How To Wear A Midi Dress ft. 11 Cool Girl Outfits & Shoe Tips

A lot of glossy magazines write that midi dresses are “mature.”

If you’re anything like me, when you see something described as “mature,” you run.

How to wear a midi dress casually

Midi dresses are more reserved than a short sundress, but that doesn’t mean they’re any less youthful. Midis offer a certain subtlety that a mini sundress can’t. That means we can have a bit more fun styling and wearing it.

Let’s investigate how to wear a midi dress casually, because, you know, we’re young and don’t have to be dressy & whatever.

How To Style A Midi Dress Casually

A midi dress hits your legs mid-shin (right between your ankle and knee). This means that for a midi to flatter you, you really need to pick the right shoe.

But before we get into types of shoes to wear with a midi dress, one key thing to keep in mind is your handbag…

Bags & Midi Dresses

If you’re going to wear an across body bag with a midi dress, you will want your bag to drop right where your hips are.


This is to keep the proportions of your outfit in line with the length of the dress.

If your bag is lower than your hips, you’re going to look longer, but not in a good way, see what I mean above?

Now, back to outfits!

In all of these outfits I’m wearing Réalisation Par’s Juliet dress. It’s an ideal midi because it has a youthful feel with its ruffled trims, but still looks put together.

Here are 11 casual midi dress outfit ideas, along the shoes to wear it with.

What Shoes To Wear With A Midi Dress

Midi Dress with Sandals

Slides: The easiest sandal just made the easiest dress even easier.
Strappy Sandals: A strappy sandal that doesn’t tie at the ankle won’t cut off your legs, so they’re great for midi dresses.
Gladiator: If you have longer legs, these are ideal. I’m 5’5.75, so right in between short and tall, and they still work.

Midi dress with sandals outfits

Left to Right: K. Jacques mules with a Smythson Wallet, and Celine sunglasses; K. Jacques sandals with tote bag, necklace, and Dita Sunglasses; K. Jacques Epicure sandals with a vintage bag, and Ray-Ban Clubmasters.

Midi Dress with Flats

Slides might be the easiest sandal to wear with a midi dress, but the ballet flat is the easiest shoe. They require no effort whatsoever.

If you want to add a little height, you can grab a pair that have a little heel, like Repetto Camille flats.

Midi dress with ballet flats outfits

Left to Right: Repetto flats with Celine sunglasses, and a vintage bag; Chanel ballet flats, Jennifer Fisher x Goop earrings, and a Marc Jacobs clutch; Repetto Camille flats with Jennifer Fisher x Goop earrings, and a vintage bag.

Midi Dress with Trainers

Converse: Given the choice, I will always vote for high top Converse. Despite their notoriety for making legs look shorter, they work well with midi dresses. You just have to counter it with a bag that plays well with the proportions.
Stan Smiths: A white sneaker never hurt an outfit…

How to wear a midi dress with trainers

Left to Right: Converse with Celine sunglasses, Jennifer Fisher x Goop hoops, and a tote bag; Adidas Stan Smiths with Jennifer Fisher x Goop hoops, and a tote bag.

Midi Dress with Espadrilles

Espadrilles are the summer shoe of French It Girls like Jeanne Damas.

A wedge espadrille, like these from Castañer (review here), gives you an extra 2.5” of height. Not only that but the way they lace up your leg adds some subtle seduction to your outfit.

Midi dress with espadrilles outfits

Left to Right: Castañer espadrilles with David Yurman hoops, and a Chanel bag; Castañer espadrilles with a chain, Celine sunglasses, and a Kayu tote; Castañer espadrilles with Jennifer Fisher x Goop earrings and a Marc Jacobs clutch.

Have fun with your midi dress outfit…

Despite what “they” say, midi dresses are for the stylish and young!

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