Styling Midi Skirts

A while back I asked what sort of posts people would like to see, and “how I style X ” posts seemed like a popular option. And thus you have: How I style midi skirts! I picked this item since it seems like many people were interested in them after seeing them in some of my outfits and learning that I was 5’1″.

Psssst…what’s a midi skirt?

I actually didn’t know the term “midi skirt” until sometime in college. (Being part of cliques growing up that aggressively ~didn’t care about fashion~ will do that you ya.) In case you’re in the same boat, a midi skirt is simply a skirt that hits somewhere along the calf.

Man Repeller has a great article about the genesis and ebbs and flows of the midi skirt here which I highly recommend reading, as it’s a good overview of the history of hemlines in the 20th century, including That One Time in the 1970s When They Tried To Make Midi Skirts Happen, but they totally didn’t, because the populace wanted their modern and freeing minis!

Mini-skirted women protest the midi in Miami in 1970 (Jim Kerlin)

Although the midi-length peeked its head out via the classic 90s slip dress, it didn’t really find its footing again until the Spring and Fall 2014 collections when designers started mashing together influences from all the latter decades of the 20th century and — this is the clincher!!! — people actually liked it.

Which is kind of the point, right? If the midi debacle of 1970 achieved anything, it proved that even the most influential voices can’t sway the public if they don’t want to be swayed.

Good news: trends and progress and freedom lie in the hands of the collective.

Nowadays, there seems to be a pretty healthy selection of both minis and midis (although anecdotally, fewer maxis than in the mid 2000s – early 2010s), which is nice, so you can have some choices in both.

Screen Shot 2018-11-26 at 5.57.50 PM
Anecdata from ASOS, an online-only marketplace for a zillion brands, mostly trendier items

Half this post is disclaimers

On prescriptive style advice

I talk a lot in this post about what “looks nicer”. It felt like a ridiculous amount of stuff as I listed everything out! But don’t think of it as laws not to break for fear of The Fashion Police hauling you away, but more like concepts you can keep in mind when deciding what aesthetic you want your outfit to have. Maybe you’re going for a sturdy, stocky look. You can invert the suggestions! Also this isn’t, like, a literal checklist I go through every morning when I get dressed, but rather an enumeration of everything I could think of that I’ve internalized after scrutinizing daily outfit photos for two years.

This is the obligatory disclaimer that there’s nothing wrong about having short legs, wide ankles, skinny calves, wide calves, or any other variation in shape of the human body in that vein. However, in practice, many people including myself have been conditioned to consider a particular type of figure as ideal (namely, hourglass with legs on the longer side). I’m not going to get into the whole can of worms in this post.

And for sure, none of this is information groundbreaking, but I figure it doesn’t hurt to put a few more “how I style” examples from another perspective and on another body out in the world. I’m 5’1” and usually a US size 8 (29”/39”).

On trends

While I’ve tried to figure out from first principles why I like certain stylings better on myself, I’m definitely still influenced by current trends. I wouldn’t even be wearing midi skirts at all back in 2013 when there was rarely a midi skirt to be found in the trendy shops, and I distinctly remember when the shafts on trendy ankle booties started getting higher a few years ago I thought it was the ugliest, dumbest thing ever – “ankle boots should hit at the ankle bone, duh”.

For real, though, take a look at any of the WAYWT threads from the 2013 era on r/femalefashionadvice – it’s a different look! Except for the great therosenrot, who has her own very distinct, very awesome style.

Styling Notes

I’m going to focus on shoe choices, since I feel like length comes down to more of a personal preference (also because the demonstration photos I was planning where I would roll down the waist of a thinner jersey midi skirt to demonstrate different lengths didn’t work because it changed the way the skirt draped too much to make length the only variable).

But generally, I feel like midis that hit either slightly above or below the widest part of calf are most flattering, since they’re not highlighting the thickest part of your calf without also showing the full curve (stocky cutoff vs showing defined muscle). Though skirts that hit at that part of the calf can look better if they’re a more flared shape, since the volume of the skirt itself makes a bigger visual impact.

Note that many of the photos I reference as a less flattering option I don’t think look anywhere near awful, just relatively less flattering than the other options.

(I recommend viewing the higher res image below in a new tab)

(Left to right)
6″ shaft, 3″ heel
5″ shaft, 2.5″ heel
Oxfords with 3″ heel
Flat oxfords
Flats (I think a traditional plain pointed toe flat or d’orsay flat would have demonstrated the points better, but I only own strappy flats)
Boots with 6″ shaft and 2″ heel vs flats, but with a shorter skirt (borderline knee length / midi). I think this bodycon-like cut was called a “wiggle dress” and as you can see this stance is a tad too wide for it, as you can see some pulling across the skirt.

Observation 1: The more parts you divide your bottom half into (and/or more evenly the parts are divided), the shorter they will collectively look.


  • For a maximally leg-lengthening look, choose sandals or nude colored shoes with a bare leg or wear tights/leggings that match your shoe. If you’re digging a sturdier look (or it’s cold), wearing knee or over the knee boots that are higher than the hem of the skirt works too.
  • Otherwise, for longer midis, a boot that has a higher shaft that hits closer to the skirt hem (as opposed to a shoe that hits at the ankle bone) will be a more lengthening look because the effect is more like two pieces (skirt + boot) rather than three (skirt + leg + boot).
  • A shoe with a low vamp (the part of the shoe that covers the instep) will be more lengthening because the line of your leg gets cut off further down.


  • Longer leg effect doesn’t necessarily mean the best styling, depending on what you’re going for. For example, I like both 1 and 2 in the 5-photo collage, but while 1 gives a longer visual block for the legs/feet, 2 gives the whole look some breathing space. I’ll usually wear the boots in 1 if I’m going for a more buttoned-up Victorian sorta vibe.
    • Heck, I wear all of the combos in that collage. Just depends on what look I’m going for (or if I’m going to be doing more walking that day).
  • The thing to observe is what shoe when paired with the skirt results in the most unbroken area. In the photo with the floral dress, the 6″ shaft boots divide the legs/feet area exactly in half, which is a stockier look than that flats, where the biggest swatch of color is from the knees to almost the toes (although here visually complicated by the straps). Heeled sandals with thin straps would be even more streamlining, as they’d show more continuous skin and also give a height boost (see photo below, taken before the pictured sandals died but with a different angle and lighting)


Observation 2: More visual elements like color change, angle change (i.e. 90 degrees change with feet flat on the ground), and width change in the same spot will emphasize that spot more. Shoes that cut off exactly at the ankle also end up emphasizing sections because they put an additional visual element (color) in the same spot that already has two other dimensions of change (angle and width).

Guideline: A shoe with a high vamp and a low shaft that hits around the anklebone (like an oxford or a 3″-4″ shaft bootie) will look more lengthening with a heel, not just because it literally gives you more height, but because it decreases the other factor that emphasizes the “parts” of the leg: the angle that your feet stick out. I find that even a 2″ heel makes a difference and with a block heel is easy to get around in.

Aside: It seems like over the past couple of years, ankle boots with high shafts have moved into style at the same time as cropped length pants and midi skirts. So it makes sense to me that when pants go shorter and we moved from mostly maxis and minis to include a decent share of midis in stock in popular brands, the boot style would shift to suit that!

“But I don’t have the money, time, or space to have a dedicated shoe for each of my midi skirts!”

Well first of all, we’re going to cheerfully do the best we can with what we have and no one is going to declare you have to stay at home if you haven’t achieved Legs For Days. Choose the better of your two (or three, etc) options and rock it.

Second of all: socks.

I think these oxfords are actually not chunky enough of a shoe to balance these thick socks (something like a Dr Martens 1461 would be better), but you get the idea. You can get the same effect as a boot with a higher shaft by adding a sock. A sheer sock or a thin trouser sock would fit better here.


Three ladies who have better sock-shoe-pairing game than I do. Sourced from the unfortunately attributionless pit that is Pinterest.

Further reading: Extra Petite on skirt silhouettes

Hopefully that made sense! Let me know if this post useful or at least interesting, or if you want more of this type of content (although, I’ve spent much less time thinking about styling other items of clothing, so I’m not sure any subsequent posts would be quite as thorough or helpful, since I’m not Great At Hats or Great At Tucking In Shirts, etc).


4 thoughts on “Styling Midi Skirts

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