How to Wear a Midi Skirt – 10 Ways to Wear a Midi Skirt

October 30, 2019

I recently added this amazing snakeskin midi skirt to my collection. If you’ve been reading for any length of time, you know I LOVE midi skirts!! When working on this post, I figured I would round up some of my favorite midi skirt outfit posts and easily came up with 10 ways to wear a midi skirt. Below you will find examples of how to wear a midi skirt in spring, summer, fall, and winter. You’ll find midi skirts with sweaters, heels, sandals, and more. From sneakers to workwear looks, they are so versatile and easy to wear!

Midi Skirt Fit Guidelines

I hope this will give you some inspiration and tips. As a general rule, you want a midi skirt to hit at the narrowest part of your waist and flow out. You want it to stop mid-calf or just above. If you are shorter and haven’t tried a midi skirt, I highly recommend giving them a try. It’s possible you just have not found the right fit for you and would need to have it shortened. They are very elongating. I truly think midi skirts are universally flattering  for all body types and heights. 

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How to Wear a Midi Skirt in Fall and Winter

Below is the newest midi skirt fall outfit with this gorgeous pleated snakeskin midi skirt. Since the temperatures are starting to cool off, I added a knotted sweater and boots. Covering my feet and wearing a warm sweater made this a perfect fall/winter look. For any of these fall looks, you could easily add tights or taller boots and a heavy coat and be good to go for even cooler winter months. I’m including my leopard skirt look which I recently posted here. I styled it with sneakers and a faux leather jacket, but recently I swapped the sneakers for over the knee boots and the leather jacket for a belted blazer (also pictured). It was a much more winter like day, so these swaps were perfect for the weather with a coat over my outfit.

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Shop the Above Outfits

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How to Wear a Midi Skirt in Summer

As for a summer midi skirt outfit, I love wearing a tank top and sandals. One example below is a much more casual look with a tied cotton tank and fun accessories to complete the ruffled leopard midi skirt. Another is an all blush look that is totally a work appropriate outfit. Heeled sandals and a dressier, ruffled top make all the difference. Consider adding at belt at the waist for more definition and an even dressier look. I also included a matching set example with lighter colors and a short sleeve shirt appropriate for spring or summer and many occasions. 

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How to Wear a Midi Skirt in Spring

For spring, I love wearing a longer sleeve blouse. Depending on the weather, you can either do a closed toe or open toe shoe. 

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A Note on Midi Skirt Material for Seasonal Wear

When considering what midi skirt to wear when, it can be very helpful to think about material and print. For example, a sweater weight midi skirt can be perfect for winter! Or velvet or pleated burgundy midi skirt. Even a leather midi skirt can be fun for fall, winter, or spring. Pair any of these with boots and a sweater for an ideal winter midi skirt outfit. For summer, think of a gingham or brighter colors. 

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  • Reply Cheryl Shops November 3, 2019 at 10:39 pm

    Midi skirts are the most flattering, especially when you get to be my age 😉 They all look great on you!
    Cheryl Shops |

  • Reply Jessica November 3, 2019 at 2:12 am

    These are all so pretty dear, especially the striped dress. Love the pop of the red heels too.

    Jessica |

  • Reply Emma Peach November 2, 2019 at 2:30 pm

    Such fabulous looks! I love the snake and leopard print skirts!

    Emma xxx

  • Reply Merritt Beck October 30, 2019 at 5:13 pm

    I love to wear a midi skirt all year round! This is great inspo!

    xx, Merritt

  • Reply jess jannenga October 30, 2019 at 1:28 pm

    Hi Amy! I adore this midi skirt on you! The neutral pallete is gorgeous! I love with the black booties and how you tied the top. i have a midi snakeskin skirt I bought probably about 4 years ago before the trend and I love it.
    jess xx

  • Reply Lizzie October 30, 2019 at 10:56 am

    Ahh I want all of these outfits! You have the cutest sweater and skirt collection!


  • Reply Rachael Thomas October 30, 2019 at 10:23 am

    You have the best collection of midi skirts! I love these styling tips and how you make them perfect for everyday wear!

  • Reply Ashley October 30, 2019 at 9:48 am

    Your midi skirt tips are ace- I really love a midi with a sweater and boots for fall and winter! That snakeskin number is so gorg!

    Le Stylo Rouge

  • Reply Shelbee on the Edge October 30, 2019 at 9:08 am

    Oh wow, Amy Ann! So many great styling ideas for flirty feminine midi skirts! I feel like I have a million new things I can do in my closet now!


  • Reply Kelly R October 30, 2019 at 8:40 am

    Midi skirts are SO cute and I love how you styled yours! Perfect transitional looks!

    Rosy Outlook

  • Reply Kate October 30, 2019 at 8:28 am

    So many beautiful looks, loving all the gorgeous colors and pleats <3

    Green Fashionista

  • Reply Rosemary Davis October 30, 2019 at 8:26 am

    A gorgeous skirt! I love each and every way that you have styled it!


  • Reply Ellibelle October 30, 2019 at 8:22 am

    These all look fantastic on you! Such beautiful classic outfits!
    Ellibelle’s Corner

  • Reply Heather Noire October 30, 2019 at 6:31 am

    It’s such a versatile skirt. I love how you can wear it all season long, and with so many unique looks 🙂

  • Reply Meagan Brandon October 30, 2019 at 6:27 am

    I’m posting a roundup of midi skirts on my blog this Friday – how funny! And I’m posting the same snakeskin skirt! Isn’t it great? I’ve worn it a bunch this fall. Love your outfit inspo!


  • Reply Julie | This Main Line Life October 30, 2019 at 5:50 am

    These are all beautiful midi skirts. I especially love that snake print skirt and the pink one with the black details.

  • Reply The Fashion Folks October 30, 2019 at 5:03 am

    I love midi skirts and I agree that they’re great for fall too. So cozy and fashionable to pair them with a sweater! Xx

  • Reply Radi October 30, 2019 at 2:46 am

    I love the summer looks. They make me wish it was summer all over again.

  • Reply Jill October 29, 2019 at 5:36 am

    I’ve been wearing midi skirts more often and love all of this inspiration! All of these outfits are gorgeous!

    Jill – Doused in Pink

  • Reply Elisa October 29, 2019 at 3:52 am

    I love midi skirts and all the outfits you shared are fab!
    xx Elisa | DIY & LIFESTYLE BLOG

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