Womens/Shoes/Boots/Ankle Booties & Tall Boots

Top 10 Heeled Boots

If You Only Make One Shoe Purchase This Fall, Let It Be A Pair Of These Classic Boots

If You Only Make One Shoe Purchase This Fall, Let It Be A Pair Of These Classic Boots

Our Top 10 Lists help shoppers quickly and easily find what they need. Using an intense review and approval process (which you can learn more about here), we break down the best styles according to what consumers most commonly search for and want.

Every fall season brings with it an abundance of boot trends to obsess over, and this one is no different. Right now, retailers are brimming with chunky lug soles, edgy lace-ups, sleek knee-highs, and cowboy boots galore. But there's one boot style—no matter the ever-changing trend cycle—that will always be a timeless choice. Enter: the good ol' classic heeled boot.

You know the one—it's the kind of boot with a sensible, usually stacked heel you can walk miles in, and you can pair it with everything from jeans to dresses to work pants. Whether you opt for sophisticated black leather and pointed toes or chic suede with covered block heels, this staple shoe style will never steer you wrong.

With that in mind, we rounded up a list of the 10 best heeled boots you can buy right now, all of which will last you for seasons to come. From $120 to $450, there's a top-rated heeled boot on this list to suit every budget and style.

How We Found The Best Heeled Boots

To round up this list, we turned to the help of our unbiased algorithm. This proprietary tool finds and ranks the best products on the web by factoring in best-seller lists, editor recommendations, rave reviews, and more. Ahead, shop the 10 pairs that made the cut and invest in your new go-to.

Next up, check out the 10 Best Ankle BootsOpening image: madewell.com

Jump To Products

November 1, 2021

FacebookPinterest logoTwitter logoEmail icon

Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.

The Rankings

Marc Fisher LTD. Alva Bootie
Rank & Style Approved


Marc Fisher LTD. Alva Bootie

WHY IT MADE THE LIST: We've officially found your new LBB (little black boot). With sleek black leather, a pointed toe, and a bold block heel, you'll wear these under-$200 beauties for years to come.

USER REVIEW: "Amazingly comfortable bootie! I wore this bootie with no break-in time at all for a whole day of sightseeing activities, and my fitness tracker said I had walked over two miles in the shoes by the end of the day."

Sam Edelman Codie Square Toe Bootie

WHO IT'S FOR: If you want a boot that stands out without going overboard, look no further. With a sophisticated square toe and all-over suede, these boots make a subtle statement.

WHERE TO WEAR: The all-black vibe makes these boots ideal for dressier looks. We'd pair them with pants and dresses for workdays and date nights.

Marc Fisher LTD. Jarli High Heel Booties

STYLE WITH: The pointed toe, walkable 2.5-inch block heel, and sleek black leather make these booties a no-brainer for all your oversized sweater ensembles.

ADDITIONAL THINGS TO KNOW: These booties also come in ivory (we see you, winter brides), tan, and a gorgeous grey suede.

Madewell The Regan Boot

WHY IT MADE THE LIST: It doesn't get much more classic than these. Complete with gorgeous leather, a pull-on silhouette, and walkable block heels, they're the kind of booties you'll wear everywhere and with everything. Bonus: Madewell added an extra layer of its signature padding to make them extra comfortable.

ADDITIONAL THINGS TO KNOW: If you're between sizes or want to wear these with thicker socks, order a half size up. Otherwise, stick with your normal size.

Dolce Vita Caster H2O Booties

WHO IT'S FOR: If you want something on the trendier side, Dolce Vita has you covered. With a '70s inspired silhouette and clog-style sole, these statement-makers provide a significant height boost without the foot pain and add instant glam to any look.

ADDITIONAL THINGS TO KNOW: The Caster Bootie is waterproof, so it's perfect for rainy fall and winter days.

Rag & Bone Rover Booties

WHY IT MADE THE LIST: The Rover Bootie hits all the sweet spots—it has a just-right heel height that's not too tall and not too short, and the camel suede color will pair with everything in your closet.
USER REVIEW: "This boot was an instant hit when it arrived in the mail. The suede is so soft and high quality. The structure is also nice with a comfortable fit and soft interior. This boot is so beautiful and well made!"

Madewell The Laura Chelsea Boot In Leather

WHY IT MADE THE LIST: These stunning boots might just be the boots to end all other boots. Available in black and brown, they have a slightly taller shaft, sleek leather, and a sexy high heel that make them instant classics. To top it all off, they're also made with Madewell's MWL Cloudlift Lite padding for a super cushy feel with every step.

ADDITIONAL THINGS TO KNOW: This pair is made from ISA LITE (Low Impact To the Environment) leather that uses less energy and water than the standard tanning process.

Loeffler Randall Isla Booties

WHY IT MADE THE LIST: These are basically those go-to ankle boots you wear with everything, but they come with elevated touches that kick them up a notch—think gorgeous suede, a dramatic pointed toe, and an oversized wrap heel.

STYLE WITH: These are dying to be paired with a billowy fall midi dress.

Jeffrey Campbell Siren Pointed Toe Bootie

WHO IT'S FOR: If you're here for the height boost, look no further. Clocking in at 3.5 inches, these sleek booties are the highest on the list but are still super walkable.

USER REVIEW: "These boots are my go-to staple year after year. They are sleek and chic while being the most comfortable boots I own. Also, the fabric seems weatherproof, so these boots can endure! Love them!"

Everlane The Glove Boot

Overall Score



Everlane The Glove Boot


1377 User Reviews


Best Seller


Industry Recognition


Social Buzz

About Our Scoring System

In order for any product to be featured on Rank & Style, it must first meet the requirements set by our algorithm—a vetting process that allocates points based on consumer and industry data to score and rank products within a given category.

Learn More

Best Knit Ankle Boots

WHAT TO LOVE: If you live in a warmer climate, go with these fan-favorite Everlane booties. Made with stretchy knit fabric, they're extra breezy and will work well into the spring and summer months, too.

MORE DETAILS: These boots are made from renewed plastic bottles—nine, to be exact.

More Colors

More Colors

View All Top 10 Lists
Arrow white

The Latest

Image credits: oldnavy


Top 10 Plus Size T-Shirts

T-Shirt Season Is Back—Here Are The 10 Styles Plus Size Women Are Loving Most

View All Womens

From Our Partners

Image credits: jane iredale

Jane Iredale

Meet TikTok's NEW favorite eye shadow stick, ColorLuxe by Jane Iredale.

Shop Now

Arrow white

Straight-to-the-point emails to make finding what you love even easier.