Your Complete Guide to What Shoes To Wear With Midi Skirts in Winter

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Wondering how you can still wear your favorite midi skirts even in winter, in this midi skirt footwear guide I am sharing best shoes that you can pair with your midi skirts, chic midi skirt and shoes combos and still stay comfortable in the cold winter.

I myself have fallen into the habit of just wearing jeans or pants in winter where it gets really boring and you feel like you are wearing the same outfits over and over again. But when you have versatile bottoms like skirts that you style properly, you maximize your wardrobe throughout the year and not just for seasonal wear. 

When you are headed to a holiday party and you suddenly feel like you don’t have anything to wear, you know what is going to come to your rescue? Skirts. Now that I have convinced you to keep your skirts on your rack even in winter, lets get into the fun stuff, best shoes styles that you can wear with midi skirts. 

What's Covered In The Post

Tiered Midi Skirts

There are two styles of tiered midi skirts you would see out there, tiered stitched Midi skirt and Tiered Layer Midi skirt. 

Tiered Stitched Midi Skirt

This is one of the toughest style of midi skirts that can cut you off in weird places and make you look frumpy if paired with wrong footwear. 

But you can pair them with pointed toe ankle boots that will elongate your feet and make you look taller as well. These skirts are also amazing with tall boots with pointed front. Yes, pointed toe is the mantra here. The skirt itself is free flowing but is also sticked and cut in places that does not create flattering line. By wearing shoes that look leaner and have a silhouette to them, it adds some structure to your outfit.

If you feel like you like you are want to stay warmer, you can always add skin color tights or black tights if you are wearing black boots. 

What Shoes To Wear With Midi Skirt in Winter

Tall Boots

They will cover your legs and make you look taller since there is a single line. The heels also give you some height.

SAM EDELMAN Annabel Tall Western Boots

White Block Heel Ankle Boots

Pair them with some Fleece nude tights and you will look chic and stylish. 

Black Ankle Boots

Pair them with black tights and you will have legs for days. The pointy toe looks chic and stylish.

Tiered Layered Midi Skirt

This style of skirt is perfect for cold weather because it naturally adds more curves to your bottom half and you instantly get the hourglass look. But you need to keep that style going with these skirts with the right footwear. 

Huggable ankle boots that have a side zip, or sock boots that completely hug your ankles would look perfect with these styles of skirts. This skirt style is more dressed up, so the shoes need to do that too. 

You can also wear tall boots, but make sure that they are not too wide around calf, because your legs would look really thick with these boots. And if they have some sort of heel, mostly block heel, they will look perfect.

Black Sock Ankle Boots

The sock style hugs your ankle and makes the look lean. You can pair these with black tights to keep yourself cozy.

Black Tall Boots

These boots are narrow calf so they don’t make you look bulky under all those layers.

FRANCO SARTO Katherine High Shaft Boots

Colored Kitten Heeled Ankle Boots

This is a great opportunity to wear some colorful boots to match your skirt. And burgundy is a great shade that goes with red and other colors.

Alfani Dress Booties In Burgundy

Pleated Midi Skirts

Plain Pleated Midi Skirt

Almost all of us have a version of a plain midi skirt, it can be black, white or colored. You can also wear it in cold weather. 

My go to shoes would be Chelsea boots with them that have slight block heel to elongate your legs. Chelsea boots are usually pointed in style, but they are also minimal looking boots and look professional as well. You can also wear suede boots that have pointed heels to create a formal look with these skirts. 

If you wear tall boots then your legs would look bulky. The slim A line style of the skirt will emphasize the wide calf boots and make your legs look thicker. You can avoid that by wearing tights and ankle boots with these.

You can also wear heeled loafers with these skirts that can add some detail to your outfit and elevate your look. Don’t forget to wear tights to keep you warm, if you don’t want to wear tights, you can wear long socks as well. 

White Chelsea Boots

White Chelsea boots would look give structure and add to your work look. But they will make it more fun and wearable.

Everlane The Glove Boot

White Heeled Loafers

These instantly elevate your whole outfit with the gold hardware details. But they are also super comfortable to wear.

Sam Edelman BLOCK HEEL LOAFER

Tall Light Colored Boots Boots

If you are not a fan of white boots you can also pick neutral tone boots that would look great with black or colored pleated midi skirts.

NATURALIZER Waylon High Shaft Boots

Printed Pleated Midi Skirt

This is my favorite style of pleated skirt because the prints give them some more character and you can easily pair them with so many colors of tops because of the prints. 

You can wear tall boots with this style of midi skirt because the prints are already distracting your eyes. I would either wear a contrasting color tall boots, or I would pick black tall boots. But in both cases they need to have some sort of heel and no round toe. Otherwise you will look frumpy and short. 

You can also wear ankle boots as well, but these skirts call for Brogues as well. So, if you own some, then you can create a feminine and masculine style balance. You can also wear loafers and oxfords that create the same style as brogues. 

Tall Light Colored Boots Boots

Whether you have a dark tone or lighter tone printed skirt, you can still rock these nude tall boots with them.

NATURALIZER Waylon High Shaft Boots

White Heeled Loafers

Since these are structured shoes you can wear them with the printed pleated midi skirt too. Add some nude tights and you are rocking.

Sam Edelman BLOCK HEEL LOAFER

White Heeled Loafers

Pointed heel black ankle boots are an essential and they complete your workwear look for winter with these skirts.

Brogues or Oxford heels

These have made a major come backs and look so chic worn with a more structured yet romantic looking skirt.

Leather Midi Skirts

Full Leather Midi Skirt

If you are think of boots, ankle boots would be perfect for this, since Tall boots would make you look frumpy because of the flowy style of the skirt. But you can also wear pumps, slingback pumps and loafers with these style of skirts. 

Usually you could wrap a belted around these styles of skirts or they come with belts, so finishing them with shoes that look more put together always elevates your outfit. 

You can also wear ballerina flats that will create a minimal sophisticated look.

Leather or faux leather skirts would keep you warm, so you can get away with wearing shoes that show some ankle. But if you still want to wear boots, sock style ankle boots would be great. 

And you can add more coziness with skin color tights. 

Full Leather Midi Skirt​

Kitten Heeled Ankle Boots

The kitten heels are a really comfy version of heels you can wear, but the sock style booties will make your legs look leaner.

Ballerina Flats

You can totally wear flats in winter too. Just wear nude fleece lined tights to keep yourself warm and cozy.

AGL Lolita Flat

Black Loafers

Another favorite style of flats for winter are loafers. These sleek and long ones look feminine and stylish.

Pleated Leather Midi Skirt

This is another versatile fall, winter and spring skirt that you can style in so many ways and can pair so many styles of shoes as well. My only catch is that avoid shoes that are as shiny as the skirt, because then they look tacky and make your outfit look cheap. 

I would go with suede ankle boots that tone down the shininess and make you look put together. You can also wear colored or white loafers which will not be as shiny as black one. 

You will love me for this, you can also wear white leather sneakers with them to create a casual yet stylish outfit. This way you stay cozy and look effortlessly stylish as well. 

Some other good shoes are ballerina flats and pumps

White Leather Sneakers

Leather or Faux leather makes it easier to wear shoes that are not boots. I love wearing white leather sneakers with leather skirts that tone it down without making it boring.

White Loafers

If you are wearing pleated leather midi skirts, you can easily create a contrast with white loafers and make them look sophisticated.

Black Suede Ankle Boots

If you are going for boots, you should pick ankle boots instead of tall boots that can make you look bulky. And since the faux leather would look shiny, picking suede will balance it out.

SAM EDELMAN Women's Fawn Block-Heel Booties

Satin Midi Skirts

Satin Bias Midi Skirt

One of the most popular style of skirts and perfect for holiday parties or date nights, but really hard to stay warm in cold weather. I would not recommend wearing this if you live somewhere its extremely cold.

But if you want to wear it, I recommend wearing sock ankle boots that keep the lean style of the midi skirt and keep you looking lean. This is where you want to wear some shape wear not with the exact purpose of keeping you looking slim, but to add another layer underneath your legs and avoid sweater bulking up, because you can tuck that in the shape wear. 

But I love wearing pumps and pointed heeled booties that show a lot of ankle skin and are perfect for occasion wear. Want to wear it casually, go for white leather sneakers.

Satin Bias Midi Skirt

Kitten Heeled Ankle Boots

Since this skirt I narrow wearing bulky boots are not a good idea. Pick these sock style ankle boots with kitten heels.

White Leather Sneakers

White leather sneakers will keep your feet cozy and will make this midi skirt wearable for everyday. To make it cozy, don’t forget to wear nude fleece lined tights.

Nude Block Heel Pumps

Block heels are really comfortable and these nude pumps will add some structure to the satin bias midi skirt.

Satin Full Midi Skirt

This style of skirt is more giving and you can wear tights under it as well. But I still like wearing nude colored tights because they are invisible and it appears that you are still showing your ankles. 

You can easily wear ankle boots, but grab those kitten heels or pointed heels that will look put together with skirt. You can also wear pumps or close toe mules. 

The key is again making sure that you are not wearing shiny footwear since the skirt itself is shiny. But if you are wearing leather, the go for tan or nude ankle boots. Or go for suede footwear or even white ones. 

If you want to wear flat, loafers would look really amazing with the satin skirt. It will elevate the outfit and keep you comfortable.

Black Loafers

These are perfect flats with this flow satin midi skirt to create more structure and a great way tp tone it down. Don’t forget to wears her nude tights.

Chelsea Booties

These are low ankle booties and look really feminine yet structures. This will make your ankles look lean and stylish.

BANDOLINO Women's Gallo Dress Booties

White Ankle Boots

White boots are my favorite because they look great with any outfit and make it look really expensive. These boots will do just that with to your skirt.

BANDOLINO Women's Grilly Dress Booties in white

Suede Midi Skirts

These styles of skirts are opposite to the satin or leather skirts. They have a matte shin to them, but they usually look way more expensive and rich because of the sueded texture.

Suede Full Midi Skirt

Since the suede is always subtle, you can wear tall boots and ankle boots with them. The flare style of the skirt looks really flattering on any body type and you can get away with a lot of style of boots. 

But I would still avoid flat chunky boots because they will bring your outfit with this skirt down. 

If you want to add some edginess to your look, you can wear heeled lace up boots. But the important part is that they need to have some heels. 

Other than boots you can wear flat loafers, heeled loafers, pumps and also ballerina flats. Suede material will keep you warm, but if you want to layer up, add long songs that stay hidden under the skirt.

Suede Full Midi Skirt

Black Loafers

You can wear flats easily with this style of midi skirt. Loafers will elevate your outfit even if you are wearing simple sweater. 

White Heeled Loafers

These would look chic and dressy with the suede full midi skirt. So, if you are headed for a classy party, you can totally wear these.

Sam Edelman BLOCK HEEL LOAFER

Black Tall Boots

Tall boots would also look great with these skirts as they have a fuller style. I love contrasting tall boots, but your safest bet would be black ones. 

FRANCO SARTO Katherine High Shaft Boots

Pencil Midi Skirts

You can also wear pencil skirts in winter too. And I am sharing 3 different styles of pencil skirts I see a lot and what shoes you can wear with them in winter. 

Back Slit Pencil Skirt

This is a really formal style of skirt, but you can have some fun with it too. The perfect winter shoes with the back slit pencil skirts are pointed heel ankle boots which instantly elevates the outfit. And I would either wear black or nude to compliment the skirt and not make my shoes stand out. 

And the awesome part is that you can wear tights under these skirts which will make it even more flattering. So you can wear heeled loafers, or pumps

If you want to wear these pencil skirts casually for winter, I would wear them with white leather sneakers and oversized sweater. That outfit combination is so chic and looks effortless too. 

Back Slit Pencil Skirt

Black Ankle Boots

Heeled black ankle boots would look great with pencil midi skirts because they will elongate your legs.

SAM EDELMAN Women's Fawn Block-Heel Booties

White Leather Sneakers

Sneakers are really common to wear with pencil midi skirts to make them look casual, but if you pick white leather sneakers, your outfit will be next level.

Nude Pumps

You can also wear pumps in winter. Just pair it with some nude tights to stay cozy and comfortable. 

Side Slit Pencil Skirt

I love this style of midi skirts, they are comfortable and stylish and perfect for special occasion. And they are also easy to pair different shoes with. 

You can wear tall boots and ankle boots with them. But if you are wearing leather skirt, then pick suede boots and vice versa. 

This is a style of skirt which will also look good with fitted tall boots that go above thighs. But they look good for night out looks. So, I will be careful where I wear them to. 

If you don’t want to wear boots, you can wear ballerina flats to create a minimalistic look. And wear leather sneakers to create a casual look even in winter. You can also add tights to stay cozy if the fabric of the skirt is too light.

Side Slit Pencil Skirt​

Over The Knee Boots

These styles of midi skirts are perfect to wear for special occasion and wearing over the boots will make you look glamorous.

MARC FISHER Women's Reda Over The Knee Boots

Chelsea Booties

These low ankle booties will also look great with the leather pencil skirts since they will not make your ankle look bulky.

BANDOLINO Women's Gallo Dress Booties

Ballerina Flats

Ballerina flats are one of my favorites to wear with pencil skirts. You look so elegant in them. Just add some nude fleece lined tights.

AGL Lolita Flat

Sweater Midi Skirts

This is perfect style of skirt for fall and winter because they are really cozy and comfortable. They come in a lot of style most of which I have covered, but the most popular style is a fit and flare style of midi skirt which you will almost find everywhere.

Fit n Flare Sweater Midi Skirt

Since the skirt is woolen already, you don’t really need to wear tights underneath. You can just pair it with heeled ankle boots to create a dressy outfit. You can also add tall narrow calf boots to stay cozy and look stylish as well. I will avoid wide calf tall boots or loose boots that fold up. 

But if you are on the skinny side, you might get away with that. 

You can easily wear all your fall footwear with this style of skirt and look chic. Some of them are Loafers, heeled mules, slingback pumps

Because these skirts are so cozy you can easily get away with not wearing tights to cover you legs. 

Black Ankle Boots

These skirts are fuller in with and you can easily get away with wearing black ankle boots, no matter what color of the skirt is.

SAM EDELMAN Women's Fawn Block-Heel Booties

Heeled Loafers

These not only look stylish with the sweater skirt, you will not feel too hot in them since sweater skirts do make you feel cozy.

Sam Edelman BLOCK HEEL LOAFER

Tall Nude Boots

These boots look stylish and because they are nude they balance out the colors of the sweater skirt.

NATURALIZER Waylon High Shaft Boots

How To Stay Cozy With Midi Skirt

The biggest reason most of us skip wearing skirts is because we want to stay cozy and skirts expose our legs and it gets cold and uncomfortable for us. But then, you can’t just wear black tights and call it a day, because Midi skirts fall in the middle of your feet and knee, so its hard to find the right balance. 

Your first friend are nude tights that will keep you cozy but will look like you have exposed skin. This will work with most styles of midi skirt. 

But did you know you don’t have to wear tights always. You can also wear, thigh high socks while wearing tall boots or match the color of the boots so, it looks like you are wearing tights but you are not. 

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Midi Skirts to Avoid Wearing in Winter

Yes, there are a few midi skirts that you should put away because they just feel out of season and frumpy when you try to wear them in winter. 

  • Denim skirts – These skirts are great maybe for spring and definitely for summer.
  • Wrap skirts – I have to say, this is a personal opinion, but these are the clumsiest skirts and honestly we all should stop wearing them because who has time to fix their skirt every 30 minutes. 
  • Linen Skirts – These are lightweight and are meant to be for summer. 

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