How to Style a Midi Skirt: 12 Outfits for Every Season
If I could only keep one type of clothing, it would be the midi skirt. It is the backbone of a modest wardrobe, it works in every season, and it can be casual or dressy depending on what you pair it with. But because it is such a basic, it is also easy to get stuck wearing it the same way every time.
Here is how I style the four kinds of midi skirts most of us own, with outfit ideas for every season.
First, find your best length
"Midi" covers a lot of ground, anywhere from just below the knee to just above the ankle. The most flattering spot is usually the narrowest part of your calf, or a little below. If a skirt hits at the widest part of the calf, it can make the whole outfit feel heavier.
Not sure? Stand in front of a mirror with a skirt you love and note where it falls. Measure it from waist to hem and use that number when you shop online. Most product pages list the length.
The satin (slip) midi
A satin midi is the most versatile skirt you can own. It is soft and fluid, it catches the light, and it makes even a plain sweater look elegant.
Fall: a chunky cable-knit sweater, loosely tucked at the front, with loafers or ankle boots.
Winter: a fine turtleneck, long wool coat and knee-high boots. Add opaque tights underneath.
Spring: a fitted tee or a thin cardigan buttoned as a top, with ballet flats.
Summer: a simple short-sleeve knit top and flat sandals.
Tip: satin can cling, so a thin half-slip makes it hang better and keeps it from getting static in winter.
The pleated midi
Pleats move beautifully and feel a little more polished than a slip skirt. Accordion pleats are light and flowy; box pleats have more structure.
Fall: a merino crew sweater and pointed flats.
Winter: a blazer over a turtleneck with heeled boots. Very office friendly.
Spring: a striped button-down with sneakers for a relaxed weekend look.
Summer: a sleeveless shell layered over a fitted tee in a matching color.
Keep the top fitted. Pleats add volume at the bottom, so you want a cleaner shape at the top.
The denim midi
Denim skirts are the everyday workhorse. They are sturdy, easy to wash and hide wrinkles.
Fall: a chunky cardigan, a striped tee and loafers.
Winter: a grey sweatshirt-style knit, wool socks and lace-up boots.
Spring: a crisp white button-down, sleeves rolled, with white sneakers.
Summer: a linen top in a soft color and leather sandals.
Look for heavier denim with a little stretch. Thin denim tends to cling to the legs and doesn't hang as nicely.
The knit midi
A ribbed or sweater-knit skirt is the coziest option. Wear it with a matching sweater as a set and it feels like a dress.
Fall: a matching knit top for a tonal set, plus sneakers.
Winter: an oversized sweater and a long puffer or wool coat. Basically winter pajamas that look like an outfit.
Spring: a cotton button-down left untucked, with mules.
Summer: better to switch to a lighter fabric, but a fine-gauge cotton knit skirt can work on cooler evenings.
Shoes that work with midi skirts
The shoe changes the whole feel of a midi outfit.
- Pointed flats are my top pick. They lengthen the leg and work from morning to evening.
- Loafers look a little preppy and are perfect with pleats and denim.
- Ankle boots with a small heel work best when the skirt hits mid-calf or lower, so there isn't a big gap of leg.
- Knee-high boots that disappear under the hem are great in winter.
- Sneakers make dressy skirts feel casual and modern.
- Mules or kitten heels are lovely for events.
Tops: tucked, half-tucked or cropped
Because midi skirts usually sit at the natural waist, a long untucked top can make your legs look shorter. Three easy fixes:
- Front tuck a sweater or shirt.
- Choose a slightly cropped knit that ends right at the waistband.
- Add a belt over a top or cardigan to define the waist.
For modest dressing, a cropped knit over a fitted long-sleeve layer works well. It shows the waist line without showing anything else.
Layers
A long coat that ends just above or below the hem of the skirt looks very elegant. A shorter jacket (a cropped blazer, a denim jacket, a quilted jacket) that ends at the waist also works. What doesn't work as well is a coat that ends right at the hip, because it cuts the outfit in an awkward spot.
Build your skirt rotation
If you are starting from scratch, I would collect skirts in this order:
- A neutral satin midi (champagne, black or chocolate).
- A dark denim midi.
- A pleated midi in a color you love.
- A knit midi for winter.
With those four and a handful of knits and tees, you can get dressed every day of the week.
You'll find my current skirt favorites on the Skirts page and more outfit ideas in 10 easy fall outfit formulas.
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