Every September I put my midi skirts away with the sandals.
Every single year.
And every October I dig them back out, because they’re honestly the easiest thing I own once it gets cold.
I have 6 of them right now (don’t ask how many I’ve given away), and 3 of them get worn every week from October to March.
A midi skirt is just a skirt that ends somewhere between your knee and your ankle.
Most of them land around mid-calf.
That length is the whole trick for fall.
It covers more than a mini, so you’re warmer.
But it still shows a little leg or a little boot, so the outfit doesn’t look heavy.
Not sure where a midi will hit on you? The free dress length chart turns your height into the length to buy.
I’m not a stylist, just a fan who plans her outfits the night before.
Here are the six fall midi looks I keep coming back to, and the shoe rule that makes them all work.
1. A Pleated Midi, a Black Sweater and Chunky Boots
Mint pleats, a plain black sweater, chunky black ankle boots.
That’s it.
That’s the outfit.
The reason it works is the contrast.
The skirt is light and swishy, the boots are heavy.
Put this skirt with a dainty flat and it reads like a summer wedding guest.
Put it with a lug sole and it’s suddenly a fall outfit.
Keep the sweater short or tuck the front in.
A long, loose sweater over a full skirt hides your waist, and then everything just looks like one big shape.
I learned that from the photos of my cousin’s birthday dinner, where I looked like a very cozy bell.
A sweater that ends 2 or 3 inches below your natural waist is about the most you can get away with untucked.
For color, black looks great with mint, rust, camel or burgundy pleats.
All black (skirt, sweater, boots) is lovely too, but add one thing with texture, like a ribbed knit or a leather belt, so it doesn’t go flat in photos.
I have a whole post on pleated skirt outfits if this is your kind of skirt.
2. A Floral Midi With a Denim Jacket and White Sneakers
This is my “it’s 48°F in the morning and 70°F by lunch” outfit.
You know those days.
The jacket comes off around 11, gets tied around my bag, and goes back on at 5.
A summer floral skirt keeps going into October if you add a denim jacket and swap the sandals for white sneakers.
The jacket should be short, ending at your waist or just above it, so the skirt still gets to show off.
Red and denim blue are an easy pair.
This whole outfit costs nothing new if you already own a jean jacket from 2019 like I do.
If your print has a lot of colors, pick one of them for your top and let the jacket do the rest.
Not into red?
The same trick works with a navy or forest green floral, and a darker print looks like fall from the start.
Swap the white sneakers for brown ankle boots once the leaves come down, and this outfit keeps going until Thanksgiving.
I wrote more about denim skirt outfits for when you want the denim on the bottom instead.
Which Shoes Go With a Midi Skirt?
This is the part people get stuck on, and it’s mostly about where the hem lands and where the shoe stops.
The one thing to avoid is a boot that ends right where the skirt ends, or just a sliver below it.
Your legs disappear and it looks like a mistake.
Either leave a gap of leg (or tights) between the two (I like at least 2 inches), or go with a tall boot that slides right up under the hem.
This photo is the gap done right.
Rust pleats, sleek black ankle boots, and a clear band of leg in between, so the boot looks like a choice and not like it slipped down.
Check it in the bathroom mirror before you leave, and actually walk 10 steps.
A midi moves, and the gap you see standing still changes when you walk.
Loafers, ballet flats and mules all count as low shoes here, and loafers are what I wear most on work days.
They look best with a bit of bare ankle or a sheer black tight showing.
Anything that stops at the ankle wants some leg above it, never a chunky sock bunched up under the hem.
3. A Bright Striped Midi and a Plain White Tee
When the skirt is loud, everything else gets quiet.
A plain white tee, simple shoes, hair up.
Done.
I love that she went with a messy bun and big earrings here.
When the neckline is a plain crew, the earrings are what pulls your eye up to your face.
For real fall weather, swap the tee for a thin cream sweater and add tights in a color from the stripes.
A rust or mustard pair looks so good with a skirt like this.
Tights are sold by denier, and the higher the number, the thicker the yarn.
Most brands call 60 and up opaque, so that’s what I wear once it’s properly cold.
A 40 pair is my in-between for October (a little color, a little leg showing through, and no sweating by noon).
4. A Long Pleated Skirt, a Printed Blouse and Sneakers
If you like more coverage, this is such a pretty way to do it.
The skirt runs a little longer than a true midi, closer to the ankle, and it’s still light and easy.
The colors are what make it.
Beige skirt, a peach scarf, and a blouse with a small print that has both of those colors in it.
Nothing fights.
The white sneakers keep it comfy for a day of walking.
If you’re going somewhere dressier, a low block heel (2 inches is plenty) works with this length too, and you won’t sink into grass the way you would in thin heels.
Once the mornings turn cold, I’d put a camel cardigan over the blouse and trade the straw hat for a beret.
Camel sits right next to beige, so nothing new has to match.
5. A Midi Skirt With Knee-High Boots
This is the one I reach for from November on, when it’s 34°F at 7 a.m. and there’s frost on the car.
No leg shows at all.
The boot goes up under the hem, so the skirt and the boot overlap and your whole lower half reads as one long line.
It’s the second branch of the shoe chart above, and it’s the warmest way to wear a skirt that I know of.
Over-the-knee boots like the ones in the photo work the same way, and they’re even warmer.
If your skirt has a slit, a tall boot covers the leg it shows, which is a nice bonus on a windy day.
Check the overlap sitting down, too.
A skirt that covers the top of the boot when you stand can ride up 2 or 3 inches in the car, and then you get the awkward gap anyway.
(Ask me how I know.)
A sleek leather or suede boot looks best with a full, swishy skirt.
Slouchy boots are great with a straighter skirt, but slouch plus pleats is a lot going on below the knee.
On top I keep it fitted, a ribbed turtleneck tucked in or a short sweater.
If you add a coat, go either short (waist or hip) or long enough to cover the hem.
A coat that stops a few inches above the hem cuts you off right where the skirt is busiest.
6. A Satin Midi and a Chunky Knit
People think of a satin slip skirt as a summer thing, or a wedding thing.
In fall it’s my favorite way to look dressed up without trying very hard.
The trick is the same one as outfit 1: put the shine right next to something rough.
A cable knit or a wool coat.
Shiny next to nubby, and each one makes the other look better.
Mine is plain black satin, and the floral slip skirt in the photo works exactly the same way under a blue-gray cable knit.
Satin shows every bump, so I never tuck the whole sweater in.
Just the front, or a sweater that ends right at my waist.
Shoes go either way.
Ankle boots keep it casual for a Saturday, and a loafer or a pointed flat makes it work for dinner.
One warning from experience: satin plus tights plus dry winter air means static, and the skirt will cling to your legs all day.
A slip under the skirt helps, and so does a little lotion on your legs before the tights go on.
Satin also creases if you sit for an hour, so I hang mine in the bathroom during a 10-minute shower and the steam takes most of the wrinkles out.
The Fall Midi Formula
If you only remember one thing, it’s this: something fitted on top, the skirt, a short layer, and a shoe that’s either clearly below the hem or clearly under it.
I taped this to the inside of my closet door for about 4 weeks.
Now I don’t need the note, which tells you how simple it is.
And if your skirt is so long that you’re stepping on it on the stairs, it’s not the outfit, it’s the length.
That’s the one fix a tailor can do in a day, and a plain hem is one of the cheapest jobs they take.
Mine was $18 last year.
Want more cold-weather ideas?
My knit sweater outfits post pairs really well with all six of these.
I lay mine out the night before, take a quick look, and I’m getting ready in about 5 minutes the next morning.
Which, on a Monday, is everything.
