What Shoes To Wear With A Midi Skirt
Photo Credit:Mariana Ramalho
You finally found the perfect midi skirt. It fits, it flows, the length is just right… and now it’s just sitting in your closet because you have no idea what shoes to wear with it.
You’re not alone.
Shoes can make or break a midi skirt outfit. Too chunky, and it feels off. Too dainty, and it feels too dressed up. Heels can feel like overkill. Sandals sometimes look like you gave up. And let’s not even talk about boots—those are a whole other mind game.
If you’ve ever stood there second-guessing the whole outfit just because the shoes didn’t feel right, this post is for you.
I’ve broken it down by real-life moods and situations—so you can stop Googling “what shoes go with midi skirts” and actually wear the skirt you love. These are the shoes that just work. No fashion degree required.
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Need help styling the rest of your outfit too? Grab my free 365 Outfit Ideas—so you’re never stuck staring at your closet wondering what works.
1. For Casual Days When You Still Want to Look Cute
These add a soft, polished touch without trying too hard. Think errands, coffee, bookstore run.
Woven Ballet Flat
$69.99
2. For Brunch or Lunch Dates When You Want a Low Heel
They elongate your leg without the pain of a full heel. Especially good with satin or flowy skirts.
Kitten Heels with Bow Pointed Close Toe
$56.99
3. For When You’re Running Around All Day
Clean, minimal sneakers keep it comfy without making the skirt feel too dressed down. Just avoid anything too bulky.
New Balance Women's 515 V3 Sneaker
$74.96
4. For Work or Anywhere You Want to Feel Polished
These bring structure and style—perfect with pleated or structured midi skirts.
Casual Loafer Flats Slip On
$39.99
5. For Summer Nights or Outdoor Events
If the skirt already makes a statement, go for simple sandals that show some skin and keep things light.
Cross Strap Sandals
$38.99
6. For Fall or Transitional Weather
Try: Sock boots or fitted ankle boots with a block heel
Make sure they’re slim at the ankle so they don’t fight with the shape of the skirt. Great with thicker fabrics like ribbed knit or denim.
Minimalist Pointed Toe Chunky Heeled Ankle Boot
$59.99
7. For Chill, “Not Trying Too Hard” Outfits
They give a relaxed energy while still balancing out the length of a midi. Especially cute with a tucked tee or tank.
Chunky Wedge Lug Sole Open Toe
$59.99
8. For the "I Want to Wear This to Dinner" Look
Instantly elevates the outfit. Keep the heel low or mid if you still want comfort—don’t overdo it.
Slingback Heel
$49.99
Need help styling the rest of your outfit too? Grab my free 365 Outfit Ideas—so you’re never stuck staring at your closet wondering what works.
