If you’ve looked up the shoes every woman needs in her wardrobe, you’ve undoubtedly seen ankle boots mentioned multiple times.

It’s understandable. Ankle boots are a timeless wardrobe piece that most of us already own. I know I’m a fan: I pair mine with just about every outfit in the fall and winter.

In particular, I like to wear my ankle boots with jeans. From straight leg to wide leg to skinny, all denim cuts can work with ankle boots. But getting it right can sometimes be tricky.

There’s a lot to think about when wearing ankle boots with jeans. Some common questions include: What height should the boots be? Since you are also considering the outfit, the shoes must also fit it. Plus, which jeans are you wearing with your ankle boots? Straight, skinny, or wide leg? I wear different boots with different jeans and style the jeans differently depending on the boot. I can either tuck them in or wear them cuffed.

So, to help you style these classics, I’ll teach you everything you need to know about how to style ankle boots, plus some outfit ideas too!

Table of Contents

How to Wear Ankle Boots with Jeans: The Do’s & Don’ts

• Try cropped jeans. If you wear a cropped pair of jeans, they will hit right about where the ankle boots begin, so you do not need to worry about tucking in your jeans. So let the denim hit an inch or two above your boots. Note: Unless you’re going for a specific look, it’s best not to show a ton of calf between the bottom of the jeans and the boots’ top. For most occasions, your boots should hit above your ankle bone.
• Tuck your boots into your jeans only if they don’t bunch. I recommend tucking only with skinny jeans if your jeans are long enough to reach your ankle boots. Additionally, only do this if the opening of the boots is wide enough to fit the bottom of the jeans. Don’t try to tuck your jeans in if your boots are shorter or if your jeans don’t reach far enough down.
• Consider cuffing if your jeans are too long and not super skinny at the ankle. This is another option to keep your jeans from bunching up, so you don’t have to tuck them. The space between the boot and the cuff should show no more than a sliver of skin. Cuff them right above where the boot starts. Remember, cuffing is the best for short or medium-height ankle boots.
• Ideally, choose jeans to match your boots’ height. When your jeans are at a reasonable length and your boots are ankle height, you should be okay and have adequate space between them. So do nothing if your jeans hit above your ankle and your ankle boots hit at your ankle.
• Know the different styles. There are different shaft heights for ankle boots which can lead to confusion on how to dress ankle boots in jeans. As a rule of thumb, there are short ankle boots (hit right at or under the ankle bone), medium ankle boots (hit about an inch or so above the ankle bone), and tall ankle boots (hit a few inches above the ankle bone).

How to Wear Ankle Boots with Skinny Jeans

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