Can You Wear Ankle Boots With A Midi Skirt Or Dress?

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Figuring out what shoes to wear with your midi skirt can be tricky at times. Are you going for a high fashion look or just a casual outfit to hang out with some friends? For your convenience, we pulled together a guide on wearing ankle boots with a midi skirt or dress.

You can certainly wear ankle boots with a midi skirt or dress. Whether you decide on a bright pair of boots or something more neutral, they will go well with a midi-style outfit. We recommend a heeled ankle boot or even a combat style with a midi skirt or dress to give you some height. Regardless, make sure to stick with similar colors and patterns to keep your outfit cohesive.

As we begin, we will show you some midi skirt and dress ideas with ankle boots. Although this style can be challenging to work with, there are plenty of good options out there. With that said, let’s get right into this topic!

A woman sitting on chair wearing skirt and ankle boots, Can You Wear Ankle Boots With A Midi Skirt Or Dress?

What Shoes Or Boots Go With Midi Dresses?

Depending on your style, there are a few good footwear options to try with a midi dress. Some of our recommendations include heels, sneakers, boots, and sandals. If you are dressing for the summer, we suggest sticking with open-toed heels or a pair of sandals. For winter, try boots or comfortable, warm sneakers. Midi-style dresses cut off around your shin, so whatever you wear needs to pair well with that type of look.

How Do You Wear Ankle Boots With A Midi Dress?

When it comes to styling a midi dress with ankle boots, keep your outfit simple. Considering your dress is on the mid-length side, make sure to choose a heeled ankle boot to finish off your look. This will not only add height to your outfit but also give it a more high fashion feel. If you aren’t into heeled boots, a platform or combat style is also a good option to try out.

ADRIENNE VITTADINI Women’s Tammy Ankle Boot

Here is a heeled ankle boot from Adrienne Vittadini to pair with a midi skirt. These boots are 100% leather, have a synthetic sole, and are 3.5 inches tall.

Check these boots out on Amazon here.

Can You Wear Boots With A Midi Skirt?

A fashionable woman wearing a long winter coat and thick funky boots walking by on the city streets

If you want to try a pair of boots with your midi skirt, we say go for it! Like the midi dress, boots look great with this style and add some fashion to your outfit. Generally, try to keep your boots ankle length with a midi dress or go with a thigh-high option. Because midi skirts end at the shin, your footwear needs to fall below or above that area to look flattering.

PiePieBuy Women’s Tie Knot Chelsea Ankle Boots

Here we have a pair of ankle-length Chelsea boots from PiePieBuy to try out. These boots are faux suede, have a synthetic sole, and come in a few different colors.

View these ankle boots on Amazon here.

Shoe’N Tale Women Stretch Suede Thigh High Boots

Here is another pair of boots to try with a midi skirt from Shoe’N Tale. These boots are 100% suede, have a rubber sole, and are 3.5 inches high.

Follow this link to view these on Amazon.

Are Ankle Boots Flattering?

When it comes to ankle boots being flattering, we say yes. Typically, ankle-length boots cut off slightly above your ankle, so they aren’t uncomfortable to wear. Like we mentioned earlier, heeled ankle boots have a stylish look to them and flatter a midi skirt or dress. Of course, this does come down to you, but overall we would agree that ankle boots are relatively flattering.

What Should You Not Wear With Ankle Boots?

Now that you know what does go with ankle boots, there are a few things to avoid. Typically, we suggest staying away from short skirts or pants, high socks, and super short dresses. Although these styles look good on their own, ankle boots tend to look awkward when paired with them.

A good fashion rule to follow is either a short-cut shoe and mid to long-length skirt/pants or vice versa. When you pair too many cropped or short things together, you can create an incomplete-looking outfit without even knowing.

Can I Wear Ankle Boots All Year?

For anyone debating the proper season for ankle boots, we think you can wear them year-round. Whether it’s summer or winter, ankle boots are a more comfortable alternative to heels and go with plenty of outfits. As long as you style the rest of your outfit according to the season, we see no problem with wearing ankle boots whenever you want to.

Soda Glove Chunky Heel Ankle Boot

Here is a good year-round pair of ankle boots from Soda to try. These chunky heel boots are suede and faux leather, 3.5 inches tall, and comes in a few different colors.

View these ankle boots on Amazon here.

What Shoes Do You Wear With A Midi Skirt In The Winter?

When it comes to wintertime footwear with a midi skirt, we suggest something warm and comfortable. Like we mentioned, boots, sneakers, and even heels are good options for the winter months. Generally, try to dress your skirt up rather than more casually in the winter with a pair of fashionable shoes. Regardless of what your style is, a platform or heel of some kind will go best with a midi skirt during the winter.

ICHIGO Women’s Fashion Ankle Booties

Here we have a pair of ankle-cut combat boots from ICHIGO to wear in the winter. These boots are synthetic leather, lightweight, and have a non-skid outsole.

See these combat boots on Amazon here.

PUMA Women’s Smash Platform Sneaker

Here is another shoe to try with a midi skirt in the winter from Puma. These platform sneakers are fabric and synthetic material, have a rubber sole, and come in various colors.

Check these sneakers out on Amazon here.

Jessica Simpson Women’s Parisah Platform Pump

Here we have another wintertime shoe idea from Jessica Simpson. These platform pumps are imported, have a synthetic sole, and come in many fun colors and patterns.

Follow this link to see them on Amazon.

Are Midi Skirts Good For The Winter?

Like any skirt or dress, a midi style is fine to wear in the winter. With that said, midi skirts are not very warm, and you might want to layer your clothing. From what we saw, tights or leggings during the winter are a great idea to try under a midi skirt or dress. As long as you feel warm and comfortable, we say layer up or down to your liking.

VERO MONTE Womens Opaque Warm Fleece Lined Tights

Here we have a pair of fleece-lined opaque tights from Vero Monte. These tights are polyester and spandex, snugly fit your legs, and come in a few color options.

See these tights on Amazon here.

Are Midi Skirts In Style?

Horizontal cropped image of stylish slim woman in beautiful yellow skirt

Although everyone has a different opinion, midi skirts are trendy among both young and mature shoppers. When it comes to if they are “in style,” we say they are. Midi skirts are the perfect compromise for anyone not wanting to wear a maxi skirt or something too short.

Even with their mid-shin cut-off, midi skirts are a great year-round option and are very comfortable. We recommend trying one if you haven’t and seeing how it makes you feel.

Are Midi Skirts Considered Business Casual?

If you want to wear a midi skirt to work, we think that is a great idea. Although this style can go either way, you can class it up with a button-down shirt or blouse and a pair of sensible shoes. Regardless of where you are off to, styling can make a huge difference in how your skirt ends up looking.

Amazon Essentials Women’s Pull-on Knit Midi Skirt

Here is a pull-on midi skirt from Amazon Essentials that is business casual. This skirt is rayon and spandex, machine washable, and comes in a variety of colors.

View this skirt on Amazon here.

SheIn Women’s Casual Side Bow Tie Blouse

Here is a blouse from SheIn that you can wear with a midi skirt to the office. This blouse is 100% polyester, drawstring closure, and comes in many different colors and patterns.

See this blouse on Amazon here.

Our Final Thoughts

Whether you frequently wear a midi skirt or dress with ankle boots or never thought to try it, it’s an option to consider. From what we found, midi styles go well with ankle boots, heels, and even sneakers. Although this style of skirt and dress cuts off near the shin, a platform or heel can make a world of difference. We especially love the grungier combat boot look for wintertime and then a heeled ankle boot in the summer. Regardless of what you choose, make sure to pick comfortable footwear and have some fun with your styling.

Want to read more? Head over to these super helpful related posts!

How Long Is A Midi Skirt Or Dress?

What Can You Wear With Midi Skirts? [11 Outfit Ideas]

How To Hem A Pleated Skirt [Even Without Sewing!]

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