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Do’s & Dont’s of Wearing Midi Skirts with Ankle Boots & Styling Ideas

Do’s & Dont’s of Wearing Midi Skirts with Ankle Boots & Styling Ideas


Do's & Dont's of Wearing Midi Skirts with Ankle Boots & Styling Ideas

As I get older, I have realized the benefits of wearing midi skirts and they can be really fun with ankle boots for the colder months. In this post I want to share some easy guidelines you can follow when you pair both of them together to create an effortless chic outfit. There are two things that we always want to achieve when we get dressed and which is the essence of style:

  • An Outfit That Flatters our body.
  • The Outfit Also Elevates our personality.

These are the main reason we essentially want to style our looks for anything. And hopefully, by the end of this post you will find that you can do that easily when you wear midi skirts with ankle boots.

How to Not Look Short

Midi skirts lengths often make us look shorter than we are, and if you wear ankle boots that cut you off at the ankle, it just makes the situation worse. Unless you are really tall in which case, you should not care at all. 

There are few ways you can style your midi skirts with ankle boots that make you look taller. 

My favorite way is to wear monochrome, but match the color of your skirt with the color of the boots. This is really easy to achieve with black, white, brown and neutral colors. When you wear a monochrome outfit, the eyes naturally pay attention to the color that is visible or appears more in the whole look. This creates a cohesiveness to the eyes and even though your ankle boots are cutting your legs abruptly which is the main reason for looking shorter in ankle boots and midi skirts. 

But with this trick will always ensure that eyes are not focusing on the word gap between your legs caused by the midi length of the skirt and the short boots.

Another trick that I use is to pick midi skirts that don’t end at mid calf. Yes, this means that midi skirts that are a bit longer than mid calf actually have a way of making you look taller in them. And even if you pick low ankle boots, the gap between the skirts and the boots is not that much which in turn helps elongate you. This is a recent trick that I discovered, and am so glad for it.

As you see here, because the skirt falls down right above the ankle boots. the simple style of the skirt and the black ankle boots creates a leaner and longer silhouette.

And finally, this definitely applies to you, if you are a Petite or in general have a petite frame, avoid chunky ankle boots with midi skirt as they naturally draw a lot more attention and in turn will make you look short. Opting for pointed toe and heeled ankle boots will help your legs appear longer in them which will elongate your overall look. This ie one trick that I always use for all my midi skirt outfits because even though, I would not call myself Petite, but because of a shorter torso, I can look petite and small in many outfits.

How to Not Look Fat

This happens specially with Tulle skirts, or pleated skirts which are flowy that falls wider below your hips. I have another blog post where I am sharing a Tulle skirt style guide that will help you with  styling your them better, but there are just a few ways you can style any fuller midi skirt with ankle boots that will not make you look bulkier in them.

The first rule is to not wear an oversized top if you are wearing a flowy or wider skirt and it really does not matter whether it is a mini or a midi skirt, but this definitely applies to midi skirt with ankle boots that are already making you look shorter. I prefer wearing fitted sweaters or tops that are hugging my waist which creates a structured shape and will give you a leaner look. 

If you have a longer top or sweater, making sure that you tuck that in will help you create that waist definition. You can also add a belt in case you cannot tuck in the top which will also help create an hour glass look. 

Another way of creating a slimmer silhouette is by wearing narrow heeled ankle boots or fitted ankle boots that hug your ankles. This makes your ankle look leaner and creates a leaner look which naturally helps you look leaner in a flowy skirt. If you cannot find a narrow heeled ankle boots because they are uncomfortable , following this step will definitely help. 

How to Not Look Frumpy

Its really difficult to make midi skirt outfit look frumpy, unless you are picking a midi skirt that is just too heavy on prints or does not flatter you at all. But there are some more things you can do to completely avoid looking frumpy in them.

The first and foremost is to pay attention to the overall fit of the outfit. if you are wearing something oversized make sure that you add a belt or wear a midi skirt that is more structured. When I am in doubt, I always pick a pleated midi skirt, because they naturally look structured because of the pleats. You can also achieve this by wearing a structured minimalist ankle boots with a little bit of heels. This way you creating a structured style that looks pleasing. 

Pay attention to the color combination of the outfit which is just not applicable to midi skirts. If you are wearing too many colors, your while outfit might look out of the place and frumpy and weird. I have a rule of keeping my colors to a maximum of 3 colors. This way I know that I am creating a cohesive outfit. 

Even though a lot of us are seeing chunky lug style flat boots, I personally cannot wear them with midi skirts. They automatically date my outfit and do not look flattering at all. But if you want to wear lug sole chunky boots, pick the ones which have narrow toe style instead of rounded toe. And have a bit of heels, which helps elongate your silhouette and make you look chic.

Boho Chic Sweater Blazer Outfit - Pic 2

How to Dress Down Midi Skirt with Ankle Boots

All of the above style tips might make you feel like, all I am sharing are fancier ways of wearing midi skirts with ankle boots. But it does not have to be. Though I find midi skirts to be a dressed up clothing item, there are ways you can create casual yet elevated styles with them.

I love wearing leather jackets or denim jackets with midi skirt that add an edgy and a casual touch to the outfit. Even if you are wearing heeled ankle boots which might appear fancier, pairing a casual third layer will create a casual look that you can wear for everyday style. I have even done that with Tulle skirts

You can also pick ankle boots that look more casual like picking ankle boots which have hardware details will create an edgy look. On the other hand picking a neutral colored ankle boots or even tan boots will add a casual touch to your outfit. These color tones have a way of not looking as intense that  black or white ankle boots can feel like. 

You can also achieve this by wearing a casual top like just a T shirt, or a plain V neck sweater, or even a sweatshirt that will create a casual look with the midi skirt. As long as you are making sure that they are not too oversized and you are creating a structure, your outfit will be perfect for everyday wear. 

How to Dress Up Midi Skirt with Ankle Boots

It is really easy to dress up Midi skirt and ankle boots outfit, by simply picking a fancier top and outerwear. I have a blog post where I am sharing some Tulle midi skirt outfits that will help you feel inspired for the holiday season. 

But if you are looking to feel fancier in a midi skirt, then always combine a print with solid. you can wear a printed skirt and solid midi skirt with a printed sweater like a fair isle sweater which is my favorite for the holiday season. 

Or you can pick a printed skirt and pair it with a solid blouse or sweater. This way you not only have a chic outfit, it also looks cohesive and balanced. 

Below are some of my favorite midi skirts that will effortlessly elevate your outfits.

And a pair of black narrow heeled ankle boots is like an essential for every woman. You don’t have to wear super high heels. The one I am wearing is just 3 inches. You need to make sure that they are simple and have no contrasting hardware which can create an edgy look. These ankle boots look great with anything and they specially elevate my midi skirt outfits.

You can also pick skirts that are more stylish like leather midi skirts which are my favorite for cooler months. But if you are wearing leather skirts, make sure that you pick ankle boots that are minimal, so they don’t over power or look out of the place.

Styling Bias Midi Skirt

If you are wearing a bias midi skirt which is usually longer in length and makes you look straight because of the straight design of the skirt. Wearing ankle boots that are lighter in shade than the color of the skirt will make you look shorter and not so flattering. But if you pick ankle boots that match or are darker in color, it easily elongates and makes you look taller with the boas midi skirt.

Shop The Look

Styling Pleated Midi Skirt

Pleated skirts are an essential and an easy way you can wear heavier sweaters as well. I love pairing pleated skirts with cable knit or even fair isle sweaters. Because of the waistband, a pleated skirt always looks flattering on any body type. I am a big example as I have a straight figure. 

Now, if you are wearing a lighter sweaters or blouses, you can still wear white ankle boots and get away with it. This is because the waist definition is already creating a body shape and your legs do not look cut off because of the skirt.

Styling Leather Midi Skirt

Leather midi skirt looks really chic and stylish and great addition to your wardrobe for any season but specially for fall and winter because you also feel cozy in them. 

Most of the time we prefer buying black leather or faux leather skirts because they are the easiest to style. But, now there are so many pretty faux leather skirts in different colors that I cannot resist. 

When pairing ankle boots with these faux leather skirts its important to pay attention to the material of the ankle boots. If the skirt is shinier and darker tone, make sure that you are wearing suede boots or more non shiny boots. 

But if you are wearing lighter colored leather skirts, wearing a shiny boots can easily work.

Shop The Look

[Polo Collar Sweater] | [Faux Leather Midi Skirt (Sold Out) – Burgundy color Available] | [Suede Ankle Boots]

Styling Printed Midi Skirt

Printed midi skirts are not just for spring and summer. You can wear them for fall and winter. And if you can find a red or other holiday color ones, then its cherry on top. 

I am so glad that I found this one from Ann Taylor. The easiest way to style a printed skirt is by creating a monochromatic outfit matching the base color of the skirts. 

Ofcourse, if you feel that matching everything is an overkill, you can tone it down with the accessories and your ankle boots. You can wear a contrasting colored one to create a depth and personality. But sometimes its not needed because the print details of the skirt creates that texture.

I would love to know what is your favorite midi skirt and ankle boots outfit. And what are you wearing this holiday?


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About Suchi

A Techie turned Fashion blogger, I have been in your shoes. I have gone from looking like I was trying to fit into my teen clothes, to now a stylist and blogger known to be classy and elevated style. I can help you look your best without spending too much time, effort and money into your wardrobe. 

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