How To Wear Ankle Boots 9 Ways

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. They’re super versatile in that you can wear them 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.

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 that allow a little ankle to show. They also work great with dresses and skirts too.

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How To Wear Ankle Boots 9 Ways

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 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.

For that in-between weather, a peep toe or open toe ankle bootie is a fun trend to wear. These laser cut peep toe booties are super fun for spring and fall.

There’s also low cut booties, ones with cut outs in the side like the ones featured above. There’s tall shaft ankle boots that hit more mid calf, versus ones that may hit right at the ankle. For winter, there’s winter ankle booties that are warm and toasty. And then my personal favorite as of late thanks to ALL the rain are these waterpoof ankle booties.

And 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.

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 combination 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.

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


Jessica Wearing Everlane Denim

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.

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.

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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.

Photo Credit → The Teacher Diva



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, 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 longest. Usually, a less chunky, more minimalist boot can flatter a shorter leg best.

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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.

Photo Credit → Fashion Jackson



With Maxis

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.

Photo Credit → Louella Reese



With Cropped 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. You want the jeans to fall nicely over them and not look bulky. This also works for boyfriend jeans or straight leg jeans too.

I just LOVE this outfit from Kim of Love Cloth, the blazer and hoodie are perfection.

Photo Credit → Love Cloth



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. 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.

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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!

Photo Credit → Jess Ann Kirby



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 is 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.

Photo Credit Poor Little It Girl →

Photos by Hannah Lozano

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4 Comments

  1. 2.19.20
    Rachel said:

    I am loving your snakeskin booties and trench coat combo for spring! So fun. Love all of these outfits and tips too, especially for my short sausage legs 😉

    Rachel
    http://www.hello-her.com

  2. 2.19.20
    Laura Leigh said:

    UMMMM you just completely made my day!! Thank you so much for including me in this round up! I really appreciate it Jess! Love seeing a variety of styles and stylings. Of course crushing on your snakeskin ankle boots.

    xo Laura Leigh
    http://louellareese.com

    • 2.19.20
      Jessica said:

      You’ve inspired me to style more dresses this winter. I am guilty of only wearing jeans! Need to branch out and loved your outfit so much.

  3. 9.24.20

    I am so eager to break in a new pair of ankle boots! This is a great round up of styling options.

    Amanda || Affordable by Amanda