Midi length dresses and skirts, both flared and form fitting, are trending now and for the next couple of seasons. It’s important to get the footwear right in order to wear them with panache and avoid looking and feeling dowdy. Petites, don’t despair because you can wear midis. Refer back to my shopping trip with gorgeous Laura, where we successfully fitted midis on her petite self by looking for the right shape and length. 

Pictures speak louder than words so below are visuals of midi dresses and skirts to accompany each footwear option.

  1. Heeled Platform Loafers: The lower the colour contrast between your legs or hosiery and the loafers, the longer the leg line. This is a trendy pairing.
  2. Knee-High Boots: The model is wearing low heeled boots with this frock and it’s worth watching the video to see the dress and boots in action. Tall high heeled, wedged, and platform boots will also work. By all means wear flat riding boots with a midi that defines your waist if you already have a relatively long leg line.
  3. T-Strap Mary Jane Pumps: Super retro and of course, the socks are optional. They don’t need to be four inches high (2.5 to 3 inch heels are just as fab).

  1. Flat Hiking Boots: This more grungy take on the midi ensemble is hard to pull off, but fun with a little youth or spunk on your side. Tucking into a waisted midi will lengthen your silhouette. You might find the proportions more flattering with a form fitting midi and/or with “haute hiking boots” that have a substantial high heel.
  2. Heeled Sandals: The photo shows platform sandals, but most heeled sandals, cage heeled sandals, or heeled sandal wedges will work. Heeled peep-toe sandal booties are a more fashion forward choice.
  3. Pumps: This is the easiest footwear option to pair with midis. Pumps can be low heeled (kitten), high heeled, stiletto, stacked, wedged or platform. I wore three inch stacked heel pumps with my form fitting midi dress and flared midi skirt.

  1. Ankle boots or booties: These work particularly well in low heeled styles when the colour is low contrast against your skin or hosiery. The snug fit around the ankle creates a more streamlined effect. Form fitting booties, like I recently wore with my harem pants, are another great choice.
  2. Platform Booties and Monster Wedges: Note how streamlined the booties fit around the ankle, which I think is key. Also, the bookended black bootie and outfit work particularly well.
  3. Calf Length Boots: I’d be weary of this combination unless you have a naturally long leg line. Here, it’s important to define the natural waist, thereby lengthening your legs and minimizing that “stumpy” feeling.

Most of the photos show high heeled footwear, but that’s not your only option. I cannot walk in three inch heels all day so I wear low heeled pumps, booties, ankle boots, and knee-high boots with my midis. I also fully intend to wear casual flat riding boots with midis, but haven’t done so yet. Ballet flats will also work if you keep the midi on the shorter side with a very defined waist. Again, look at how our petite and curvy Captain Dress sports the look.

Feel free to ask further questions in the comments section and I’ll answer them as best I can.

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