Ankle boots are hands down my most worn shoe come fall and winter. And honestly, also in the springtime. They go with jeans, dresses, skirts (both minis and maxis) and help to elevate any look where you may have just thrown a sneaker on.
The ankle boots are also super versatile in that you can wear booties with casual looks like jeans and tees, but can also be dressy enough to pair with a dress for the office or a date night. But I think one of my favorite things about an ankle bootie is that they help in transitioning pieces from summer to fall, or winter to spring.
So let’s dive into ways to wear ankle boots for fall so you can look and feel stylish this season.
How To Wear Ankle Boots
When thinking about how to wear ankle boots, there are a few things to keep in mind. There are so many different styles of booties and not every boot works with every outfit. Some ankle boots have a high ankle shaft or a low one. There are also ones that are tighter around the ankle and ones that are wider. Each of these goes with different items in your closet and may look better with certain pieces over others.
In my closet, I have a few different types of ankle boots that work with various items. I have this higher shaft boot and more tight ankle boots that are good for dresses and skirts. Or they’re good with leggings since they’re fitted and the boot lays nicely right over them.
Then there are these lower shaft Chelsea boots that go best with my jeans and allow a little ankle to show. They also work great with dresses and skirts too.
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Different Ankle Boot Styles
I’ve yet to truly find one ankle boot that goes with everything. With so many different styles and only some work with certain bottoms, you do kind of have to have a few styles in your wardrobe in my opinion. I don’t think you need a TON. But definitely enough to fit the types of outfits you own and wear the most.
Flat Ankle Boots
Flat ankle boots are great for everyday wear that are comfortable and stylish. These will go with most of your items from jeans, to dresses. But since they’re flat, you may not feel like they’re dressy enough for the office.
These can be a Chelsea boot or combat boot. Or a lug sole ankle boot. A flat ankle boot is definitely a more everyday casual option to choose from.
Low Cut Cutout Booties
There are also low-cut booties, ones with cutouts on the side like the ones featured above. There are tall shaft ankle boots that hit more mid-calf, versus ones that may hit right at the ankle.
We are seeing the lower cut, cut out style bootie to be trending down lately. This is due to the change in denim styles. These paired perfectly with skinny jeans back in the day. But now that we’re wearing more straight leg jeans, these are harder to style with that type of denim fit.
Warm Ankle Boots For Winter
For winter, there are winter ankle booties that are warm and toasty. These are usually waterproof and maybe are even lined with shearling to keep you warm. And then my personal favorite as of late thanks to ALL the rain are these waterpoof ankle booties.
Fashion Ankle Boots
There are also SO many different styles from western-inspired ones, to pointed-toe boots, to even white go-go-inspired booties. The options are truly endless and there are ankle booties for every outfit, every style and every price point.
Sock Booties
The sock bootie is one of the newer ankle boot trends. These are the perfect fit to pair with those straight leg jeans. They hug your ankle like a sock (there are varying levels of how snug) and go up a bit higher than our old school ankle booties from the 2010s.
These can be worn with straight leg jeans, cropped jeans, and your wider leg jeans too. Plus, depending on the style, you can wear these with dresses and skirts. I think they’re very cute with a patterned sock peeking out at the top too.
Ankle Boot Styling Tips
If You’re Petite
When you’re petite, or have short legs, it’s important to always keep in mind elongating the leg. That means usually adding a heeled bootie, a pointed toe, or at least rounded toe.
It likely also means you should avoid a mid-shaft ankle bootie. It can really cut you off if not done right. The only time a mid-shaft ankle bootie could potentially work is when you’re going monochromatic. So all black, or black with dark dark jeans, and so on. It’ll help to create a longer line for you and work to your advantage.
Choose The Right Jeans
For someone like me who lives in my jeans, I’ve come up with all sorts of ankle bootie and jean combinations in my closet. There are certain jeans that hit just right for certain boots in my closet.
Then there are some that require a really low ankle bootie to go with jeans that have a longer inseam. And then there are these Everlane jeans that I love, they’re basically a short inseam almost for a petite frame, that work with all of my higher shaft booties.
It seems silly that just a few centimeters of the boot or jeans will make a big difference, but it does. When your jeans start to puddle into your booties, it can look messy and undone. So keeping clean lines, good tailoring and the right boot will create an overall more flattering look.
When figuring out how to wear booties with your jeans, you just need some options! And that may mean a tailor, or quick hem with scissors, and you’re good to go. It makes all the difference.
Plus, with so many new jean styles right now from straight leg, to relaxed 90’s, flared and everything in-between, this will really dictate which boots you can wear with which jeans.
Best Ankle Boots For Winter
If you live in a super cold climate, you’ll probably want to reach for an ankle bootie that covers up your ankle with a taller boot shaft. This way you’ll stay nice and warm! You can also add some interest to your look by having a bit of your socks show too.
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9 Ankle Boot Outfit Ideas
Showing A Little Skin In Skinny Jeans
There are a few things you can do with skinny jeans and ankle boots. It’s all about your personal preference however, you want to keep ONE thing in mind. You do NOT want your jeans to bunch up around your booties. Period. And I would skip cuffing the jeans too. Either hem them, or don’t pair them with the boots.
My personal favorite way to wear my ankle booties with jeans is to show a little skin in between your jeans and your bootie (I love these Everlane crop skinnies, they go with ALL my booties with no bunching). This may mean only some of your jeans work with some of your booties though.
And while we are seeing a lot of shifting trends in the ankle boot world since the 2010s, I would stick to simple boots with modern and clean lines. Leave the funky laser cut booties, crazy details and so on to the donate pile. Basically, any style from this blog post is probably a no from now on.
Skinny Jeans Tucked Into Ankle Booties
The other option is to tuck your skinny jeans into your booties. This is more easily done with a taller shaft and one that’s a tad wider to allow a little room for your jeans. It is SO important to make sure you have the SKINNIEST of jeans on. You do not want bunching around the boot opening or you’ll look sloppy.
I love how Ashley of The Teacher Diva styled these block heel ankle booties with skinny jeans. It’s the perfect tuck, no bunching and the proportions are just right.
With Dresses & Skirts
The great thing about dresses and mini skirts is that really any bootie type can work. Whether it’s a tall shaft, wider, or narrow, doesn’t usually matter. When you’ve got a bare leg you can typically get away with any.
My only tip would be to try a few to see which makes your legs look the longest. Usually, a less chunky, more minimalist boot can flatter a shorter leg best.
White Ankle Booties
I’ll b honest, I’m not into this trend really. It’s so popular right now and I’m not sure how long it’ll stay. But if you’re into the white ankle bootie, they’re definitely a fun trend to take for a spin.
I think the only way I would personally wear this is how Amy of Fashion Jackson did here. A simple vintage light wash denim, neutral sweater and trench. It’s chic, stylish and feels super fresh but also classic at the same time. Not sure how she does it so effortlessly but it is GOALS.
With Maxi Skirts And Maxi Dresses
The ideal ankle boot to style with a maxi dress or skirt, in my opinion, is a tall block heel bootie. You can play around with the shaft height and may want to keep the shaft width in mind to make sure it’s not too loose. Loose boot, long skirt, may feel a little messy!
However, I definitely prefer a tall heel with a maxi to elongate you. I love this plaid wrap dress that Laura of Louella Reese styled with these stunning brown leather ankle boots.
With Cropped Straight Leg Jeans
This is a great example as to why it’s important to keep in mind the height and width of the boot shaft. A cropped jean requires a more fitted boot that lays close to your body. This way it’s sleek and not messy. And there are many different options to choose from here from high heeled, to flat, and so on. The main thing to look for is the higher shaft and snug fit and you should be good to go!
When thinking about how to wear boots with straight leg jeans, you want the jeans to fall nicely over them and not look bulky or that the jeans are bunching. This also works for boyfriend jeans or 90’s relaxed jeans. The closer to the body the boot is, the better.
I just LOVE this outfit from Kim of Love Cloth, the blazer and hoodie are perfection for fall layering.
Combat Boots With Leggings
My favorite way to make my lululemon align pants work for every day (yes I do that) is to add a bootie with a tall shaft to cover my ankle. Think combat boot or Dr Martens to accomplish this. It makes them look sleek and like they’re real pants! Winning! I think it’s key to cover your ankle and any skin between the leg and pant when rocking leggings with boots.
Boots For The Winter
When picking out ankle boots for the winter, always get cozy booties that cover those ankles. I love these fuzzy winter boots that Jess Ann Kirby styles with faux leather leggings and a cozy sweater. You can always add a fun sock to peep through too for a little more texture!
How To Style Boots If You’re Petite
My friend Cathy has a petite frame at just 4’11 so she’s mastered the art of making her legs look longer than they are. A few things to consider are a rounded toe or pointed toe bootie to elongate the leg, a heel is your best friend and always choose an ankle bootie that has a lower shaft height. This will help elongate the leg.
Another trick is to go all one color like black jeans with black booties. It will elongate your legs BIG time. This way you can also wear all different ankle boot shaft heights without cutting off your legs making them look shorter than they are.
