How To Wear Ankle Boots With Skirts – Style Guide

If there’s one item of clothing most of us have but always seem to keep hidden away in the closet; is a smart pair of ankle boots.

And we get: sometimes finding the right time and place for them can be a challenge.

How To Wear Ankle Boots With Skirts – Style Guide

But never fear as today we’ll explore some of the best outfits for ankle boots and pair them with a selection of skirts that come in an assortment of colors and styles that can be worn either in the summer months or during the winter.

Because there are many to choose from, we’ve selected our favorite picks that should be the easiest to choose from, and many of the skirts we’ve featured are going to be found in a typical closet.

How To Wear Ankle Boots With Skirts

Before we get into our favorite ankle boot-skirt combinations, let’s go through the basic guidelines you should keep in the back of your mind.

These simple guidelines are not hard-and-fast rules but will likely help you with the basics, in case you’re worried about pulling off a fashion faux-pas.

If you’re looking for a casual look for the daytime, then we recommend you go with a chunky ankle boot either in black or brown. Combine these with a denim skirt, skater skirt, or something above the knee that will work well.

If you’re looking for a more sophisticated look, then go with a heeled ankle boot that has a shaft that fits with your calf. This creates a more formal attire and would pair well with a pencil skirt that could be used as an office look.

What Types Of Ankle Boots Are There?

This would be an easy task if there was only one type of ankle boot, but there are many different variations out there.

Before we get started, have these different styles of ankle boots in mind, as this will help you style a skirt much more easily.

No Or Flat Heel

These ankle boots by definition are going to have a more relaxed feel to them, And are perfect for casual occasions.

This type of boot will have a low or no heel and will look great with flowy dresses and shorter skirts.

Low Block Heel

We would classify a low block heel as the middle-of-the-road option, meaning that it’s one of the more accessible choices of ankle boots.

This heel is large enough to elongate your legs and tighten up a skirt, but it’s also low enough to be a comfortable choice for all-day wear.

They are versatile because they go with most skirt lengths, but they also work well with jeans and pants making them a popular choice for a wide array of outfits.

High Block Heel

The higher the heel, the more dressy it’s going to be, and many women choose this type of heel when they are trying to maximize their figure, i.e. a night out or for dinner and drinks with friends.

If you want the heel with the most femininity and don’t mind sacrificing comfort for fashion, then opting for a high block heel is your go-to choice.

Stiletto Heel Vs. Wedge Heel

Stiletto Heel Vs. Wedge Heel

A stiletto heel gives off a more glamorous feel and should be reserved for evening wear, whilst a wedge heel offers more comfort.

Keep in mind the activity or event you are dressing for and the type of skirt as these will play a role in the type of ankle boot you choose.

1. Corduroy Mini Skirt

We start off our list with an elegant number that can be found somewhere between casual weekend wear and going out for cocktails with the girl’s vibe.

Owing to the fact that most skirts come in brown color, this corduroy option can be paired with a number of different tops, but we like a plain white shirt or blouse, along with black ankle boots.

To make this outfit stand out, add a black leather belt with a small brass buckle, either in silver or gold depending on your preference. This helps create separation between the top and skirt.

If your goal is to wear this in the winter, you can also add a gray cardigan for an added layer to help keep you warm.

2. Denim Skirt

As a casual daytime outfit, nothing stands out better than a denim skirt and ankle boot combination. It’s smart, fashionable, and flattering.

We would go with a light wash or indigo denim paired with a crop top. Choose something more colorful like mustard, or something simple like black, as well as black tights.

In terms of what color heels to wear, either a black or brown ankle boot works here.

If you want to add some extra color, go with an ankle boot that has either a metallic or golden heel to help break up the outfit ever-so-slightly; especially if you are planning to wear black tights.

3. Leopard Print Skirt

If you’re looking for an outfit with a more conservative skirt length, but still has the elegance and dazzle of a skirt that screams style, something like a lightweight printed skirt can work well for the warmer seasons.

Again we would keep it simple on the footwear, and go with an all-black pair of ankle boots. A white top works well here, or even a black top if you want to match your body and feet.

But we’ve also seen a cream or more neutral color being pulled off with a black top and black leather jacket.

4. Midi Skirts

Midi skirts are another safe option, as they allow for a skirt that rides below the knee, or just above it.

When trying to pair ankle boots with a midi, you should opt for a sleek pair that ideally has a tall shaft that will fit the calf in a seamless line.

And efficiently avoid flat ankle boots and go with a nice heel, to effectively elongate the legs which allow for the skirt to become accentuated. We want to show off that skirt in all its glory!

Again, black ankle boots with a colored heel will work with a wide array of midi skirt styles, so play around and see what works for you and your skin tone.

5. Long Skirts

Similar to the midi skirt, a long skirt will typically be worn well past the knee and towards the ankles, although there will still be some skin in between your ankle boots and skirt.

Showing off ankle boots is a more stylish approach to the long skirt and ankle boot combination, and we certainly don’t want to be drawing the boots in the material so make sure your skirt fits well before going with this option.

You want to go with a tall shaft again. In terms of color, you can choose brown heeled ankle boots as these will work well depending on the weather. We find this color works well in the warmer months with white and more neutral-toned shirts.

6. Leather Skirt

This is a great option for those that love to wear leather or faux leather around the waist. Mini skirts are hot, period; and picking a well-fitted leather skirt will go with a wide range of colors and options of tops and ankle boots.

One great option is a black leather skirt, red jumper or red sweater, with red ankle boots.

Not only is black and red together a fierce combination, but it’s also a color scheme that can fit many occasions, and wouldn’t be out of place at the mall or the cocktail bar.

7. Short Skirts

Short skirts are great because you wear a wide range of ankle boots, but we particularly like a lower-heeled boot which gives a more casual vibe. However, feel free to try a heeled ankle boot for the evening.

Make sure to match your tights with your boots, if you are wearing tights, or at least match them to the color palette of your skirt instead.

A good rule of thumb for matching colors is to choose lighter-colored ankle boots with lighter-colored skirts, i.e. white boots with a white skirt or brown boots with a brown patterned dress.

Otherwise, go with a black pair to match a black skirt and a white or red top.

8. Pencil Skirt

Pencil skirts are great for the office, and if your employer allows for them to be worn with boots, you should give them a try.

When you are pairing a pencil skirt with ankle boots, you want to avoid chunky style options as this fails to accentuate the pencil skirt.

Instead, you should opt for a sleek heeled boot that will not only elongate your legs but will also match the silhouette of the skirt. 

If you want to take this to the next level, match the boots with the color of the skirt. This will create a cohesive color scheme. It’s professional, but also very sexy.

Final Thoughts

Choosing the right skirt and ankle boot takes some practice. But following our tips will ensure you nail the look every time.

Jenna Reign