When ankle boots first gained popularity, I wasn’t too sure about the trend. I didn’t know if I could pull them off, and I wasn’t sure if they were worth the price, especially if they were a fad. In 2016, I finally decided to buy my first pair and have never looked back. I wear them constantly.
I loved them so much that I bought them in camel suede just a few weeks later. Needless to say my love for Rag & Bone ankle boots grew even stronger! The thing about these ankle boots is they’re not only on trend, they were built to last! I can honestly say I don’t think the ankle boot trend is going anywhere. They look amazing with skinny jeans, high waisted denim, dresses, skirts, and shorts too. Over the last few months, I’ve featured a few fabulous suede boots and Western-inspired boots (which are a MUST this season) on the blog because they are just so popular.
Today, I wanted to share a few gorgeous leather ankle boots that are classy, chic, and very trendy! They will be a staple in your wardrobe, I promise. I love wearing mine in the fall with my favorite basic tops, suede moto jacket, and jeans; they’re also great with leggings and an oversized sweater. When I feel like dressing up I’ll pair them with a cute boho chic dress and my favorite distressed denim jacket. Honestly, the options are endless!
If you’re searching for a new pair of leather ankle boots for fall and winter 2020, you’re in luck. Today, I’m excited to feature 20 fabulous leather ankle boots that you are sure to love.
This post was updated on March 27, 2020.
The best leather ankle boots under $100
It’s no secret snake print is everything in the world of fashion for 2020! These fabulous Blondo Need Waterproof Booties are not only perfect for fall and winter rain storms, but they’re deeply discounted. They’re on sale for less than $85!
It’s hard to find a great pair of shoes under $100 these days. These cute Western inspired pointy toe Splendid Paige Booties are not just under $100, they’re on sale and under $60. They’ll look great over your favorite skinny jeans or with a distressed denim skirt on a warm fall day.
This pair of Vince Camuto Gigietta Booties is an absolute must for women of all ages. They come in 11 different colors, prints and styles. I love everything about them, especially the wood block heel. They’re currently on sale and perfect for fall and winter! They’ll look great with your favorite leather jacket, suede moto, a cute cardigan and so much more! Which color is your favorite?
Fun athleisure inspired ankle boots
It’s no secret, the athleisure trend is hotter than ever! I couldn’t be happier, I love my white sneakers, pink tennis shoes and I’m currently coveting these fun athleisure inspired leather ankle boots. These Linea Paolo wedge booties will look great with your favorite leggings or skinny jeans! Word on the street is they are super comfortable too. They’re great for travelers or students. When I was in college I loved dressing up, but the campus was so large there was a lot of walking. I would have given anything to have comfy shoes that I could have paired with my outfits! These would have been a must! PS: They come in so many different prints, colors, fabrics, in suede, or leather. PS: They’re currently on sale (40% off). Some colors are as low as $40!
Obsessed With Embellished Leather Ankle Boots
I’ve been obsessed with everything embellished for as long as I can remember. The first designer handbag I ever purchased was my Alexander Wang Rocco bag mainly because I couldn’t get enough of the rose gold studs! These days my heart goes pitter patter for everything Valentino Rockstud and nearly everything with an embellishment or a rocker chic stud. If you love this trend as much as I do, you’re in luck. Today, I’m excited to share a few pairs that are not only perfect for fall but will be a staple in your wardrobe.
I have been coveting a gorgeous pair of Chloe stud ankle booties for years now. Now that the Western trend is hotter than ever, I’m fairly certain I need them. I love everything about these beautiful shoes – from the style to the gold buckles and the gold studs. They are perfection. These stunning leather ankle boots come in black or in white, which just happens to be super popular for 2020!
These exquisite Rockstud block heel booties are an absolute dream! They are beyond stunning and will always be on trend. They’ll look great with your favorite pair of skinny jeans, leather pants, leggings, dresses and more. These gorgeous ankle boots are available in the color black with gold studs or light cuir with gold studs!
Classic Black Leather Ankle Boots
Are you searching for a gorgeous pair of leather ankle boots that you can wear anywhere and everywhere? This season I went on the hunt for a few fabulous pairs of ankle boots that are not only perfect for the office but for church, date night, holiday parties and more! Without further ado, here are a few classic leather ankle boots you’ll love.
This black leather embossed pair of Alva ankle booties is a favorite! They’re chic, sophisticated and will look amazing on! These boots come in a variety of colors and materials – from suede to leather! They truly have something for everyone. PS: They’re currently on sale and 25% off!
Must have block heel leather ankle boots
The block heel shoe trend has been going strong for at least the last few years. This is one of my favorite styles because they are so comfortable and wearable. They’ll pair well with a variety of outfits – from classic to boho.
This trendy pair of Steve Madden Natalie Pointed Toe booties is under $110 and comes in four different colors including classic black, which will pair well with everything in your closet. You can wear them to the office, church, date night, brunch and more. I can’t wait to pair them with my favorite plaid tops, chunky sweaters and cardigans this season.
I simply adore these chunky heel Villa Rouge Loden Boots in the color bourbon!
Leather ankle boots that will dress up any outfit
One thing is for sure, we all need a great pair of dressy boots that we can wear to a variety of winter events, whether it’s a family gettogether, a holiday party, or any type of celebration with friends. Here are a few gorgeous dressy leather ankle boots that will look amazing under your favorite trousers, over your skinny jeans, with dresses and more.
How fabulous are these stiletto heel Freddie booties? I adore everything about them, especially the price point! Can you believe they’re less than $140? I can’t either. These fabulous boots are available in black and in white.
These beautiful GUCCI Indya Pleated Bow Tie Booties are an absolute favorite! They’re available in two colors and will dress up any outfit.
The Trendiest Leather Ankle Boots For Women For 2020
Croc Embossed and Snake Print Leather Boots
White Boots Are A Must
If you’re shopping for a new pair of white ankle boots, you can’t go wrong with these fabulous square toe Miista Marcella booties! They’re absolutely stunning and as popular as ever.
Must Have Dr. Marten Leather Boots
If you grew up in the 90s, I can almost guarantee you had a pair of Dr. Marten boots (aka Docs, Doc Martens). They gained popularity during the grunge movement, but I can still remember wearing them well into 1999!
I was surprised to see them at my favorite retailers earlier this year, and according to In Style, Doc Martens were spotted during many shows at the 2020 NYFW. They are destined to be huge for spring and summer 2020! If you’re eager to get a start on your spring and summer wardrobe, your best bet is to grab a pair of Docs. PS: They’re currently on sale and 25% off for a limited time.
A few weeks ago I featured a few must-have Western ankle boots on the blog, and it’s quickly become one of my most popular posts! Every day I’m stumbling on new boots that I wish I could add to it. There are so many great boots this season, it’s unbelievable. This morning I was doing a little online shopping and fell in love with this pair of Frye Billy Stud Short Boots. I’ve long been a fan of Frye boots, and have a feeling I will soon be adding them to my collection. They’re currently on sale and over $110 off.
Discover more fall and winter fashion finds in the Candie Anderson fall and winter fashion section: https://candieanderson.com/fall-winter-fashion