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The Awkward Girl’s Guide to Midi Skirts and How to Wear Them

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

How to wear a midi skirt

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:


black midi skirt and stripe bardot top with red shoes



o, 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.

what to wear with a midi skirt

My first two tips, then, are these:


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.


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…


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

: choosing the right style of top to wear with a midi skirt

what top to wear with a midi skirt
what top to wear with a midi skirt

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:

The Awkward Girl's Guide to Midi Skirts and How to Wear Them

what NOT to wear with a midi skirt

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:

tucking a sweater into a skirt at the front only is an easy way 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. 

stripe top with tuck 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…)


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

style advice: what kind of shoes should you wear with a midi skirt

what shoes to wear with a midi skirt

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 style a midi skirt with flats

can you wear flats with a midi skirt?

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…


When it comes to boots…

what kind of boots should you wear with a midi skirt

what boots to wear with a midi skirt

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:

how to style a midi skirt with ankle boots

midi skirt and tights

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!

what kind of coat should you wear with a midi skirt

What coat 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:

how to wear a midi skirt with coats and jackets

what coat to wear with a midi skirt?
How to Wear a Midi Skirt With Outerwear

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.

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!

how to wear a midi skirt: an illustrated guide

how to wear a midi skirt - and how not to wear one

How to wear a midi skirt: styling tips

styling tips for midi skirts

What do you think?

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  • Hana
    November 12, 2015

    Oooh I love this article! It’s so great to see how different shoes and tops look with midi skirts, and I think you nailed the perfect look – but I bet you’ve had a lot of practice with all those beautiful retro dresses 🙂

    • Shirl SW
      April 2, 2019

      Hurrah for mentioning flats! We can’t all totter about in vertiginous heels, yet fashion bloggers go on and on about the spindly heeled foot torturers like we should all wear them! I prefer to be able to get from a to b and back again without spraining something!

  • Daisy
    November 12, 2015

    Fab advice, very helpful 🙂 Now if you could do this for every type of clothing I’d have a handy how-to-wear-clothes guide and my stylish mum and brother wouldn’t criticise my (lack of) dress sense!

    • Amber
      November 12, 2015

      I was actually thinking of doing some other ones in a similar style, so I’m really glad you liked it! If there’s anything specific you’d like a guide on just say and if I’ll do my best! (Assuming it’s something I actually know about, obviously!)

      • Aparna
        November 16, 2015

        Please do that! Your pictures look great, and your tips make sense.

  • Media
    November 12, 2015

    Hi Amber, love the article! Would you say these tips also apply to long coats, like the princess coat? I’d love to get one, especially those with faux fur on the hem and cuffs but since I’m so short (less than 160 cm), I’m not sure if I can pull it off or if it won’t look to costumey.

    • Amber
      November 12, 2015

      I think it really depends on the coat and where it hits on the leg: basically it has to look intentional, rather than just too big… This style of coat is designed to be pretty long (which makes it really easy to style, because you can wear absolutely anything underneath it!), but the key is to make sure it fits perfectly everywhere else, or it’ll just swamp you. A lot of people size up in coats to accommodate bulky sweaters, but then the coat itself can end up looking huge, so I go for my regular size (I would rather wear thermals than tons of layers, anyway) and have it tailored if it doesn’t fit properly. If you’re short, you need to pay particular attention to the shoulders and sleeves – I’m 5’4″, but I still find most sleeves super-long on me, and that kind of thing is what creates the “dressing up in mum’s clothes” look, so good tailoring is the answer to everything, basically. (With that said, these coats ARE a little costumey – it’s a “look” rather than just a coat, if that makes sense!)

  • Erin
    November 12, 2015

    Amber this is a great idea! The instructional guide style reminds me of reading fashion magazines in the 90’s, and the pictures are super helpful and cute. I also like the cheeky thumbs-up/thumbs-down photos. 🙂

  • CiCi Marie
    November 12, 2015

    Love this post – and also glad to see I’m following most of your ‘rules’ as I’m not a magical fashion unicorn either (putting it mildly). I do sometimes wear ankle straps with my midis though – but those tend to be with the shorter, more knee-length ones, yep. Problem is my feet are so narrow I largely need a strap on my shoes, so it can’t be all court shoes all the time over here 🙁 Anyway, you’re definitely right that the key to these skirts is so often – just get them to fit right, and pay someone to alter them if you have to!

    • Amber
      November 12, 2015

      I wear ankle straps too, sometimes: I think one of the most important things to remember is that you have to be realistic – life isn’t Pinterest, so sometimes you need to just wear the shoes that fit!

      • Loretta
        April 28, 2019

        Hi Amber I’ve a bright bright yellow midi skirt Wondering what color top you’d recommend with it fur a wedding? Cheers Loretta

  • jodie filogomo
    November 12, 2015

    I really like how you showed the yes & no versions!! Although I will disagree with you and say I liked that striped slouchy shirt with the pencil skirt when you front tucked it—I think it gave you a whole different personality and the lines were good!!! jodie

  • Gem
    November 12, 2015

    Can I ask for one on looking stylish while walking the dog please? Summer was fine, but now pup and I are walking in the rain more and more, and it’s getting colder. I’ve suddenly realised pup must think I live in my gym kit and husband’s waterproof coat (and so must my fellow dog walkers).

    • Amber
      November 12, 2015

      I actually do exactly the same – I just can’t bring myself to care what I look like when I’m battling a gale force wind, unfortunately!

      • Gem
        November 13, 2015

        Normally I wouldn’t mind but we live in a small community. Dog walks usually involve bumping into husband’s colleagues/bosses and/or their (immaculate looking) wives.

  • Brenda F
    November 12, 2015

    Thanks for this post, Amber! I had written off midi skirts long ago, but maybe will try again. I think everyone needs a good tailor, it’s amazing how they can turn frump into fashion with the shortening of a hem!

  • TinaD
    November 12, 2015

    This is a really good primer on proportion. I fell over a photo a while back of Christian Dior measuring a model’s hemline–I forget where–apparently it was supposed to be 40 cm from the floor in all cases, measured with the woman in shoes. I don’t know how that works out on normal people, because I can’t simultaneously wear my skirts and measure the hemlines, but it suggests shorter skirts for shorter legs, and also shorter skirts for flatter shoes, to keep the New Look proportions. (And I totally agree re:Pinterest; street stylistas appear to exist in a land without weather. Because otherwise, jeans+camelhair coat+strappy sandals=frostbite. Unless we’ve decided that “lost three toes” is the new sexy?)

    • Lena | Lena Talks Beauty
      November 15, 2015

      Stand on the bottom of a measuring tape? Or else rope in someone else for assistance.

    • Kirstin
      June 7, 2017

      I have seen this too! It finally made sense why the skirts always looked fabulous!

  • Anna
    November 12, 2015

    Hi Amber, that was a really thought-out well written post. The thing with midi – or even any other skirt the length is always come down longer as i’m quite short, so a midi could be a maxi on me and and a maxi could be a dress! If you get what I’m getting at. I still found the tips to helpful. xx

  • Heather
    November 12, 2015

    Gosh, could you be any cuter! This was fantastic, i loved LOVED the visual photos to go with the tips. So helpful!!!

  • Miss Kitty
    November 13, 2015

    Loved this article! Lots of helpful tips, thanks! Could you please please please also do one on accessorising (if that’s a word)? This is my total bugbear – I can put together a fairly decent outfit, but fall flat with my accessories. I would love to see how you do it! And also one on how to wear different winter coat styles and boots, seeing as I will be digging these out fairly shortly.

  • Andrea@WellnessNotes
    November 13, 2015

    I really liked this post! The side by photos are great!

    I saw in one of your replies above that you are thinking of doing more of these kinds of posts – that would be great!

  • Miriam
    November 13, 2015

    This is so helpful, thanks Amber! I’ve just bought my first full midi skirt (a tutu!), and was stumped what to wear it with. Your post came at the perfect time!

  • Jay
    November 13, 2015

    I actually really like the slouchy shirt/skirt combo on you.

  • Kate
    November 15, 2015

    I’m sure many will benefit from this post. The comparison photos are so cute, it must be very time consuming to do it.
    You always look stunning in pencil dress but it’s not for everyone. It’s very challenging to carry it off. How about choosing the right pencil dress for different body type?

    • Amber
      November 15, 2015

      Because I’ve only ever shopped for myself, I don’t think I’d have much insight to offer people with different body types: I was thinking more of the kind of topics I have some personal experience of!

  • Emily
    November 17, 2015

    Thanks for the work that went into this post, the advice is good and the photos are perfect illustrations.

  • Nini
    January 12, 2016

    Nice post, I love your tips, they make sense to me 🙂

    I was wondering, do you wear a petticoat underneath ? I like the volume a petticoat gives but it’s just too fluffy for me and really not practical for everyday (and it’s just two layers !). I guess I just need a bit of practice.
    Now, I am a newbie with longer skirts but I find it very difficult to walk with : the fabric keeps bunching in the middle and I spend most of my time adjusting it. Am I missing something ? Any advice on how to avoid it ?

    • Amber
      January 12, 2016

      I don’t normally wear petticoats, and I haven’t actually experienced what you’re describing, so I’m not really sure what to suggest – perhaps a slip of some kind would help?

      • Nini
        January 19, 2016

        I tought I had subscribed to the comments but apparently not, silly me !

        Yes, I will try with a slip under, see how it goes 🙂 I noticed it mostly with my coat on, I guess it’s just not full enough.

        Thanks !

  • Mika
    February 2, 2016

    I like the green coat as it is a beautiful coat on its own. However I disagree with the covering of the whole skirt length as it lends itself to the “Is she wearing anything underneath?” stares. Whereas the camel color coat prevents that and also gives a nice contrast (orange/blue) with the shes being neutral (black). Overall great post as you offer great styling ideas. Do you have any blogs for the longer midi skirts (and dresses)? What about non fuller midi skirts or midi pencil skirts?

  • Elena
    March 8, 2016

    Cool post! I like your modeling because you have a pleasant look on your face, unlike many “magical fashion unicorns”! That made me laugh. ? Thanks for providing the thoughtful info!