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How to Find the Perfect Midi Skirt

If you’ve ever pulled a midi skirt off the rack and wondered why it’s not exactly looking right, I get it. This style and cut of skirt can be a little challenging to wear, especially if you don’t have a completely flat tummy or the longest legs, but I promise: when you style it correctly, you will LOVE midi skirts! Whether you accessorize with strappy sandals, booties, sneakers or taller boots, I’ve got you covered with all the tips and tricks on how to find the perfect midi skirt!


What is a “Midi” Skirt or Dress?

Simply put: a “midi” skirt or dress is the length that falls between your knees and ankles, or in the “midi” area of your legs. It’s not a mini (above the knee) or a maxi (floor length), but a midi (mid-length)!

How to Style a Midi Skirt

1. Accentuate your waistline:

The No. 1 rule to remember when wearing a midi skirt, no matter your size, is to accentuate your waistline. This simple tip can make or break your midi look. Truly. By wearing a belt and/or tucking in your shirt, you’re creating {sometimes an illusion} of an hourglass shape. This trick does wonders even if you don’t have an hourglass shape at all!

This pleated skirt naturally cinches in my waistline, helping create that hourglass figure. The puffed sleeves also help create the illusion by making my shoulders wider.

2. Tuck in your shirt:

A tucked in shirt is sure to give you that waistline to make the silhouette of a midi skirt POP! If you don’t tuck in your top, you’ll end up with a messy (and bunchy) silhouette. Ideally you want your top to be form-fitting, with the bottom of your top (or cardigan) hitting right below the waist line of the skirt.

Want to make it super easy? Pair your midi with a body suit. Y’all know my love for bodysuits, and this option works SO well, especially paired with a skirt. And don’t be fooled: all bodysuits don’t have to be form-fitting if you’re worried about that. You can totally get a bodysuit that has some draping, which helps draw the eye away from the midsection, which I wore here with a snake print mini skirt.

If you’re going for a chunky sweater winter look, for example, still utilize the front tuck. A front tuck is where you simply tuck the very front part of your top or sweater into your waist band and pull a bit of it out to create draping.


Midi Skirt Styled with Jean Jacket
I have a top tucked into this midi skirt and chose to wear a cropped jean jacket that hits right below my hips.

3. Find the right length:

No doubt this is where most women get hung up on pulling off the midi length trend. The ideal length for your midi skirt or dress is either above or below the middle of your calf. The goal is to not have the skirt or dress hit exactly in the middle of your calf, which is the thickest part of your leg.

I’m on the taller side (5’7″), so most of my midi skirts and dresses hit above the mid part of my calf. If you’re on the more petite / shorter side, a general sized midi will probably hit below the middle part of your calf. Either length can work, depending on footwear choice. But if you are 5’4″ or shorter or if you have shorter legs overall, definitely opt for petite sizing and aim for the length on the upper part of your calf.

Ashley T, Charleston Blogger, at White Point Gardens downtown Charleston
This midi sun dress hits below my knee but above the thickest part of my calf, so I could easily wear sneakers or sandals with it!

3. Mix up your footwear:

Generally speaking, a footwear option that looks great on everyone wearing midi length are heels. Heels will elongate your legs, helping give your skirt lots of movement. In my pink pleated midi skirt outfit, I wore strappy block heels, which really dressed up my whole look but made my legs look long.

If you’re wearing a fall or winter midi skirt, heeled booties and heeled knee high boots are also great options to maintain some warmth to your outfit. No matter your body type or height, heeled versions are great!!

Here’s where it can get a little tricky: to avoid looking like you’re drowning in your skirt or like your legs are cut where the skirt ends, only wear flat shoes with a midi skirt if:
1. You’re tall (any length of skirt with any shoe type will work for you)
2. Your skirt hits the upper part of your calf, right under your knee.

If you fall into one of those two categories, wear all the flats you want: sneakers, loafers, mules, flat boots, flat sandals. So many cute and comfy options that look GREAT with the midi length.

How to style a midi dress
This midi dress hits below the thickest part of my calf, so I would only wear heels with it to avoid my legs looking cut off and “stumpy.”


My Favorite Midi Skirts for Fall / Winter 2020:


  1. Pleated skirt: There is something so beautiful and classic about a pleated midi skirt. It’s perfect dressed up with heels and a fancier top or even dressed down with sneakers and a sweater.
  2. A-line skirt:


My Favorite Midi Dresses for Fall / Winter 2020:

If you’re loving the midi length and want to venture out to midi dresses, I’ve rounded up some of my favorites:

1. Women’s Sleeveless Tiered Ruffle Dress

A dress perfect for everyday wear! You can wear this dress with some cute sneakers or espadrilles and wear it to lunch or a day date!

2. Women’s Short Puff Sleeve Tiered Babydoll Dress

If you’re planning on going to a wedding shower, baby shower or a luncheon, this dress is perfect for you! It’s a little bit dressier, but not too dressy to wear during the day. It’s midi length would go great with a pair of sandals or pumps!

3. Women’s Slip Midi Dress

Date night is calling! This dress is perfect to wear out on a date with a cute leather jacket, your favorite crossbody and some strappy sandals, and it’s burgundy color is perfect for the season!

4. Women’s Flutter Short Sleeve Dress

Another dress perfect for everyday wear! You can throw this dress on and hit the town! The good thing is, it’s flowy and breathable for those of you that have warmer fall and winter months.

5. ASOS Design High Neck Pleated Midi Dress

I couldn’t finish this list without a formal option! If you’re looking for the perfect midi dress to wear to an upcoming wedding, look no further! The color and design of this dress is sure to turn a few heads!




midi-dress-skirt-trend dress-skirt-style-trend

How I Styled the Trend

I opted for a pleated, flowy skirt with a cute puff sleeve blouse and my favorite pair of black, strappy sandals. There are so many different ways you can wear this trend, but if you’re looking for something simple, I highly recommend looking through Pinterest for some ideas! Don’t be scared to try out a new trend, you’d be surprised how creative you can get!

Shop the Trend

As always, if you missed my last post, check it out here! I’ve also posted a few gift guides that you can find on the homepage of my blog!
Ashley T
Ashley T

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