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20+ Best Shoes To Wear With Midi Skirts [2024] & Chic Outfit Ideas To Copy

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Are you wondering what shoes to wear with midi skirts? Check this post for how to wear a midi skirt, and the best shoes to wear with a midi skirt for stylish outfit ideas this year!

Midi skirts are a staple in any woman’s wardrobe; they can be dressed up or down, making this skirt style perfect for any occasion.

But, the right shoe is essential to complete the perfect look.

From statement heels to comfy flats, there are plenty of options to choose from when looking for the best shoes to pair with midi skirts.

In this article, we will cover 20 of the best shoes that you can easily style with midi skirts for a chic, stylish look.

collage of the best shoes to wear with midi skirts

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This post is all about the best shoes to wear with midi skirts.


What Shoes Can I Wear With A Midi Skirt?

There are plenty of shoe options out there that you can wear with a midi skirt, from sneakers to heels and everything in between.

One option that’s been trending lately is wearing ankle boots with a midi skirt.

Ankle boots add an edgy touch to your look and come in various styles such as suede, leather or snake print.

If you’re looking for something more casual, then sneakers might be the way to go.

Sneakers have become a staple in everyone’s wardrobe and they’re perfect for dressing down a midi skirt for a more relaxed look.

You can opt for classic white sneakers or experiment with bold prints and colors.

Another great option is sandals which are perfect for summertime outfits.

Sandals give off a bohemian vibe while still being comfortable enough for all-day wear.

Lastly, if you’re aiming for something more formal, then heels should be your go-to choice.

Heels elevate any outfit and make you feel confident and powerful.

Whether it’s stilettos or block-heeled pumps, find the right pair that complements your style and personality best!

Now scroll on to check our favorite shoes to wear with a midi skirt for a stylish look.


Best Shoes To Wear With Midi Skirts



Sneakers are the perfect shoe option to wear well with midi skirts for a casual and comfortable look.

Whether you opt for classic white sneakers or bold-colored ones, they will make your outfit look effortlessly chic.

White sneakers, in particular, have been a fashion staple for years and pair beautifully with any color midi skirt.

For a more elevated take on this trend, try pairing high-top sneakers with your midi skirt.

This look is perfect if you’re going for an edgier vibe or want to add some height to your ensemble.

You can also choose metallic or glittery sneakers to add some sparkle and shine to your outfit.

Lastly, consider slipping into slip-on sneakers if you’re looking for a quick and easy solution that still looks stylish.

They come in various prints and textures that can elevate any plain midi skirt outfit.


Flat Sandals

Flat sandals are the perfect complement to a midi skirt for a casual yet chic look.

With so many styles available, it’s easy to find a pair that fits your personal style and matches the occasion.

A simple pair of leather or suede flat sandals can elevate an outfit while still keeping you comfortable throughout the day.

For those who want to add some extra flair to their outfit, there are plenty of embellished and patterned flat sandal options available.

From beaded designs to colorful prints, these sandals can add a pop of personality to any midi skirt ensemble.

When styling flat sandals with midi skirts, it’s important to consider proportions.

Opt for sandals with slim straps or minimal design elements so they don’t overpower the flowy silhouette of the skirt.

Additionally, choosing a sandal in a neutral color can help elongate your legs and create a more streamlined look overall.



Loafers are a versatile shoe style that can be dressed up or down to create a variety of chic outfits.

For a sophisticated look, pair classic leather loafers with a midi skirt and blouse.

The loafers add an element of refinement to the outfit while still being comfortable enough for all-day wear.

For a more casual outfit, opt for suede or velvet loafers in a bright color or pattern.

These can be paired with a simple t-shirt and denim midi skirt for an effortlessly stylish look.

Loafers also work well with cropped pants or culottes, adding an element of sophistication to these trendy styles.

When choosing loafers to wear with midi skirts, consider the material and color carefully.

Patent leather or metallic finishes add shine and texture to an outfit, while neutral colors like black, brown, and navy provide versatility and can be worn with almost anything in your closet.


Mary Janes

One shoe style that never fails to add a vintage touch to an outfit is Mary Janes.

These classic shoes have been around for over a century and have remained popular throughout the years.

Mary Janes are defined by their low-cut design and elegant strap that fastens across the top of the foot.

They can be found in various heel heights, from flat to high heels, making them versatile enough for any occasion.

For a casual look, pair black Mary Janes with a flowy floral midi skirt and a white blouse tucked in.

Add some gold hoop earrings for an extra touch of glamour.

For a more formal event, opt for patent leather or suede Mary Jane heels in deep jewel tones like emerald green or sapphire blue.

Pair these statement shoes with a simple black midi skirt and fitted blazer for an effortlessly chic look.

Whether you’re going for a retro vibe or just want to add some feminine flair to your outfit, Mary Janes are sure to elevate any midi-skirt ensemble.


Ankle Boots / Chelsea Boots

Ankle boots and Chelsea boots are both excellent choices to wear with midi skirts.

They are versatile, stylish, and can be dressed up or down depending on the occasion.

Ankle boots typically have a heel height of 2-4 inches, while Chelsea boots have a more uniform look with their signature elastic side panels.

If you’re looking for a shoe that’s easy to slip on and off, then Chelsea boots would be a perfect choice.

They come in various materials such as leather or suede, making them ideal for colder weather.

The sleek design complements the flowy silhouette of midi skirts perfectly.

Ankle boots, on the other hand, offer more variety in terms of style and length.

You can wear black ankle boots with pointed toes for a more sophisticated look or go for Western-inspired styles with chunky heels to add some edge to your outfit.

Whatever your preference may be, ankle boots will elevate any midi skirt ensemble effortlessly.


Tall Boots / Knee-High Boots

Tall boots, including knee-high boots and over-the-knee boots, are one of the best shoes to wear with midi length skirts.

They add an extra layer of warmth in cooler weather and provide a sleek and sophisticated look.

When choosing tall boots to pair with midi skirts, it’s important to consider the height of the skirt and where it falls on your leg.

Knee-high boots work well with mid-length skirts that fall just above or below the knee.

One popular way to wear tall boots with midi skirts is by pairing them with oversized sweaters or chunky knit tops.

This creates a cozy yet chic look that’s perfect for fall and winter.

For a more polished outfit, try wearing knee-high boots with a tailored blazer or blouse tucked into your skirt.

Accessorize with statement jewelry and a clutch for added glamour.

When it comes to color choices, black or brown leather knee-high boots are classic options that will never go out of style.

However, don’t be afraid to experiment with bold colors like burgundy or navy blue for an unexpected pop of color in your outfit.


Combat Boots

Combat boots are a versatile and stylish choice to wear with midi skirts.

They add an edgy touch to your outfit and are perfect for fall or winter weather.

Pair them with a flowy midi skirt and a sweater for a cozy yet chic look, or go for a more daring approach by pairing them with a leather midi skirt for an elevated grunge look.

When it comes to choosing the right pair of combat boots, opt for those that have good traction and support.

Look for styles with thick soles and sturdy laces or buckles that can withstand daily wear.

For added comfort, choose boots that have cushioned insoles or memory foam padding.

Overall, combat boots are the perfect addition to any wardrobe looking to add edge and personality to their outfits.

Whether you prefer classic black leather or bold colored options, there is no doubt that these shoes will become your new go-to option when styling midi skirts this season!


Cowboy Boots

Cowboy boots have been a fashion staple for decades, and they are still going strong.

These versatile shoes can be paired with midi skirts for an effortlessly chic look.

Whether you’re going for a casual or dressed-up style, cowboy boots can add some Western flair to your outfit.

When it comes to selecting the right pair of cowboy boots to wear with midi skirts, there are a few things to consider.

First, think about the color and material of the boots. If you want a classic look, go for brown leather boots.

If you prefer something more daring, try black or colored suede options.

Another important factor when wearing cowboy boots with midi skirts is the style of the skirt itself.

A-line or full-circle midi skirts work best with this type of footwear as they balance out the wide silhouette of the boot shaft.

Whether you opt for denim or leather cowboy boots and pair them up with a pleated skirt or wrap-style patterned one; make sure you choose what looks best on your body type and personal taste so that you feel confident in your outfit all day long!


High Heels / Kitten Heels


High heels are a classic choice when it comes to pairing them with midi skirts.

With the right height and style, they can make your legs look longer and add a touch of sophistication to your outfit.

However, it’s important to choose comfortable high heels that won’t leave you limping at the end of the day.

One popular option is kitten heels, which are typically around 1-2 inches in height.

They provide just enough lift to elongate your legs without sacrificing comfort.

Another stylish yet practical choice is block heels, which offer stability and support while still looking chic.

Opt for a pair in a neutral color like black or nude so that they can easily be paired with any midi skirt.

If you’re feeling daring, style your midi skirt with high heel mules for an edgier look.

These slip-on shoes have no back or straps and expose most of the foot, making them perfect for warmer weather.

Just be sure to practice walking in them before venturing out as they can take some getting used to!


Strappy Sandals

Strappy sandals are the perfect addition to any midi skirt outfit. With their delicate straps and minimalist design, they add a touch of elegance and femininity to your look.

Whether you opt for a basic black or brown pair or choose a more colorful option, strappy sandals will make your feet look chic and stylish.

To really make your strappy sandals stand out, consider pairing them with a midi skirt in a bold print or bright color.

This will draw attention to both your feet and your skirt, creating an eye-catching ensemble that is sure to turn heads.

For those who prefer a more subdued look, opt for neutral tones like beige, nude, or white which will complement any outfit effortlessly.

When it comes to accessorizing with strappy sandals and midi skirts, less is definitely more.

These shoes speak for themselves and don’t require much embellishment or flashy jewelry.

Keep it simple with some dainty earrings or bracelets to complete the look without overpowering the style of the sandal itself.


Chunky Shoes


Chunky shoes are a great way to add some edginess and personality to any midi skirt outfit.

These shoes come in various styles such as platform sneakers, combat boots, and even clogs.

They not only provide comfort but also add height, giving the illusion of longer legs.

Pairing chunky shoes with midi skirts creates an unexpected contrast that instantly elevates your look.

It’s important to balance out the bulkiness of the shoes with a more fitted top or slim-fitting bottom.

For example, you can wear a cropped sweater with an A-line midi skirt and chunky platform sneakers for a casual yet chic outfit.

Overall, chunky shoes are versatile footwear that can be worn on various occasions and seasons.

They add character to any outfit while providing comfort and support for your feet throughout the day.

So don’t be afraid to experiment with different styles of chunky shoes!


What Shoes To Wear With A Midi Pencil Skirt?

When it comes to pairing shoes with a midi pencil skirt, the options are endless.

Depending on the occasion and your personal style, you can wear flats, heels, or even sneakers.

For a sophisticated and elegant look, heels are always a great option. Pointed-toe pumps or strappy sandals add a touch of glamour to any outfit and elongate your legs when paired with a midi skirt.

If you’re looking for something more casual yet still chic, flats can be a great choice.

Ballet flats or loafers in neutral shades like black, beige or nude will complement any color of the midi skirt while keeping you comfortable throughout the day.

For an edgier look, try pairing your midi pencil skirt with ankle boots or combat boots.

Sneakers are not only comfortable to wear but also trendy at the moment.

Pairing them up with a midi pencil skirt creates an interesting contrast between feminine and sporty styles that will leave you feeling confident as well as stylish all day long!


What Shoes To Wear With A Midi A-line Skirt?

When it comes to pairing shoes with a midi A-line skirt, there are several options to choose from.

One of the most popular choices is ankle boots. Ankle boots are versatile and can be styled in various ways, whether you opt for a flat or heeled version.

If you’re looking for something more casual, then a pair of sneakers or flats can also work well with an A-line midi skirt.

Another great option would be pumps or heels. These elongate your legs and add some height to your overall look.

However, if you’re not comfortable wearing high heels all day long, then try kitten heels instead.

Kitten heels provide the same amount of height as stilettos but without the discomfort of walking in them all day long.

Lastly, sandals can also pair well with a midi A-line skirt during the summer months.

Opt for strappy sandals that complement the color palette of your outfit while adding some visual interest to it at the same time.

Whether you prefer flats or heels, remember that comfort should always come first when choosing shoes to wear with a midi A-line skirt!


What Shoes To Wear With A Pleated Midi Skirt?

Pleated midi skirts have been a go-to style for many women over the years.

The versatility of the skirt makes it easy to dress up or down, depending on the occasion.

When it comes to choosing shoes to wear with a pleated midi skirt, there are plenty of options available that can elevate your outfit and make you look stylish.

One classic shoe option that pairs perfectly with a pleated midi skirt is pumps.

Whether you opt for neutral shades or bright colors, pumps can give your outfit a sophisticated look.

Another shoe style that looks great with pleated midi skirts is ankle boots.

They add an edgy touch and provide coverage during colder weather.

If you’re looking for something more casual, sneakers are a great option too.

They add comfort and practicality while still being chic enough for everyday wear.

Additionally, sandals can also work well in warmer weather, providing a relaxed and effortless vibe to any outfit combination involving a pleated midi skirt.


What Shoes To Wear With A Midi Denim Skirt?

When it comes to styling a midi denim skirt, the right pair of shoes can make or break your entire outfit.

Whether you’re going for a casual or dressy look, there are plenty of shoe options that can elevate your style game.

Here are some top picks for shoes to wear with a midi denim skirt:

1. Sneakers: For a laid-back and comfortable vibe, pair your midi denim skirt with white sneakers.

2. Ankle Boots: When the weather starts to cool down, ankle boots paired with a midi denim skirt are perfect.

3. Strappy Sandals: If you want to dress up your outfit and show off some skin, strappy sandals are an excellent choice.

4. Loafers: Loafers can add a touch of sophistication and classiness to any outfit – including one featuring a midi denim skirt.

5. Wedges: For an ultra-feminine look, try pairing your midi denim skirt with some wedges – it’ll elongate your legs and complete the look perfectly.

All in all, choosing the right shoes for your midi denim skirt depends on what kind of vibe you’re going for – but with these suggestions in mind, you’re sure to turn heads no matter what!


What Shoes To Wear With A Midi Tulle Skirt?

When it comes to pairing shoes with a midi tulle skirt, there are a few things to consider.

Firstly, the skirt length should be taken into account. Ideally, you want your chosen footwear to complement and not overpower the skirt.

Secondly, the occasion and overall style of your outfit are also important in determining what shoes will work best.

For a casual daytime look, sandals or sneakers can add a touch of playfulness to an otherwise feminine midi tulle skirt.

A pair of classic white sneakers or strappy minimalistic sandals can create a chic yet effortless look.

For cooler weather or more formal occasions, opt for ankle boots or pumps that will elevate your outfit.

When it comes to colors and patterns, solid-colored shoes in neutral tones like black, beige, brown, or white would work well with most midi tulle skirts.

However, if you want to add some personality to your outfit, you can experiment with bold colors or prints that match other pieces in your ensembles such as a blouse or accessory.

Ultimately though, comfort is key when choosing shoes for any occasion – make sure you choose footwear that feels good on your feet!


What Shoes To Wear With A Midi Skirt In Fall And Winter?

When it comes to styling a midi skirt in the fall and winter months, choosing the right shoes can make or break your outfit.

The key is to find footwear that not only complements the length and style of your skirt but also keeps you warm and comfortable in cooler temperatures.

For a classic look, ankle boots are a popular choice. Opt for a sleek leather or suede pair in black or brown to create an effortless, chic ensemble.

For added warmth, choose boots with fur lining or chunky soles for better traction on slippery surfaces.

If you’re looking for something more playful, try pairing your midi skirt with sneakers.

This unexpected combination adds an edgy touch while still keeping things casual and comfortable.

Choose from classic white kicks or bold statement sneakers to create a unique look that reflects your personal style.

Lastly, if you want to elevate your outfit even further, wear midi skirts with heeled boots or pumps.

These styles can instantly dress up any look while elongating your legs and adding femininity to the overall aesthetic.

Choose neutral colors like black boots or white boots for versatility or experiment with bold hues like red or burgundy for a pop of color that will surely turn heads.

Wear tights together with your favorite shoes to add warmth.


How Do You Wear A Midi Skirt Without Looking Frumpy?

When it comes to styling your favorite midi skirt, the key is balance.

To avoid looking frumpy, it’s important to find a balance between femininity and structure.

One way to achieve this is by pairing a flowy midi skirt with a fitted top or blazer.

This will create a definition at the waistline and give your outfit some shape.

Another tip is to choose the right shoes. Midi skirts look great with various types of footwear but choosing the wrong ones can make you look frumpy.

For instance, chunky sneakers or flat sandals can weigh down your outfit, whereas heels or ankle boots can elevate it.

Lastly, don’t be afraid to experiment with layers and accessories.

A denim jacket or leather moto jacket over a midi skirt adds an edgy touch while statement jewelry can add interest to a simple outfit.

When done right, wearing a midi skirt can be both comfortable and stylish!

This post was all about the best shoes to wear with midi skirts.


About The Author

Tracy is an experienced personal stylist, shopping expert, and fashion & lifestyle blogger. She has been featured on Time Magazine, Bustle, Best Life, Glam, The Zoe Report, Mic, and GOBankingRates, for her insights on fashion, beauty, home decor, and lifestyle. Read More


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