Post updated with new shoe favorites on March 13, 2024
"I don't want to look frumpy". I hear it alllll the time in the dressing room when I present a "midi" length dress or skirt to my clients. A midi falls somewhere around calf length on women of average height. Let me just say I never want you to look frumpy either.
This dress is fabulous, not homely. That v-neck... The ties that cinch your mid-section and yet conceal your tummy... The tiered fabric that lets you wear white without Spanx... The fact that I don't have to tan or shave my legs before going out... so, so good... LOVE!
Let's use this dress as our styling example while I answer the question "But what shoes do I wear with a midi dress?" Keep scrolling to see seven different shoes that I paired... and you can wear... with this dress... or any midi dress of your choosing...
Shop The Dress...
Lucia Tiered Cotton Blend Midi Dress
RAILS
Shop now ›
Lucia Tiered Cotton Blend Midi Dress
RAILS
Shop now ›
midi dress with a slide
Yes, wear the flat slide sandal with the midi BUT keep at least half of the top of your foot un-covered if you do. Skip the loafer, for instance, unless you have long legs. I've grown kind of attached to this black raffia sandal since ordering it last month.
Shop the Shoes...
midi dress with a heeled slide
Yes, the heel makes quite a difference. More height slims the leg. The shoe can come up a little higher on the foot, but do still show some skin. Going nude with your sandal lengthens the leg too. This sandal was everywhere last summer and it's back this year too. The square toe is on trend and the braided straps are comfortable. I'm glad it gets another spin because it goes with everything.
Shop the Shoes...
midi dress with a clear or vinyl sandal
Another shoe that matches everything is one that almost disappears. Enter the vinyl shoe that became so popular last year. It's back again! Sadly, though, this exact pair is almost sold out everywhere, but I am sharing similar styles for your consideration.
The clear straps here keep the leg from being "cut off" at all and no need to concern yourself with color-coordinating when the shoe has no color at all. I wore the HECK out of this one last summer.
P.S. to keep the vinyl from rubbing your foot and blistering, put a THIN layer of clear deodorant or a chafing stick between the strap and your skin. When I heard complaints of blisters from someone, I prepared ahead and had no problems.
Shop the Shoes...
midi dress with an ankle boot
This one is tricky, for the advanced student. I suggest a pointed toe for more visual "length". The shaft of the shoe should hug your leg pretty close and should also come up a bit over the ankle but not too far. You're going to need a little heel too. There should be a few inches of skin between the top of the shoe and the hem of the dress.
Do as you wish, but if you don't follow this advice your legs may look short and stumpy. That's where the frumpy comes in.
Are you scared? Don't be. If you aren't sure, take the bootie off. Otherwise you won't feel confident. Wear one of the other 6 styles I'm sharing.
Shop the Shoes...
midi dress with an ankle strap sandal
I gave this one it's own category because there's one "rule" to follow here...but if you don't...Hello, Mrs. Frump. The ankle strap needs to be thin, quite thin or your leg just gets cut off, and you look shorter. The key is keeping that little bit of leg you can see looking slim and as long as possible. Got that? Thin ankle straps.
Shop the Shoes...
midi dress with sneakers
Alright, here's another one that can be tricky and really just isn't for everyone. Give your dress a sporty makeover when you add a sneaker. I do this all the time but mostly for comfort when I'm on the run. Keep the sneaker a low-cut, low profile style to show a little ankle. Skip the gym sneakers, running shoes and bulky platforms with this style dress. Try a trendy metallic to take it up a notch!
Shop the Shoes...
midi dress with cowboy boots
You don't see too many people walking around everyday in dresses and cowboy boots, even here in the countryside where I live... which is why I love it. It's been a street style staple for at least a year. Personally, I'll always wear western boots with my shorts and dresses, until I just can't pull them off anymore. These boots are old favorites of mine, but I found some similar that I'd recommend to anyone looking to try this look.
Shop the Shoes...