Style Notes: Pairing shoes with midi skirts

midi skirts style notes header

This is a new and improved version of one of my earliest blog posts! I hope these tips and examples are useful for those looking to fine-tune their own midi skirt outfits, so you can create exactly the look you want!


Elements that create vertical emphasis or horizontal emphasis

Keeping these in mind, I can tweak the silhouette or vibe of an outfit based on what I want to achieve.

For example, if I want to use round toe footwear for a more grounded and less dressy look, but I want to balance out some horizontal emphasis from the skirt’s silhouette, I can choose an OTK boot or wear matching tights to keep my lower leg and shoe section as a single visual unit and the visual flow of the whole look is a little smoother

vertical emphasis horizontal emphasis
pointed toe shoes round toe shoes
low vamp shoes (e.g. flats) high vamp or strappy shoes
fitted boot shaft loose boot shaft
streamlined sole chunky sole
continuous color colorblocking
fitted skirt silhouette flared skirt silhouette
slinky or choppy skirt clean cut skirt

Colorblocking and flared, clean cut skirts are under horizontal emphasis because they create additional segments in the outfit and emphasize the proportions, more-so than elements that work towards a streamlined or columnar effect.

These can be used to create fun silhouettes and contrast, but the segmenting created by the horizontal elements will emphasize the outfit proportions, so if those are off it can look more awkward than the same proportions in a more streamlined silhouette.

Adding visual weight

In the most general terms, anything that contrasts with the surrounding elements. But a little more concretely:

  • Stuff that literally takes up more space (thank you, I’ll be here all week)
  • Light colors (if surrounded by dark colors) / bright colors (if surrounded by muted colors) [1]
  • Prints (bolder prints have more visual weight than smaller or less defined prints) [2]
  • Contrasting textures – for example, the same shoe in shiny patent leather will draw the eye more than the same one in matte leather. Gathers, ruffles, pleats against smooth fabrics.
  • Hardware detailing (studs, zippers, lace-up closures, etc.)

These elements will emphasize whatever part of the outfit they are on, drawing the eye and making the area appear to take up more space.

These are just things to consider, not a a “do X not Y” style proclamation. There are so many other factors in styling something, and it isn’t always about just looking as willowy as possible.

For example, if you have a floral print but otherwise low-profile dress that you want to pair with sneakers, if you want the dress to be the star of the outfit, you could go for a lower-profile pair like Keds, Vans, or Converse.

If you’re going for an eye-catching look with head-to-toe visual interest, you could combine a brightly colored, ruffle midi dress with a pair of chunky dad sneakers and bold accessories.

(Tbh I don’t actually think following photo is of a midi dress, which I usually think of as calf-length. But it’s no fit-and-flare or bodycon mini.)

I like how the heavy shoes here emphasize the triangle silhouette by continuing the visual weight at the bottom.

Why are midi skirts harder to style?

I couldn’t find any articles to back this up, but personally, I think it’s because there’s less of a buffer zone between the skirt segment of the look and the lower leg / shoe, so any part of the proportions or visual weight that’s off is a lot more noticeable. Horizontal elements will also play off of each other more strongly.

I’ve seen people lament that they can’t wear midi skirts at all because they’re short. That’s definitely not true that height is totally prohibitive, as midi skirts looking conventionally attractive comes down to the proportions and not the overall height. However, I concede that having less space to work with vertically presents more of a challenge, as there isn’t as much of a buffer zone when it comes to flattering lengths of particular items in an outfit.


These aren’t meant as a prescriptive It presentation of “the right way vs the wrong way” to style things, but just provide a visual demonstration of the concepts described above. Depending on what look I want to go for, I could happily wear any of these out.

Much of the commentary is subjective, but the point is that you can take note of many different details of your outfit and be mindful of how they make you feel, which is the important thing. These are just examples of how I might weigh options.

I don’t know that this is the most flattering angle/pose/styling for my hair, as with the poor resolution it’s starting to go into bowl cut territory in some photos, but I wanted to have a clear delineation between my hair and the dark top, so I pulled it back.


Combat boots

Three very slight variations in skirt against docs. On the left I’ve clipped the skirt back to get more of a pencil dress shape just as a demo, and the skirt on the right is a tiny bit shorter (hitting at a wider part of the leg) and has gathers all along the hips instead of a few large pleats.

The center outfit emphasizes the chunkiness of the boots. To me the gestalt is more segmented like bam skirt hem and then bam boots, versus the left outfit in which the boots feel more like a bookend for the skirt, since the soles are about the same width as the skirt itself, and the tapered silhouette also helps keep a smooth rhythm to the outfit (see a comparison of tapered vs untapered skirt over on the Extra Petite blog).

The look on the right is a softer, stockier look since there are so many elements with more of a horizontal emphasis, notably the gathers towards the waist, which give the skirt its volume.

I like the contrast between the more vintage-inspired silhouette of the center outfit with the docs, though the sleeker modern take on the left is also fun.

midi skirt docs swap skirt

  • Uniqlo “women ribbed high-neck long-sleeve t-shirt” (via Poshmark)
  • Uniqlo x Ines de la Fressange 2018 corduroy button-front midi skirt
  • Uniqlo x Ines de la Fressange cotton gather skirt (I got this taken up because I found my feet would catch on the hem while walking quickly, but unfortunately 1-2″ too high for my preferred proportions)
  • Dr Martens 1460 boots in smooth leather

No side-by-side for this one, but here’s an example of a dress in a slinkier/drapier fabric with a less defined hem. There really isn’t much horizontal emphasis anywhere in the outfit aside from the boots, so the overall effect is pretty streamlined and fluid.

desert sci fi handkerchief hem dress docs

  • Dr Martens 1460 boots in smooth leather
  • Forever 21 chenille handkerchief hem dress, Five and Diamond mesh opera glove, Amazon utility bag

Flat sandals

Again, here are the two slight variations of skirt, but with sandals.

While the gathered skirt is a wider look, I like how the gathers draw the eye upward and anchor the visual weight in the middle of the outfit, rather than the right side which kind of funnels everything to the shoes, which are not that interesting and kind of seasonally disjointed from the high coverage mock neck and corduroy. I think a wide brimmed sun hat would look cute, especially with the left outfit which is more springy to begin with since the skirt fabric is lighter.

midi skirt sandals swap skirts

  • Birkenstock “Mayari” sandals


A high visual weight skirt

The dense daisy print and layered ruffles becomes the focal point of most outfits it’s in.

floral ruffle midi skirt shoe comparison

The space buns outfit on the left, while not the most conventionally attractive silhouette of the lot, leans more into a 90s aesthetic and has more personality than the plain pointed toe boots. However the center outfit would be a good option for some event where I felt I should look nice, but didn’t have the energy to wear something distinctive.

I think the ruffles are a little heavy for my ideal version of this particular outfit, since as-is they’re competing with the boots. I wonder if a more extreme chunky platform combat boot would look better. My suspicion is that at that point, I would also end up wanting a louder element in the top half of the outfit to balance things out.

It’s not bad by any means, but I find that the many straps of the pointy flats are a similar scale of detail to the skirt, and having them next to each other kind of mutes some of the interest the items would bring when placed next to a solid colored item.

This is my personal favorite outfit with this skirt, although I didn’t manage to get a neutrally posted photo of it. The lower vamp feels airier and leans into the springy aesthetic, while the sharp silhouette of the shoe still isn’t overwhelmed.

floral ruffle midi skirt with pumps

(The show that night included several Macbeth style witches.)

  • Reformation “Vita” blouse
  • Chicwish daisy ruffle skirt (via consignment)
  • Dr Martens 1460 smooth leather
  • Steve Madden “Jaclyn” bootie
  • Halogen “Kali” flats
  • Franco Sarto “Coralie” pump in black

Straps vs low vamp; Round toe vs pointed toe

Here’s a direct comparison of the effect of horizontal detailing on otherwise similarly shaped shoes. The center look with the low-heeled pumps has a cleaner visual line down the leg and foot. The strappy flats create a shorter leg line as they break it up, although the high contrast does spotlight the shoe.

The sandals don’t have the elongating pointed toe, so the overall effect is a shorter leg line, but the skin tone visible through the foot keeps the line going somewhat and has a lighter feel to me than the multiple smaller straps.

midi skirts black shoes and sandals

  • Franco Sarto “Coralie” pump in black (this has an ankle strap, which I tucked in for demo purposes here)
  • Birkenstock “Mayari” sandals
  • Halogen “Kali” strappy pointed-toe suede flats

Flat vs platform; monochrome vs contrast

Two round shoe options. These clogs are great for any outfit where I feel I want a longer leg line, since the platform literally adds height, but is also similar to my skin tone, so the monochrome effect preserves the vertical flow along the legs vs a different colored shoe of the same type.

I don’t think the extra length is make or break for this base outfit, but I do feel that the clogs’ slightly higher level of dressiness and sturdiness suit it a little better.

midi skirts platform clogs vs sandals

  • MIA “Madeline” t-strap platform clogs
  • Birkenstock “Mayari” sandals

Boots: pointed toe vs round toe

The shafts of these lace-up boots come up to a similar spot. I like both these outfits equally, they just give off different vibes. The shiny patent pointed toe boots are more feminine and slightly dressy, while the docs give a cool get-stuff-done utilitarian spin on the look that I think works due to being complemented by the unfussy top.

midi skirts pointy boots vs combat boots

  • Dr Martens 1460 boots in smooth leather

Pointed toe: shoe vs high shaft ankle boot

These both have pointed toes, but demonstrate the differences that the shaft/vamp height and stripey detailing make when it comes to height. Ideally I would have had flat boots for the most direct comparison, but these do have a short heel on them.

midi skirts pointy boots vs pointy flats

  • Marc Fisher “Bowie” boot
  • Halogen “Kali” strappy pointed-toe suede flats

Pointed toe shoe: tights vs no tights

Tights and socks are a great way to play around with the proportions of footwear, without having to get more footwear. For example, using socks to create more of a boot-like silhouette and change the proportions to more of a two-part skirt + shoe with a bit of negative space at the leg, vs a full three segment skirt + calf + shoe when the footwear breaks off exactly at the ankle.


Here I wore black tights under one of the shoe options with the most horizontal emphasis. The flow of the outfit feels really different, although the vibe is also changed to one that’s more winter-y and modest.

midi skirts strappy flats tights vs bare

  • Halogen “Kali” strappy pointed-toe suede flats

Round toe boots: ankle vs OTK

One of my favorite “hacks” for days when I don’t want to deal with shoe proportions is to just wear tall boots. Then it’s just one segment! It’s like the fall/winter equivalent of the blogger-favorite footwear of minimal nude tone high heeled ankle strap sandals.

The ankle boots create more of a cute, youthful effect since I find their overall silhouette is rounder and more playful.

midi skirt otk boots vs ankle boots

  • Jeffrey Campbell x Free People “Joe” lace-up boot in taupe (via Poshmark)
  • Comfortiva “Cordia” lace-up ankle boot in caffe

I only have a so many selections of skirts and shoes that I can personally demonstrate with, but hopefully that all showed that with a few quick photos and a side by side comparison, you can easily analyze which details in your own outfits and have more confidence that your look comes across to your preferences.

If you wear midi skirts, what skirt-shoe combo is your favorite to wear? What elements of it do you particular like?

You might also like

  • Styling modest vintage-inspired pieces to feel less old-fashioned
  • A 2013 paper by Beck and Savazzi exploring the effect where taller people are perceived as being thinner than shorter people of the same width, and how the effect persists in silhouettes and cylinders but seems to be strongest in full images of people. I’m not linking to this to argue that everyone needs to dress to look as tall and thin as possible, but the general discussion section of the paper had some interesting points on why this perception happens.


  1. Thank you for sharing that link to the paper on the tall/thin illusion! It’s interesting to see the effect was stronger on humans than just rectangles. I love tying in stuff from other fields to fashion, too.


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