10 Shoes to Wear With Midi Dress

Midi dresses are a favorite of mine for easy and chic styling! However, sometimes it can be hard to know what shoes to style them with. Midi dresses are so flattering and versatile, making them perfect for many occasions. One of the best things about midi dresses is how pairing them with different shoe styles can completely change the look. From casual to elegant, the right shoes can elevate your outfit effortlessly. So today, I’m excited to share a guide on what shoes to wear with midi dresses. I’ll be showing you 10 different shoe styles that pair perfectly with midi dresses, helping you find the right look for any event! Whether you’re dressing up for a formal occasion or keeping it casual for a day out, these shoes will help you feel confident and stylish in your midi dress.

Also, if you’re looking for more shoes to style with your dresses this summer be sure to check out my post on 6 Shoes to Wear With Summer Dresses.

10 Shoes to Wear With Midi Dress

What Shoes to Wear With Midi Dress

Sharing a variety of chic shoes to style with your midi dress year round.

Ankle Boots

Ankle boots are a great option to wear with midi dresses because they add a stylish edge to your outfit. I especially like wearing them in the fall and winter to keep warm. They’re perfect for more casual chic occasions. For workwear, pair ankle boots with a satin midi dress and a blazer. For a casual day out, wear them with a knit midi dress and a jean jacket. This versatile style makes ankle boots a go to choice for many different looks. I also love styling ankle boots with jeans. Check out my post on How to Wear Ankle Boots With Jeans for more ideas for how to wear this look!

White Sneakers

White sneakers are perfect for a relaxed midi dress outfit because they’re so timeless and comfortable. Style them for anything from running errands, to casual lunches, picking up the kids from school, and more. I love wearing them with a cotton or linen midi dress for an easy, on trend look. Of course, don’t forget to check out my post on the best white sneakers to wear with dresses for more style ideas.

Block Heels

Block heels are another great option to style with a midi dress outfit. They come in all different styles, like pumps, sandals, and more. Also they are usually more comfortable than stilettos. Block heels are great for elevating a casual chic look, where you want to feel both stylish and comfortable. Whether you’re going for a relaxed day out or a polished work look, block heels are a great way to elevate your midi dress look.

Heel Sandals

Heel sandals are a favorite of mine in the spring and summer. They will instantly make your midi dress outfit look refined for when you want to dress up but still feel comfortable. I like pairing heel sandals with a flowy midi dress for a garden party or dinner date. Opt for a chic silk or linen dress to keep the look comfortable and stylish!

Combat / chelsea Boots

Combat boots or chelsea boots are perfect for adding a cool vibe to your midi dress outfit. They’re perfect for casual outings like a concert or outdoor occasion, especially in the fall and winter. These boots add an edge to your look. Because of this, I love styling them with a knit or wool dress. They bring a comfortable and on trend look to any outfit.

Knee High Boots

Knee high boots are great for pairing with a midi dress outfit in the fall and winter. They’re great for cooler weather. They also tend go well with thicker fabrics, making them perfect shoes to wear with a knit midi dress for a workwear or special occasion. Whether you’re heading to the office or a chic holiday party, these will have you looking timeless. Also, be sure to check out my post on what shoes to wear with sweater dresses for more ideas.


Loafers are a comfy and sophisticated option for pairing with a midi dress. They’re perfect for work or meetings at the office. Opt for a tailored midi dress with a blazer to complete your look. Overall, loafers are ideal shoes to wear with a midi dress for a polished and chic outfit idea.

Ballet Flats

Ballet flats are a timeless and classy choice for a midi dress outfit. They’re also a favorite of mine. Perfect for casual and semi formal occasions. I wear ballet flats with a flowy midi dress for an elegant look. Or also even with a light linen dress in the summer for a more casual chic look. They’re a great option if you want to look classy and put together.

Kitten Heels

Kitten heels add sophistication to a midi dress outfit without sacrificing comfort. They’re great for work, dinner parties, or date night. I personally love to pair kitten heels with a silk midi dress and a leather jacket for an on trend date night look. But the options are endless with this chic combination.

Flat Sandals

Flat sandals are my go to for a relaxed midi dress outfit. They’re great for summer days and casual outings. I especially love to pair flat sandals with a cotton or linen midi dress for an easy look. They go well with light fabrics for the summer and springtime. Whether you’re by the beach or strolling in the park, flat sandals are a comfortable and chic option.

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Shoes to Wear With Midi Dress

Check out my latest posts for more chic inspiration!

Please feel free to email me at thegraydetails@gmail.com if you have any questions!  I’m always happy to help with styling or picking out a specific outfit for an event!   Have an amazing day!!

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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