The Ultimate Guide to Ankle Boots

The Vault Files

A new season means a new wardrobe, and the easiest way to transition your summer apparel into fall is to update your footwear and accessories. Once the temperatures start cooling down, then you can start thinking about jackets, coats and chunky knits. When it comes to transitional footwear, ankle boots are my favorite shoe style to ease into fall dressing while the temperatures still allow for shorts, skirts and dresses. They also pair well with just any look, and their versatility is what makes them a wardrobe staple. They have become such an essential that there are countless variations, twists and takes, making it easy to satisfy a wide range of style and budget needs.

To help you kick some pep in your step with a new pair of ankle boots here are 30 great pairs at various price points.

The Vault Files

The Pointy-Toe Bootie

This sleek and sophisticated style elongates the leg and instantly adds an instant cool-girl vibe to any outfit.

1. Old Navy Faux-Leather Pointy Boots ($39.94) | 2. Jeffrey Campbell Harvell Booties ($160) | 3. Marc Fisher Yamir Pointy Toe Booties ($179) | 4. Kendall & Kylie Finley Leather Booties ($190) | 5. Acne Studios Jensen Booties ($560)

The Stacked Heel Bootie

The comfort of stacked heel booties make them a great option for everyday wear, whether you are headed to the office, going out or just hanging around, these won't let you down!

1. Old Navy Sueded Ankle Boots ($42.94) | 2. Zara Leather Western Ankle Boots ($69.90) | 3. Kaanas Namib Booties ($139) | 4. Sam Edelman Petty Suede Booties ($140) | 5. Vince Easton Booties ($395)

The Over-the-Ankle Bootie

Reaching slightly above the ankle, this style is gaining popularity and looks particularly great when paired with cropped jeans or pants.

1. Zara Leather High Heel Ankle Boots ($89.90) | 2. Sam Edelman Blake Booties ($150) | 3. Free People Cecile Ankle Booties ($168) | 4. Marc Fisher Alisa Mid Shaft Booties ($210) | 5. Joie Chap Tassel Booties ($398)

The Chelsea Bootie

This clean and classic style not only goes great with just about anything, but thanks to its comfy heel and slip-on-and-go characteristic they also make for the perfect go-to booties. These will most likely become your favorite pair!

1. Topshop Kaiser Chelsea Booties ($70) | 2. Gap Chelsea Boots ($98) | 3. Madewell Chelsea Booties ($210) | 4. Diane von Furstenberg Jena Chelsea Booties ($348) | 5. Loeffler Randall Carmen Booties ($450)

The Python Bootie

If you're looking to amp up your look and spice things up a little bit, then I recommend a pair snakeskin booties. They are not just on-trend, but they also add a great visual element to any fall outfit.

1. Free People Cecile Ankle Booties ($168) | 2. Vagabond Kaley Leather Ankle Boots ($175) | 3. Marc Fisher Yamir Pointed Toe Booties ($179) | 4. Loeffler Randall Greer Python Booties ($475) | 5. Newbark Sabrina Booties ($785)

Cut-Out Booties

Cut-out booties not only edge up your look, but they are also a great way to transition your summer looks into fall. If you're still not ready to completely dive into fall footwear, a pair of cut-out booties is the perfect shoe style to make that transition.

1. Kaanas Thar Booties ($119) | 2. Steve Madden Austin-S Booties ($140) | 3. Jeffrey Campbell Cromwell Booties ($175) | 4. Jeffrey Campbell Taggart Cutout Bootie ($179.95) | 5. Matt Bernson Jagguar Booties ($299)