The 9 Best Booties For Dresses

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SIBIU, ROMANIA - JULY 24: Isabela Francesca wears a white felt / wool hat, white pearls pendant earr...
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Ankle boots are one of the few pairs of shoes with year-round mileage: They don’t cover much more real estate than a good pair of sneakers and are great for anchoring outfits while providing a little edge. They’re especially ideal for any outfit involving a skirt, because the best booties for dresses will work just as well with a floral dress and bare legs as they do with a pair of tights and a cable knit midi. Whether you prefer a chunky lug sole that brings downtown attitude or a TikTok-approved cowboy boot, the right bootie can pull an entire outfit together.

Of course, you always need to have a few good neutral-hued boots in rotation, but it’s also nice to have at least one pair of booties that can inject some personality into your wardrobe staples. If you’re going bare-legged, an ankle boot close to your skin tone can be worn with virtually any dress and creates an uninterrupted line from hem to heel. In the fall and winter, I’m partial to boots that match your leggings or tights whether that’s black, taupe, or burgundy for a similar effect with cold-weather coverage. Feel free to disregard this advice if you want to make a statement — color, pattern, and contrast will draw the eye to your shoes when you want to spotlight their style. Plus, optimistic color choices feel particularly of the moment, not to mention, ultra-creative when juxtaposed against patterned pieces.

Most of the options here come with a closed toe for that year-round versatility, but I’ve also included a fashionable pair of open-toe booties when you want the attitude of boots in a summery fit. No matter when or where you plan to rock this style, kick up your heels in any of these nine stylish ankle boots.


These Classic Boots With A Midi Heel That Come In So Many Colors

Timeless yet modern, with a clean shape and a bit of lift (the heel height is about 2 inches), these ankle boots are just right for so many reasons. They’re offered in multiple iterations of vegan leather and plenty of colors, whether you want something that will create a streamlined look with bare legs or statement shades like blue or white (or black for winter wear). The block heel adds polish, and a cushioned footbed keeps things walkable. “They have quickly become a staple in my wardrobe,” one shopper wrote. “After a few months of regular wear (including nights out) they show no sign of wear, stains, anything.” For a similar style with a little more elevation, try these block heel ankle boots with a 3.5-inch heel.

  • Available colors: 13
  • Available sizes: 5.5 — 11


Some Chunky Platform Boots For Peak Y2K Style

Blending a Chelsea boot with punky combat energy, these platform ankle boots channel the early ‘00s trend that is cropping up everywhere. They’re easy to slip on thanks to a heel tab and wide elastic gore, and the soft, padded insole belies their tough-as-nails tread. The heel maxes out at just over 2 inches but feels sneaker-flat thanks to a thick lug sole that’s surprisingly bouncy and light, according to reviews. “These are super cute! True to size and such a hot look this year,” one shopper gushed, noting that “designers showed these chunky boots all over the runway for Paris and Milan Fashion Week. [...]They're comfy and I'll get a lot of wear out of them.”

For a pair of lug sole boots with a bit more bling, also consider the Steven Madden Amulet boots.

  • Available colors: 5
  • Available sizes: 5 — 11


Some Slouchy Cowboy Booties With A Cult Following

Boasting more than 7,500 Amazon ratings, these slouchy cowboy boots could just be the most versatile player in your footwear line-up. Available in a nice range of colors, the faux leather boots feature a 2.5-inch heel, a padded lining for cushioning, and a durable sole that promises to keep you on your feet. Plus, the tabs on each side make pulling these on a breeze. One fan raved: “I wore them everyday at work last week with very different outfits and they looked great with each of them.”

If you’re looking for an even more Western feel, consider these popular cowboy boots, too.

  • Available colors: 9
  • Available sizes: 6 — 11


A Pair Of Truly Flat Ankle Boots For Running Around All Day

If you’re in no mood for a heel, these flat ankle booties will keep you on terra firma. The heel is just a few millimeters thick and there’s a cushioned layer inside for comfortable wear — plus, there’s a hidden zipper inside the ankle and a dedicated heel tab for easy on or off. The TPR sole promises to be light yet sturdy with a layer of rubber on the bottom for waterproof grip. Choose from options in faux leather and suede with a subtle heel accent in quilting (or leopard if you’re feeling spicy). These booties, incidentally, are much beloved by people with foot issues, as they have essentially zero drop. “Love these boots! It is hard to find flat boots, especially ones that are as stylish as these with the cute quilting & zipper. The boots have a roomy toe box making them very comfortable. Have already done a couple of ‘shop to you drop days’ in these boots and my feet felt great,” a fan raved.

  • Available colors: 5
  • Available sizes: 6 —10


A Pair Of Square-Toe Booties That Come In Statement Shades

These boots are made for making an entrance and practically work the room for you. This sleek faux leather style comes with a square toe and block heel for an eye-catching yet relatively versatile style, and you’ll also find options in hot pink and patent leather that really turn it up a notch. The just under 3-inch heel provides height while still feeling eminently wearable, but a rubber sole gives you some added grip. “These boots are so perfect! Super cute, [comfortable] and fits perfectly. I absolutely love them!!!” one shopper gushed.

  • Available colors: 7
  • Available sizes: 4 — 15


A Breezy Pair Of Peep-Toe Booties

Light and airy but still relatively covered, these open-toe ankle boots are a nice warm-weather spin on the bootie. They have decorative buckle straps for a bit of fun hardware and a zip-up back so they’re easy to slip into. Some reviewers noted that they ran slightly large, especially through the ankle, which wasn’t necessarily a bad thing. They come in light and dark neutrals, but you might not be able to resist this rich burgundy, too, which is still nice and subtle but with a little bit more pop. “My favorite every day pair of shoes. They are sooooo comfortable yet make you look amazing and put together,” a shopper raved.

  • Available colors: 4
  • Available sizes: 5 — 11


The Neutral Patterned Ankle Boots That Go With *Everything*

These animal print ankle boots are cut low on the foot with V-shaped notches on either side for a contemporary shape. The negative space gives you extra leeway to wiggle them on, and a good heel tab on the back is there to help out. The heel is just 2 inches high for staying out all day and well into the night. They come in sophisticated natural palettes from calf hair leopard to snakeskin, plus chic taupe (with a python heel cap) and embossed white — all great, versatile options that are classics in their own right with that extra bit of character. “Love these booties!! Comfortable and stylish...They’re my go-to neutral shoe,” a fan praised. Several shoppers noted they ran a half-size large, so take that into account when you order.

  • Available colors: 4
  • Available sizes: 6 — 10


A Wedge Chukka Boot With Extra Stability

These lace-up wedge boots are a casually stylish option that provide solid footing with all the height of a heeled boot. The lace-up front gives you some leeway for sizing adjustments (or really thick socks) along with a secure fit. Their wedge heel measures 2.75 inches with a soft padded insert for all-day comfort, and the TPR sole is lined with rubber to be lightweight and waterproof. Score them in imitation suede or faux leather with a nice patina that looks surprisingly real for the price. “I own like 6 pairs of these booties in several colors and still want more! I wear them almost every day. They’re casual but you can also dress them up! The price is so great considering the impressive quality of these. Not to mention I can wear them all day at work and my feet never hurt,” a reviewer remarked.

If you want something dressier and are willing to spring for a steeper heel, look into these chic stiletto ankle boots from a different brand.

  • Available colors: 14
  • Available sizes: 5 — 12


These Sleek Brushed Leather Ankle Boots With Western Details

These ankle boots have Western-inspired lines with a clean cut through the vamp to keep them versatile without losing their frontier style. The leather is lined in fabric for soft breathability and there’s extra padding in the footbed, with an ankle zipper and surprisingly pretty heel tab to help pull them on while maintaining a streamlined shape. “Amazing. Buy these. They're so comfy that I could wear them all day. They are well structured and the material feels expensive (as it should!)” one reviewer reported. “These are one of those staple guys that you'll have in your closet forever. And these boots go with everything!” As far as Western boots go, they come in an excellent range of rich neutral tanned leathers including the ever-popular snakeskin.

To save some cash, these Western booties from The Drop have a similarly elevated look: a little less expensive with a little more cowboy stitching.

  • Available colors: 6
  • Available sizes: 5 — 12 (regular and wide)