology that focuses on all-day cushioning and shock absorption that will help to reduce foot pressure and fatigue. They'll also got a flexible construction that will move with your feet. Note: The manufacture recommends sizing up a half size.

Lucky Brand Basel Booties

Lucky has been making this bootie for many seasons, and the classic shape never goes out of style. It has a round toe design and a stacked block heel that measures just 1.5 inches. As for comfort, your feet will definitely enjoy the lightly cushioned footbed. Oh! And those dual side zip closures serve as both a stylish accent and an easy way to slip the boot on and off. 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 and decorative buckle of these booties is a super-soft memory foam sole that will cradle and cushion your foot through the day. It's extra breathable and flexible, too. And since the block heel is the perfect height of 1.25 inches, you don't have to worry about getting sore—it's also built to offer balance and stability.

Perforated Microsuede Ankle Boots

A geometric perforated design and deep cut-out make these micro-suede booties anything but basic. Not only is the cut-out stylish, but paired with the back tab, it makes for an easy, slip-on fit, too. They also feature a one-inch stacked heel combined with Dr. Scholl's signature memory foam insoles for all-day anatomical cushioning and support as well as a lightweight, flexible construction that moves with your feet.

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—and it's all because of that snip toe profile and colorful geometric textile detailing. Since they have a lightweight design with a flexible rubber outsole and cushioned insole, they'll feel good, too. The zipper closure even makes for easy on and off.

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. Here's what makes them so great: along with the water-resistant material that will keep your feet comfy and dry, they've got a non-slip rubber sole for extra stability. Though they're rain boots, they're designed to be lightweight and have a roomy toe area with a super comfy (removable) EVA foam insole. Bonus: fabric edged finish and fabric lining also reduces friction around the ankles.

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 cold-weather activities. That's in addition to the cool contrast laces and two-tone outsole. After you lace them up the first time, they'll be easy to get on and off thanks to the inside zipper. Despite their heavy-duty look, they're actually very lightweight with a flexible bottom that moves as you do—but there's still a treaded outsole for great grip. The insole is padded as well!

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. The booties are wrapped in soft, hand-laid rubber for 100% waterproof protection. On top of that, molded memory-foam footbeds mean you'll stay comfy. They also feature an odor and moisture management insert and durable outsole for plenty of traction.

LifeStride Women's Jezebel Ankle Boots

The bubble buckle straps dress up any outfit that you pair with these adorable prairie booties. But don't let those accents unnerve you, as there's still a side zip to get the boot on and off. You'll also be thankful for the next level heel-to-toe comfort that comes with LifeStride's three-part comfort system technology. Cushy and breathable foam cradles your foot while arch and heel support allows for balance and stability. An ultra-flexible outsole also adds ease to every step.

Everlane The Rain Boots

This dependable rain boot is good for rain, snow, and sun, thanks to their thick slip-resistant tread and cushy insoles. And no matter the occasion, those stretch side panels and pull tabs make it easy to slide on and go while easy-to-clean rubber will always look good as new. Keep in mind that the flexible style was designed with thick winter socks in mind, so if you're planning to wear thinner socks, you might want to size down by a half size.

Vintage Worn Western Ankle Boots

You'd never know these boots are faux suede—they look like the real deal. And how stylish is that slightly slouchy design? Reviewers also rave that they're super comfortable and not slippery. That's no surprise with the easy-to-wear stacked heel, round toe, and lightly cushioned fabric insole that lends itself to long hours of wear.

Ariat Wexford H2O

These pretty leather shoes are actually sturdy rain boots in disguise. They're made of a breathable and durable 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. The elastic panels on each side make for a stretchy yet secure fit that's only made better by the convenient pull-tab on the back.

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