Stylish women’s booties are a must for fall, winter…and spring, come to think of it. That’s ¾ of the seasons y’all, so we gotta stay on top of our ankle boots. With today’s massively delicious selection that’s not a problem, but oof, women’s booties of the past were often disconnected from what actually looked good with clothes. There is a specific style of ankle boots from the past 20+ years that I am still purging from my clients’ closets that make me shake my head. They are wide at the ankle and hit right at the ankle bone so it makes your legs look terrible in dresses, and only long boot cut or cropped, cuffed straight-leg jeans technically make sense, but they don’t look particularly good.
Best Stylish Women’s Booties
The most versatile and flattering women’s booties have an almond toe, are fitted to the ankle, and stop about an inch and a half above the ankle bone. Other stylish women’s booties I am loving are lace-up booties or slim combat boots. Below I have the most scrumptious shopping list of my favorite booties in all the core colors as well as some fun ones. What are the core colors? I am so glad you asked. The core bootie colors for a flexible wardrobe are:
- Off White Booties
- Black Booties
- Tan Booties
- Blush Booties
- Navy Blue Booties
How To Wear Stylish Ankle Boots
Ankle booties are all about cropped or cuffed straight-leg jeans, leather or tweed skirts, and dresses, with an emphasis on sweater dresses. They also pair with leggings and a single-cuff skinny jean. Stylish women’s booties are very versatile though. If you have a slim leather bootie, you can pair it with something as light as a thicker silk dress. And if you are pairing booties with cuffed straight-leg jeans, feel free to sport a sock in a complementary color peeking out.
How To Protect Your Stylish Ankle Boots
Due to the delicacies of suede and lighter color ankle boots, it is vital to spray your brand new boots with a suede or leather protectant before you wear them outside. This spray makes a world of difference. I actually spray all my new shoes. It keeps them clean dramatically longer. Make sure you clean and respray them at least once a year. When you take care of your shoes, they take care of you.
Marc Fisher Jina Pointed Toe Bootie
These white booties are such a staple in my wardrobe. You can see how I styled them with a dress, here, and with wide leg cropped pants, here. They’re available at Nordstrom and Bloomingdale’s.
Free People Sienna Ankle Boot
These booties are available at Nordstrom and Free People.
Sam Edelman Codie
These boots are available at Zappos and Macy’s.
Naturalizer Dario Wedge Booties
These booties are available at Macy’s, Zappos and Nordstrom.
Alohas Watercolor Ankle Boot
I have these booties in a fabulous hunter green color, which is sadly sold out. But I’m loving this versatile beige color too. These ankle boots are available at Madewell and Alohas.
L’Agence Jeanne II Pointed Toe Bootie
These booties are available at Nordstrom and L’Agence.
Vince Camuto Women’s Donenta Lace Up Booties
These booties are available at Bloomingdale’s, Vince Camuto, Zappos and Nordstrom.
Franco Sarto Waxton
These ankle boots are available at Zappos and Macy’s.
Marc Fisher Women’s Lucien Lace Up Booties
Matisse Caroline Ankle Boot
These boots are available at Matisse and DSW.
Intentionally Blank Rachel Heeled Boot
Free People Lawless Fringe Western Boots
As you may remember, Free People is one of my go-to brands, especially for cowboy boots, fringed garments, and suede — and these booties embody all three of those elements.
Sam Edelman Women’s Garret Lace-Up Lug-Sole Combat Boots
This is the slim combat bootie style I mentioned that I’m loving right now. You can see how I paired these with a sweater dress, here. These boots are available at Macy’s, Zappos, and Nordstrom.
Daniella Shevel Milani
Sarah Flint Perfect Zip Bootie 70
Tory Burch Miller Mixed-Materials Lug Sole Boot
These boots are available at Tory Burch, Nordstrom, Bloomingdale’s, Zappos, and Neiman Marcus.
Marc Fisher Jarli Pointy Ankle Boot
These stylish women’s booties are available at Marc Fisher, Amazon, and Nordstrom.
M. Gemi The Cristina
Zadig & Voltaire Tyler Vintage Stars Ankle Boots
Momo Asteria Sequin Ankle Boots
Stylish Ankle Boots From Years Past
I originally wrote this post on stylish women’s booties years ago and update it regularly due to its popularity. I’ve left these photos below for nostalgic purposes. Whenever I update older posts, I love to hold on to a collection of images as a bit of a time capsule so we can watch how our style evolves.
Banana Republic Round Block Heel Ankle Boots
I am so impressed with these Banana Republic Round Block Heel Booties. They are affordable, comfortable and versatile. They can be dressed up or down with cuffed jeans or nicer sweater dresses.
Tip: Due to its light color, it is even more vital to spray these ankle boots with Suede Protectant before you wear them out.
Vince ‘Dryden’ High Block Heel Ankle Boots
These Vince ‘Dryden’ High Block Heel Booties are fabulously comfortable, flattering, and versatile. They can pair with leggings, skirts, and dresses for a chic look. You can even tuck in standard skinny jeans if they are really snug at the ankle.
Tip: Due to the delicacies of suede, it is vital to spray these ankle boots with Suede Protectant before you wear them out.
Stuart Weitzman ‘Notazzie’ Ankle Boots
I am insane for these Stuart Weitzman ‘Notazzie’ Booties. They are wonderfully comfortable and the epitome of chic ankle boots. Wear them with dresses and skirts for the most gorgeous looks.
Tip: Due to its rich color, it is even more vital to spray these ankle boots with Suede Protectant before you wear them out.
Salvatore Ferragamo Metallic Leather Ankle Boots
Fancy price for fancy shoes. These Salvatore Ferragamo Metallic Leather Booties are amazingly more comfortable than the usual Salvatore Ferragamos shoes and truly gorgeous. The copper gold and almond toe make these a must-have for the truly fashion forward gals on V-Style’s subscriber list.
Tip: Due to its rich and rare color, it is even more vital to spray these ankle boots with Leather Protectant before you wear them out.
Kenneth Cole New York ‘Estella’ Tassel Tie Ankle Boots
These Kenneth Cole New York ‘Estella’ Tassel Tie Bootie in burgundy are so cheeky and fresh for fall. These will be gorgeous with dresses and skirts, but you can also tuck in standard skinny jeans if they are really snug at the ankle. One note, this is a pull-on bootie with no zipper. To achieve that lean look on your ankle, you need to tie the bow the on the side of the bootie each time you wear it. I personally find it easy, but some of my clients may not like that.
Tip: Due to its rich and rare color, it is even more vital to spray these ankle boots with Suede Protectant before you wear them out.
Kenneth Cole ‘Reeve 2’ Metallic Block Heel Ankle Boots
Kennth Cole is killing it this boot season. The Kenneth Cole ‘Reeve 2’ Metallic Block Heel Bootie is just another metallic bootie option for those wanting an edgier look. Besides the darker gold shade and chunkier heel, that are quite similar to the ‘Caylee’ ankle boot mentioned earlier.
Tip: Due to its delicate and rare color, it is even more vital to spray these ankle boots with Leather Protectant before you wear them out.
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