This post may contain affiliate links, which means we’ll receive a commission if you purchase through our link, at no extra cost to you. See our disclosure here.
Having a pair of comfortable and cute fall ankle boots are the best go to for their versatility and comfortability in the colder months. Not to mention, they can make a statement in your outfit. Today we are sharing 21 Insanely Comfortable and Cute Fall Ankle Boots. You won’t help to resist to put in your cart!
In the fall, you will probably only catch us in ankle boots. Investing in a good pair of boots is possibly the best fashion decision we have made thus far. One of our mottos, when we are shopping for new pieces is quality over quantity. If you invest in a couple of good pieces each season, the life of those pieces could last you years or a life time.
Five years ago, we invested in our first pair of Cole Haan Chelsea Boots and let us tell you, our life was changed. We took several trips to NYC and walked the city up and down in those shoes. No scuffs, no sore feet and they still look brand new to this date. The Cole Hahn Chelsea Boots had a little heel, but were the most comfortable shoes we have to date. Since that first investment, we have not wavered in our motto of investing in quality, especially when it comes to boots.
Investing in a good pair of boots is possibly the best decision you can make!
More Lifestyle Tips Here:
21 Things You Need For Your First Apartment in a Big City
15 Insanely Cool Electronic Gadgets You’ll Obsess Over
25 of the Best Cookbooks Online
How do I pick out the perfect fall ankle boot boot?
There are several things to consider when picking out a perfect fall ankle boot (or any type of boot!). These are tips that we swear by and consider when we are shopping for our latest fall ankle boots. You want to consider the conformability, style and versatility with outfit pairings.
1. Comfortability can come with a cost, but it is worth it!
As previously mentioned we have found that investing in a good pair of boots is the best decision you can make. We are not frivolous spenders and wouldn’t be saying this if we didn’t mean it. If you want enjoy your shoes for years, invest in a pair with good feet support. Chelsea boots seem to hit at the perfect mark on your leg, where they don’t seem to cut in or feel too tight, making them easier to walk in all day long.
2. Find Fun Styles!
No matter your personal style there are is a Chelsea ankle boot out there for you! We have 21 Insanely cute fall ankle boot styles your will love. This year, the top boot trends we have been seeing are combat, western, and English classic styles. The great things about boots is that they they can elevate an outfit and make a statement. So get fun with it!
3. Look for versatility!
When choosing Cute Fall ankle boots, look for versatility. The great thing about Chelsea boots are their ability to make a statement no matter the occasion. They can be dressed down, or dressed up with simple outfit tweaks. For example, chunky combat Chelsea boots can be dressed down with a pair of jean shorts and a sweatshirt and dressed up for a night out on the town with a cute mini dress.
21 Insanely Cute Fall Ankle Boots
1. Yale Chelsea Boot // Marc Fisher
These Marc Fisher Yale Chelsea Boots had to be top of the list! We have worn these for years and the quality and comfort are great. They come in several different colors and materials. We love the hardware detailing at the tip of the pointed toe. These shoes seem to have a slimming effect on your foot. A must-have classic and staple boot!!
2. Padmia Chelsea Boot // Marc Fisher
These Padmia Chelsea Boots provide a little hight from their platform soles. They are perfect for a casual weekend outing. Pair with cropped jeans and fun blouse!
3. Haidyn Bootie // Cole Haan
These Haidyn Cole Haan Booties are a great classic bootie and staple for any closet! Snatch a pair while they are on sale!!
4. Ridley Chelsea Boot // Micheal Kors
These modern, chunky sole Micheal Kors Ridley Chelsea boots are trendy yet, timeless. The elastic gore on the sides provide comfort for movement throughout the day. The Ridley Chelsea boots come in two colors – light cream and black.
5. Avery Waterproof Bootie // Naturalizer
Naturalizer exceeds in comfortable fashion!! We swear by their shoes!! The heels on these boots elevate the casual look and are a true staple for any closet.
6. Gallzy Boots // Vince Camuto
These boots are possibly one of our favorites in our list of fall ankle boots!! The higher heel and wrapped chain detail make these boots perfect for a night out on the town with your friends or for a date night.
7. Huey Studded Bootie // Dolce Vita
One word for these boots… FUN! They are classic, yet edgy. The heel, studs and contrast between the colors on these booties are a surprisingly fun statement piece to add to your wardrobe. They come in four colors – dark brown suede, dune suede, black suede and ivory leather.
8. Hilary Bootie // Sam Edelman
How stunning are these Sam Edelman Booties?! The rich tone of the leather and just scream fall fashion. The sleek classic style of these boots will last for years to come!
9. 2976 Faux Shearling Chelsea Boot // Dr. Martens
Keep your feet warm in the colder months with these Faux Shearling lined Chelsea Boots by Dr. Marten. They are perfect if you live in areas where you have colder fall and winter seasons and provide a good cushion and a bit of a platform.
10. Venetian Bootie // Soludos
The wrapped look on these suede Soludos booties add an extra dimension to a classic bootie style. The suede material is so comfortable and looks so effortless.
11. Duchess Boot // Thursday Boot Co.
We just discovered Thursday Boot Co. and loved their mission to provide comfortable and durable boots for activities. The rubber soles and elastic sides provide flexibility and comfort for movement. We love the worn-in look of these boots! They also come in a variety of colors and materials!
12. Kenia Fringe Bootie // Born
Western-style boots are all the rage this season! The Kenia Fringe Bootie from Born combines western boot trends and comfort in this Bootie. Pair these booties with a pair of cropped jeans and an oversized sweater this fall!
13. Raegin Platform Bootie // Treasure and Bond
These Platform Booties come in three colors – an olive, grey and ivory. Combat boots seem to never go out of style. These booties provide.a little extra height with a 1″ platform sole. For a casual look, pair with leggings and a sweatshirt. For a dressed up look, pair with a cute floral dress and leather jacket.
14. Courmayeur Valley Chelsea Boot // Timberland
These two toned Courmayeur Chelsea boots add a pop of color to an outfit and provide comfort and style for any casual outfit. The craftsmanship of TImberland is hard to beat! These are perfect for a casual look at the office or a Saturday coffee run!
15. Pola Studded Chelsea Bootie // Karl Lagerfeld Paris
We are OBSESSED with these Karl Lagerfeld Booties!! Adding these to our cart now!! LOL! The shine of the leather and wrapped studded band around the ankle gives this classic bootie style an elegant look.
16. Waxton Chelsea Boot // Franco Sarto
These sleek, slimming blocked heel boots come in 5 trendy colors. They hare made with a soft leather and have a cushioned sole, it may be hard not to get them in all colors for the fall!! We pay great attention to detail and fell in love with the stitching on the back of the boots and detail in the block heel.
17. Bealy Bootie // Franco Sarto
Franco Sarto Bealy Booties are so simple yet seem to still make a statement!! Once again, the attention to detail is noticed in the stitching and the hardware detailing at the back of the ankle. The beautiful, rich leather adds to the simple sophistication of the boot.
18. Rover Bootie // Rag and Bone
Rag and Bone’s Boots are made with excellent craftsmanship. These antique white booties are timeless and can be paired with absolutely anything! Snag them while they are on sale!
19. Cougar Firenze Glossy Chelsea Rain Boots // Cougar
Be prepared to take on any rainy day in these fashionable, modern Cougar rain boots. They come in 3 beautiful colors- black, ash blue and (our personal favorite) oyster!
20. Lennox Chelsea Stud Boot // Sorel
Sorel are masters of functional fashion! Take on anything the day brings with these fashionable, waterproof Lennox Chelsea Stud Boots.
21. Valorie Bootie // Cole Haan
We had to give you one more Cole Haan Boot! The Valorie Booties are made with a gorgeous mahogony leather and strips of elestic on the sides of the ankle for comfort. The GrandFøam cushioning technology provides for comfort when walking or standing. These shoes are great for the office or walking around town.
What boots are your favorite?!
We want to know! Keep in touch with us and follow Mozie Life on social media!
