Whether you love walking everywhere, have a job that keeps you on your feet all day, or are just that person with sore feet who’s always looking for a place to sit, comfy shoes are a must. (Your feet deserve it!) But for the times you don’t necessarily feel like wearing some sneakers and prefer a dressier look without getting out your heels, there’s a perfect middle ground—a comfy pair of ankle boots.
Now when you hear the word “boots,” your mind might immediately jump to fall or winter. But, ankle boots are cut so low that most can actually be worn year-round. They’re one of the few shoes you can pair just as easily with jeans and a sweater for holiday parties as you can with a cute mini dress for summer rooftop cocktails.
Either way, the days of sore, tired feet are gone. Get a pair of essential black booties to wear with anything 365 days a year, then get some fun, leopard-printed boots to wear when you’re in the mood for a bold look. If you’re into hiking, you’ll definitely want a pair of waterproof hiking boots for your most comfortable outdoor adventures yet. There are even lots of cozy ankle boot options for wider feet, too.
From memory foam-padded Dr. Scholl’s boots to fur-lined Skechers and trendy Timberlands, these are the best comfortable ankle boots for every style, lifestyle, and budget in 2021.
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Collins Combat Boot
The lace-up detailing on these combat boots is super cute, and they provide some great ankle support, too. Lined with memory foam padding, they’re available in black and brown—at a price so low, you’ll want one of each to go with everything in your wardrobe.
Best Ankle Boots For The Value
Hope Clara Ankle Boots
If you’re looking for a pair of boots that’ll last you for a decade without breaking the bank, these Vionic boots are it. They’re weather-proof, have a microfiber footbed, and feature targeted support in the arches of your feet.
Best Investment Rain Boot
Harlow Chelsea Rain Boot
Living in a rainy city, or one with unpredictable weather? These rain boots are a great investment piece because they don’t look like typical rubber rain boots. The sleek exterior is totally waterproof, and the best part? They feature a slip-proof ridged bottom that’s made specifically to grip onto slippery streets.
Best Affordable Rain Boot
Rubber Non-Slip Booties
On a budget? No worries. These classic black rain boots feature a subtle embossed print that’s super cute. You may not love the rain, but putting these on before you brave the outdoors will definitely bring some pizazz to your outfit.
Best Versatile Ankle Boot
Platform Chelsea Boot
With a bit of a higher shaft, these are great if you want something that’s right in the middle of an ankle and knee-length boot. They’re trendy enough to wear out with a sexy dress but the removable lug sole makes them really stylish and functional, too.
Best Warm Weather Ankle Boot
Black Microfiber Suede Dakota Boot
These wedge booties look so cute nobody will know how comfortable you really are. The memory foam padding is made with cool-fit technology that’s designed to keep your feet dry while looking extra stylish.
Best Cold Weather Ankle Boot
Faux Fur-Lined Booties
Furry, cozy winter boots get a bad rep for being really heavy and hard to walk in, but these are made with a feather-light cushioning. They’re expertly designed with faux fur that’ll keep you warm while still being sweat-free—a must when you’re moving from being indoors around central heat to outside in the frigid cold.
Best Platform Ankle Boot
Womens Lug Sole Platform Ankle Boots Elastic Chunky Block Heel Non-Slip Combat Comfortable Chelsea Booties
Consider these the shoes you wear when you don’t actually feel like wearing shoes. The slip-on boots have a sock-like feel to them that feels really supportive around your ankles, and the trendy block heel is lightweight enough to walk in all day without feeling like you’re lugging around a heavy heel.
Best Animal Print Ankle Boot
Leopard Ankle Boot
Animal print makes every outfit more fun but that doesn’t always equate to comfort. These have a super subtle heel that’s just enough to provide some sole support, and a padded footbed to keep you looking and feeling amazing for hours on your feet.
Best Hiking Ankle Boot
Waterproof Hiking Boot
Whether you’re a regular on the trails, love camping, or just enjoy taking frequent nature-centric trips, it’s essential to have a good pair of comfortable hiking boots. These are made with thick sole cushioning, a waterproof lining, and slip-proof rubber heels for ultimate comfort and safety.
Best Trendy Ankle Boots
Prema Faux Leather Combat Boots
Add these stylish combat boots to any outfit, and they’ll give you serious cool girl vibes. But they don’t just look good—they feel good. The lace-up feature provides some great ankle support, too.
Best Ankle Boots For Snow
Waterproof Insulated Sneaker Boot
Lined with fleece and an outer coated canvas, these boots are like the cozy house slippers you can actually wear outdoors. They’re waterproof and have a slip-proof rubber sole that make them perfect for snowy days.
Water Resistant Hiking Boot
Timberland’s are a classic, and there’s a reason people are obsessed with them. They’re the most stylish hiking boots around, but they also feel like a dream. Between the water-resistant finish, lugged sole, and comfort-cushioned footbed, these will be a standby forever—whether you actually plan on hiking in them or just want to wear them as a trendy, all-weather staple in your wardrobe.
Best At-Home Boots
Espadrille Faux Fur-Lined Bootie
No movie night or self-care night in is complete without these cozy sherpa booties. The faux fur lining literally cradle your feet, and the thick platform means you can even throw them on for a quick grocery store run, too.
Best Classic Boot
Mini Classic Boot
You know these. If you don’t already own a pair, you should know that they are absolutely worth the hype. The ultra plush shearling is made to be sweat-wicking, so you can even wear them without socks to easily slip in and out of them all winter.
Best Vegan Leather Ankle Boots
All Vegan Leather Bootie
There’s nothing more chic than some patent leather booties. Add them to a simple jeans and t-shirt outfit to class up the look, or wear them with your favorite LBD year-round for a sexy night out.
Best Ankle Boots For Wide Feet
Wide Ankle Boot
For those with wider feet, nothing is more uncomfortable than a super structured, narrow shoe. Not only do these fashionable block heel booties feature a wider base, they have a stretchy fabric that’ll form fit to the unique contours of your foot.
Best Sneaker-esque Ankle Boots
Not ready to let go of your sneakers, but want something that’ll cover up your ankles in fall and winter? Consider this the light turtleneck of shoes. The breathable fabric means you could get away with wearing these in the summertime, too.
Best Luxury Boots
Nail Pointed Toe Bootie
These are definitely a luxury buy you’ll want to save up for, gift to your best friend, or ask for on your birthday. The high-end brand, Off-White, is all about taking classics and adding fun spins to them, so know that you’re getting a totally unique item when you get a pair of these.
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