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Dearest reader, a midi dress is one of your closet or capsule must-haves. It is one of the most forgiving and flattering styles of clothing. It works well on most body types, and the same can be said for shoes. Depending on the style, a midi dress can be paired with almost any type of shoe throughout the year, including sneakers, espadrilles, flats, heels, and boots.
The only caveat I offer is that I wouldn’t pair a midi dress with boots in the UGG style. Sure, it’s comfy, but it also makes the calf look chunky when paired with a midi dress.
FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point.
But What is a Midi Dress?
For this article, a midi dress has a hemline that usually sits mid-calf or slightly higher but below the knee. It can be a wrap, tiered, a-line, fitted, fit-and-flare, ruffled, or with a nice slit or two dress, and this dress type is suitable throughout the year, depending on the fabric and fit.
Stick with me as we head over to the shoe closet to find a shoe that works well with your midi dress.
Sneakers
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The midi dress with sneakers, usually low cut white or light-colored in neutral tones, paired with a floaty midi dress and some silver or gold accessories, is a staple across the ages. It offers a carefree, last days of summer look for younger women, and for older women, the style is flattering and the sneakers comfortable. It is a versatile look for holidaying and a fuss-free option for mothers on the school run who need to meet their pals for an early coffee and croissant.
Dark sneakers don’t work as well with midi dresses, and this might have to do with the fact that a lighter shoe elongates the leg and doesn’t detract from the dress itself. But as always, there is an exception to every rule, but this depends wholly on the dress. A white or light dress may work well with an indigo denim sneaker.
Your type's signature aesthetic, color palette, and capsule wardrobe — in one guide.
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Do not, I repeat, do not pair your midi dress with hi-top sneakers. It’s almost impossible to do unless you are Zendaya, so if you can, avoid this pairing.
Sneakers and midi dresses are spring, summer, and early fall staples.
Espadrilles and Wedges
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Espadrilles and tiered midi dresses are a match made in heaven. Espadrilles lend you a little height, which is helpful if you are shorter in stature and they will elongate your legs. Where an espadrille is working, a wedge will work too.
A wedge gives you even more height but the comfort that a traditional heel cannot. Pairing espadrilles with a wrap or tiered midi dress gives you a smart casual vibe suitable for afternoon weddings, summer lunches, and twilight barbeques. Pair this look with a denim jacket, and you are good to go.
Espadrilles and a midi dress are spring and summer’s purview, particularly if your dress has a pretty floral pattern.
Flats
If you can’t bear the thought of sneakers or espadrilles, especially if you live in or near a beach town, then slide-in flats should be your first choice. The good news is that we are currently seeing a trend towards highly detailed flats with chunky gold detailing or heavily accented flats with pseudo pearl clusters. Sandals with a bit of lacing around the ankle or diamante detailing on the front are also suitable with midi dresses and will flatter a plainer midi dress in solid colors.
Your type's signature aesthetic, color palette, and capsule wardrobe — in one guide.
Flip flops work for an excessively casual look, and midi dresses with a kaftan style. Your rule of thumb should be that if it is appropriate to go barefoot in your midi dress, you can wear flip-flops. Here’s looking at you, Byron Bay.
Closed flats are trickier to match with a midi dress and may require a bit of trial and error, mainly because they tend to be dark-colored and done incorrectly will add age and frump. Ballet flats are your safest bet here and work best with an a-line midi dress.
Heels
Heels are a category all on their own.
Closed or sling-back heels work best with a fitted or, better yet, a fit and flare midi dress, and this pairing is an office staple. Depending on the color of your dress, nude and tan shoes are the most versatile. Think courtroom/lawyer TV dramas, and you’ll immediately know what I mean. This look can be paired with sheer stockings in winter but bare-legged with a touch of sun, real or fake works in summer. Finish it off with a trenchcoat during the colder seasons, and you are on-trend this year.
For summer, strappy heels work well for functions, and block heels are practical and are suitable in a formal and casual setting. They offer the benefit of not sinking into the grass if your milieu for the day is a garden or winery with rolling lawns.
In general, heels of most heights and styles work with midi dresses. A kitten heel slide, in particular, is a nice look for a summer wedding.
This look is suitable year-round.
Boots
Different types of boots work well in different ways.
Ankle boots with a heel are suitable in the same way a court or dress heel is ideal with a more fitted or fit and flare midi dress. On the other hand, flat or chunky heeled mid-calf to knee-high boots work well with a-line midi dresses providing a pleasant texture contrast.
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Finally, if you want a manic pixie fairy look, combine combat boots with a midi dress featuring a tulle skirt. Think 90s Doc Martens revival.
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Boots and midi dresses are suitable for autumn and winter looks, paired with a coat and a lovely scarf of either wool or silk.
Put your best foot forward, wearing your favorite midi dress and shoe combo. It is tough to get this styling wrong, and as I said, a midi dress is flattering for most body types, heights, and age categories and the best part is that it pairs well with almost any type of shoe. Search the web, online retailers, and, more importantly, this blog for online inspo!
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