Last Updated on January 23, 2026 by Martina McKeough
As the weather starts to get chillier and wetter I start to put away my sandals and slides and start thinking about the next seasons footwear. I have a whole range of shoes and boots that I use in autumn but one of my year on year favorites are ankle boots. Wearing ankle boots for fall makes sense. They protect my feet from the wet and cold, they go brilliantly with my jeans and dresses and they look stylish as well.
Ankle boots also come in a huge range of different styles which means that you can switch up your look depending on your outfit or occasion. I tend to choose practicality and comfort because who wants foot pain.
Here are some of my favorite styles and designs and how you can wear them.
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Chelsea Boots
Chelsea boots are a classic for a reason, they are easy to take on and off! These boots go with everything are simple to slip on when I need to pick footwear in a rush.
I tend to opt for Chelsea boots in leather because they last longer, are breathable and work well in colder weather. I also like to choose designs with a really simple shape so they go with more of my outfits. I think I am a bit of a minimalist rather than a maximalist so plain chelsea boots suit my aesthetic.
My top top apart when choosing them for autumn is to be smart and pick ones with lug soles so that you are not slipping on wet sidewalks when you are out and about.
Sam Edelman Women’s Jazmine Chelsea Boot
Lace Up Boots
Lace up boots are also great but obviously take a little more time to do up.
They do however have an advantage over Chelsea boots in that they are more secure on your feet. I can do up the laces so they fit better and they are less likely to move around on my feet.
There are thousands of lace up styles available from the classic leather look with flat heels to the more sporty offerings that I kinda love from Sorel. Think about where you are going to be wearing them and whether you are looking for a more formal or informal design when out shopping.
Sorel Women’s Kinetic Impact Conquest Waterproof Shoes
Combat Boots
Back in the day I used to be a goth (don’t judge me) and Doctor Marten boots were always on my feet.
I’m still a bit of a sucker for that edgier look but my feet are not always so happy with the breaking in period now that I am older.
So I found a happy medium with these Vionic boots that give you the look but aren’t quite so difficult to mold to your feet. You can thank me later for introducing you to a footwear brand that is kinder to your feet.
Vionic Lani Boots
Pointed Toe Boots
I reach for these when I want to feel a bit more put-together without sacrificing comfort.
They instantly dress up jeans or trousers, and elongate your legs (bonus!). These are great for going out in the evenings and you want to ditch the really casual look.
Just make sure to get the right size as the last thing you want is pinched sore toes.
Franco Sarto Women’s Anna Ankle Boot
Heeled Ankle Boots
Heeled ankle boots always look good and are great for work or for a night out.
These can look sophisticated or edgy depending on how you style them plus they go really well with skirts and dresses.
Try and keep your look classy by buying a medium height pair rather than opting for something sky high. They will look better plus you’ll still be able to walk in them at the end of the night.
ALDO Women’s Noemieflex Block Heel Ankle Boot
Waterproof Ankle Boots
Whilst I have a closet full of smarter ankle boots I always have a pair of more casual practical ankle boots as well.
These are the kind of boots that are great to use if you are walking the dog, wandering round soggy fields at an event or for short hikes.
There is nothing worse than getting wet feet from rain sodden ground so I keep these for when I need something robust and practical to keep my feet dry.
Hunter Waterproof Miana Chelsea Boot
Cut Out Ankle Boots
I wear these in the earlier part of autumn when it’s not too cold yet.
This style of boots is great for transitional weather and look perfect with cropped trousers or bare ankles and midi skirts.
They let your feet breathe while still feeling autumn-appropriate plus they are good for spring weather as well.
TOMS Everly Boot
Textured or Statement Ankle Boots
Finally it’s always nice to have something a little bolder in your closet to add a little bit of personality to your outfits. Whilst I tend to stick to plain styles that doesn’t mean you have to.
Think boots in animal prints, metallics or with embellishments.
Don’t go too wacky so that you get laughed at in them, instead pick designs that work well with your current wardrobe but which add interest to what you already have.
Steve Madden Alston Ankle Boot
What Autumn Ankle Boots Would You Choose?
So which ankle boots for fall would you choose to add to your footwear collection?
Remember you don’t need them all just one or two styles to build your shoe wardrobe so don’t panic about blowing your budget buying every design.
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