Womens/Shoes/Boots/Ankle Booties & Tall Boots

Top 10 Pointed Toe Booties

The Top 10 Pointed Toe Booties To Wear Right Now

The Top 10 Pointed Toe Booties To Wear Right Now

Boot season is officially on, which means there's no better time to flex your fashionable new footwear than now! Since we're not quite in the season for breaking out the heavy-duty boot styles that require long socks just yet, it's the ankle bootie's time to shine. While we love all varieties of the ankle boot, today we're focusing on one particular fan-favorite style: the pointed toe. Sure, the rounded toe boots have their appeal, but a pointed toe bootie is the key to effortlessly slaying any autumn ensemble with slip-on or zip-up ease. We’ve used our data-driven algorithm factoring in best-selling buzz, editorial selections, and real user reviews to create a vetted list of the best pointed toe booties on the web. Not only are these top-rate pointed toe booties made with updated details that elevate the drama, but they also feature chunky heels and high-quality material to ensure each pair is made for walkin'. Find your perfect pair with selections from beloved brands including Sam Edelman, Blondo, Steve Madden, Matisse, and more. So, are ya ready, ladies? Start shopping! Opening image: everlane.com

Love our 10 Best Pointed Toe Booties? Check out our 10 Best Ankle Boots next!

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October 15, 2019

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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

Blondo Elvina Waterproof Bootie
Rank & Style Approved


Blondo Elvina Waterproof Bootie

LOVED FOR: In addition to featuring a buzz-worthy pattern for the fall, these chunky heel booties are waterproof and can stand up to the elements of the season. 

STYLE WITH: Rock a lightweight turtleneck and a slimming pair of black skinny jeans for an edgy look. 

Chinese Laundry Finn Bootie

USERS SAID: "I absolutely love these boots!! Just the right height heel and the pointy toe is so trendy. I get tons of compliments on them and ordered the same pair in black."

HELPFUL TIP: These booties run small. Order one half size up for the best fit. 

Marc Fisher Yale Chelsea Boot

BEST FOR: Slip into these pointy-toe Chelsea booties to nail an everyday slay.

LOVED FOR: The pull-on style, modern silhouette, and high-quality material options

Mango Leather Cowboy Ankle Boots

WHY YOU NEED THEM: These Mango ankle booties borrow from the timeless cowboy boot silhouette while also featuring minimal details to create an updated approach to your typical Western-inspired footwear. Wear them with just about anything denim for an instantly chic touch. 

WHERE TO WEAR: Out to girl's night or during a fall music festival 

Steve Madden Jillian Bootie

LOVED FOR: The block heel, pointed toe, and supple leather 

USERS SAID: "Everyone is asking where I got my boots. I got them in the tan suede and love them. Perfect fit! I wore them with my jeans and also with a cute dress. This is a must have for this year."

Matisse Caty Boot

WHAT IT DOES: Designed with cowboy boot-inspired style and a tall vamp, these Matisse booties create a slimming effect on the ankles while complementing any denim or pant fit. 

HELPFUL TIP: These chunky heel booties fit true to size. 

Sam Edelman Winona Bootie

USERS SAID: "I have been searching for just the right style of faux snake skin boots and these are perfect. Sam Edelman has just been knocking it out of the park. Highly recommend!!" 

STYLE WITH: Go for the All-American classic combination when you add a pair of Levi's jeans

Jeffrey Campbell Siren Bootie

BEST FOR: These saucy stacked heel booties are ideal for turning heads on a night out. 

LOVED FOR: The pointed-toe, comfortable fit, and dramatic silhouette

Everlane The Boss Boot

WHY YOU NEED IT: In addition to being super walkable for all your fall and winter adventures, these booties are made from premium Tuscan leather and feature edgy details like a side zipper and a sharply pointed toe. 

FUN FACT: These boots fit true to size and were handcrafted in Italy. 

Sam Edelman Hilty Bootie

USERS SAID: "LOVE LOVE LOVE!! These snakeskin print booties are gorgeous and comfy. First day I was able to wear them for hours. LOVE!!!!!! Get them...I want more!"

HELPFUL TIP: This bootie runs small and purchasing the next size up is recommended for the best fit.

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