The Awkward Girl’s Guide to Midi Skirts

Want to know how to wear a midi skirt? Read on…

Midi skirts. So elegant. So stylish. So exactly like something Audrey Hepburn might wear…

… right up to the moment you look in the mirror, and discover that the midi skirt you thought would look SO chic hasn’t magically turned you into Audrey, Ultimate Style Icon. No, your midi skirt has only gone and transformed you into Audrey, the little old lady from down the road, instead. She’s 92, you know. And she’s got no time for all this ‘fashion’ nonsense, let me tell you, because she’s got to get to the shop before it closes, and buy young Jimmy some kippers for his tea, and… wait, where was I?

Oh yeah: midi skirts. They’re awkward, is what I’m trying to say here. Or they CAN be. In the wrong hands, they can end up looking downright frumpy, in fact, and that, my friends, is what I’m here to help you with today. Well, I’m going to try, anyway: I just want to be clear here that I in no way consider myself to be an expert on the dark art of midi-skirting, but I do get quite a lot of comments from readers who say they’d like to wear some of the skirts I’m always prancing around in, but are worried they’ll make them look super-short, or stumpy, or like Queen Elizabeth II on a bad day. God, it’s horrible the things people say about themselves, isn’t it? (Not the Queen Elizabeth thing, obviously: I mean, her Madge is stylin’.)

If you’re one of those people, then, this post is for you, and is here to show you that yes, you CAN wear a midi skirt: even if you think you’re too short, or too round, or too whatever-it-is that’s holding you back. Because if I can do it, anyone can: trust me on this. So, first things first:

CHOOSING YOUR MIDI SKIRT OUTFIT

So, the first rule of midi skirts is that you don’t talk about midi skirts. No, wait: that’s Fight Club, isn’t it? OK, the first rule of midi skirts is that they’re not all equal, which means you must choose your skirt with care, and probably get it tailored to make sure it fits you properly. Because here’s the thing: a true midi skirt (like they used to wear back in the Olden Days) should ideally hit around mid calf – hence the name “midi”. We’re not going to do that, though, and the reason is that this is not a flattering place for a skirt to hit. I

‘m not saying it can’t be done – pretty much ANYTHING can be done, if you have the right attitude – but it’ll be tricky, and why would you make things tricky when you don’t have to ?

The thing is, you don’t actually NEED to wear a mid-calf-length skirt to get the effect of a midi, though: a slightly shorter skirt will create the same kind of effect, but be much easier to style, which is why most of the “midi” skirts you see me wear hit just below the knee, rather than at mid-calf.

Most of them have also been altered to get them to that length: the one I’m wearing in the photos below (Collectif’s ‘Leisel’ circle skirt, if you’re wondering) is one of the few exceptions to this rule, but the vast, vast majority of midi skirts available on the high street right now will come almost to my ankles, so they have to go for the chop before I can wear them.

My first two tips, then, are these:

01.
IT’S ALL ABOUT PROPORTION – Midi Skirt Length:

if the mid-calf look isn’t for you, try going a little bit shorter. As long as your skirt is longer than average, people will still see a “midi”, so you’ll get the effect you’re after without feeling like you’re in a costume drama.

02.
YOUR TAILOR IS YOUR BEST FRIEND.

Or your sewing machine, if you have one. (My dog is actually my best friend, but that has nothing to do with midi skirts, so…) If you can sew, taking up a hem will be child’s play for you: if you can’t, it shouldn’t cost much to have it done for you, so hit up Google and find someone who can do the deed.

So, you have your perfectly hemmed midi skirt. Now what? Well, now comes the fun part: working out what to wear with your awesome new midi skirt. Below, you’ll find some quick tips on what to wear with a midi skirt: before you read them, though, I just want to re-iterate that these are tips, not rules. There ARE no actual “rules” when it comes to personal style, so these are just the tips I’ve personally found most effective when styling midi skirts: I’m not going to come and hunt you down or anything if you don’t follow them.

Let’s take it from the top: literally, I mean…

WHAT TOPS SHOULD YOU WEAR WITH A MIDI SKIRT?
Hoe to Style a midi skirt?

Working out what kind of top to wear with your midi skirt is actually pretty simple:

As you can see, Amber on the right of this photo has obviously been spending a bit too much time on Pinterest lately. She’s been looking at all the photos of cool girls in full skirts and slouchy sweaters, and she’s decided that she could be one of those girls, too. She’s wrong about that, though: and Amber-on-the-left knows it. That’s why she’s smiling smugly: because Amber-on-the-left knows what you’ve all long suspected – that those Pinterest girls are magical fashion unicorns. They don’t actually exist outside of Pinterest, and if you try to copy them, you’ll just end up looking like Amber-on-the-right, and you don’t want that, do you?

This tip is one that most people probably know, and it basically says that if you’re wearing volume on the bottom, you can’t ALSO have volume on the top, and vice-versa. If you, too, are a magical fashion unicorn, you might just be able to pull it off, but if you’re just a regular person like me, you’ll probably find that circle-cut midi skirts will look better worn with a top that’s both fitted and cropped (or tucked, in this case). You need to define the waist to make the volume work, basically, so anything that can be described using the words “slouchy” or “oversized” is best left to the Pinterest girls – or worn with a midi skirt that’s more fitted:

This tip is one that most people probably know, and it basically says that if you’re wearing volume on the bottom, you can’t ALSO have volume on the top, and vice-versa. If you, too, are a magical fashion unicorn, you might just be able to pull it off, but if you’re just a regular person like me, you’ll probably find that circle-cut midi skirts will look better worn with a top that’s both fitted and cropped (or tucked, in this case). You need to define the waist to make the volume work, basically, so anything that can be described using the words “slouchy” or “oversized” is best left to the Pinterest girls – or worn with a midi skirt that’s more fitted:

Even then, I’d still want to tuck it, to create the illusion of a waist:

This simple little “front only” tuck is a really easy way to emphasise the waist, and make the overall look a little more polished, without having to tuck tons of fabric down the front of your skirt, which, AWKWARD.

volume on the top = no volume on the bottom. (EDITED TO ADD: In the years since this post was written, the ‘slouchy top + midi skirt’ look has become quite fashionable, which makes it much easier to wear, because it’s a look that people are pretty accustomed to seeing these days. That makes this piece of advice feel a little bit redundant – and me feel a bit stupid, really – but I can’t go back in time and change it, so moving on…)

WHAT SHOES TO WEAR WITH A MIDI SKIRT?

This is another fairly easy one, and I’ve made a handy graphic to illustrate it:

By which I mean, “ditch the ankle straps”. Shoes with ankle straps can be almost as tricky to wear as midi skirts themselves, as, like midi skirts, they have a tendency to shorten the leg. (Visually, I mean, not literally.) See how these shoes draw a line across my ankle, effectively dividing the leg into two halves, and making it look a bit shorter? The long hem of the skirt is doing that already, and I don’t need any help to make my legs look shorter, so while I will occasionally wear ankle straps (like I said, there are no “rules” here…), for the most part I try to avoid them with longer skirts. Speaking of things that shorten legs…

HOW TO WEAR A CALF LENGTH SKIRT with flats

A lot of people think they shouldn’t wear flats with a midi skirt, citing the “but they’ll make my legs look shorter!” rule as evidence of this. Now, there’s no getting away from the fact that flats will make your legs look shorter, and so will midi skirts, so if making your legs look longer is your goal, then yeah, stick to heels. There’s also no getting away from the fact that heels aren’t always practical, though, so, again, it’s all about proportion. As long as your skirt isn’t super-long, you should still be able to wear flats with it: my rule of thumb here is to go for pointed or almond toes rather than round ones (pointier toes will lengthen the appearance of the foot, and therefore the leg), and if I’m going to be wearing flats, I’ll normally try to pick a slightly shorter skirt. Oh, and no ankle straps – again!

But what about boots, I hear you say! I’m glad you asked…

HOW TO WEAR A MIDI SKIRT with boots

When it comes to boots…

Ankle boots with bare legs makes for a very trendy look, and you’ll see the Pinterest girls do it all the time. They’re magical unicorns, though, remember? When I try to do it, it just doesn’t look right: that doesn’t mean it won’t look right on YOU, you magical unicorn of a person, but when I’m wearing boots with a midi skirt, I always make sure the hem of the skirt covers the top of the boots. Again, this is to prevent that whole “dividing up the leg” thing I keep banging on about. Another way to do it is to pair your ankle boots with tights of the same colour:

It’s much less trendy, but then again, I’ve never claimed to be trendy, so no surprises there. (Oh, and it’ll be warmer than bare legs, too!)

Finally: outerwear!

MIDI SKIRTS AND OUTERWEAR: WHAT TO WEAR WITH A MIDI SKIRT

Winter can be particularly difficult for us midi-skirters, because not many coat manufacturers take midi skirts into consideration, unfortunately. There are basically two types of outerwear that work with midi skirts:

01. Very long coats, which cover the skirt entirely

02. Very short jackets, which leave most of the skirt exposed.

Oh, and if your midi skirt is a full one, your coat also has to be full, otherwise you end up with tons of fabric trapped inside a straight-cut coat, and that’ll be as uncomfortable to wear as it is awkward to look at. Here’s an illustrated guide:

Of this lot, the first coat works because it’s both long enough to cover the skirt and full enough to accommodate it. The second coat is what I call the “badly wrapped parcel” look: it’s too short, so the skirt sticks out underneath: it’s not the worst look in the world, but I always think the two different hems look a little messy, so it’s one I try to avoid. The white jacket is also too short to cover the skirt, but because it’s SO short that it leaves most of the skirt exposed, it works better than the coat. The biker jacket is better still, because it’s short enough to show almost all of the skirt, while the green coat is… just everything that’s wrong with the world, really. (When worn with the skirt, I mean.) It’s both too short AND too narrow, so it’s turning my body into a rectangle, and trapping the skirt underneath it: it’s the worst of all worlds, basically.

Where to shop for calf length skirts

Since this article was written, skirts like the ones pictures have become a little harder to find. Don’t worry, though, midi devotees: you can still find your favourite length of skirt (in fact, there are more of them around than ever), it’s just that, these days, it normally comes attached to a dress of some description, and will tend to be little longer, and less “retro” in shape than the one I’m wearing here.

The good news is that, regardless of what your skirt/dress looks like, the same “rules” still apply. At the time of writing, it’s become fashionable to wear what I’d personally call unflattering shoes with dresses and skirts of all descriptions (think Birkenstocks, sports shoes, clumpy boots) so, if being “on trend” matters to you, you might want to disregard some of the footwear tips I’ve given above, but most of the other tips hold true, even several years after this post was first published.

Here’s how I normally wear my midi skirts:

And now you know everything *I* know about how to wear a midi skirt. If there’s anything I’ve missed, drop me a comment!

What is a midi skirt

A midi skirt is a type of skirt that falls midway down your calf, between the knee and the ankle. The term “midi” refers to its mid-calf length, which distinguishes it from mini skirts, which are significantly shorter, and maxi skirts, which typically go down to the floor. Midi skirts come in a variety of styles, such as A-line, pencil, pleated, and circle skirts, and they can be dressed up or down, making them a versatile piece for many occasions. They’re considered a timeless piece in women’s fashion, flattering a wide range of body types and suitable for both casual and formal settings.

Related: How to style a midi skirt in winter

Related: How to get used to wearing heels