
Wondering how to style ankle boots? Here are 12 ankle boots outfit ideas for you to try year-round.
My friends have told me they’ve struggled with ankle boots outfit ideas when it comes to getting dressed. Well, I’m here to help you find the right ankle boots and offer 12 ways to style them so you’re never in a style funk!
I consider ankle boots like the supporting actress in an outfit. It helps complete the look, but it doesn’t have to be the main attraction. Do you know what I mean? What I love about them is that they’re easy, versatile, and accessible. They come in multiple heel heights, styles, and colors.
So enough rambling, let’s get into ankle boots outfit ideas!
1. Skinny Jeans
@brooklynblonde1, @sincerelyjules, @laurennicolef
How to wear ankle boots with skinny jeans is number one. This is because it’s the number one highly asked ankle boots question in Google SEO. Skinny jeans are accessible and we all own a pair, so it’s understandable that we all want to know how to style them with ankle boots.
Note: You don’t want to wear skinny jeans that are too long, because they’ll bunch up at the ankle and it’s not a cute look. I suggest wearing ankle-length jeans. This not only elongates your legs but is also a more flattering look and silhouette.
Shop ankle Boots with skinny jeans:
2. Leggings
So, how to wear ankle boots with leggings was the second most asked ankle boots question in Google. There are a few ways to style ankle boots with leggings, but suggest low cut booties with leggings that are not too long to avoid bunching at the ankle. With low-cut booties, you also show some ankle between the shoe and legging which elongates your legs.
Also try detailed ankle boots with simple leggings, and the shorter the heel of the bootie, the shorter your top!
Shop ankle boots with leggings:
3. Long Dresses
Whether for Spring or Fall, you can wear ankle boots with long dresses. I love to wear them with a warm turtleneck, knit dress during the winter, but they also look cute with a long maxi dress for Spring.
4. Mini Skirts
@ivanka.dekoning, @flauntandcenter
Can’t talk about dresses without skirts. Either short or long, ankle boots can elongate your legs with skirts. During Fall and Winter seasons, try them out with tights.
Shop ankle boots with skirts:
4. Straight-Leg Jeans
@lucywilliams02, @ivanka.dekoning
Straight-leg jeans are my absolute favorite style of jeans and love to wear them with ankle boots. You can roll up the hem to show some ankle with low cut boots or a second skin boot.
Also, you can get ankle length, straight-leg jeans to expose more leg with your ankle boots.
5. Voluminous Dress Silhouettes
Voluminous dress silhouettes are so cute styled with a feminine ankle bootie or even with a chunky ankle boot, like a combat boot. It’s fun to play with the juxtapositions of feminine and edgy.
Shop chunky ankle boots:
6. Cowboy Ankle Boots
@lainyhedaya, @thefashionguitar
The Western trend is here for the next couple of seasons. So try this bootie with a short dress and long sleeves
Shop cowboy ankle boots:
7. Relaxed Fit Trouser
Relaxed fit trousers can pair nicely with sleek ankle boots or tuck into a chunky lug boot.
8. Midi Skirt
So midi skirts are tricky. You have to be careful on the ankle book, as you do not want to show too much ankle. Then the proportions of the skirt and boot will look off. The right ankle boots are the ones that are slightly higher, so it leaves very little leg showing for a nice silhouette.
Shop ankle boots to wear with midi-skirts:
9. Boyfriend Jeans or Dad Jeans
To make this look work, make sure your ankle boots have a heel. With baggy pants, you want to elongate the body for a more flattering silhouette.
10. Wide-Leg Jeans
Whether cropped or floor-length, wide-leg jeans work so well with ankle boots.
11. Monochrome

Love a chic monochrome moment, and it works so well with ankle boots for the perfect head-to-toe look!
12. Wear To Work
@lisahahnbueck, @natalieoffduty
Interested in how to wear ankle boots to work? There are so many options, but what’s most important is getting proportions right. Here are some examples of how to wear ankle boots to work.
Shop ankle boots for work:

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