How to wear a midi skirt: a guide…

How to wear a midi skirtMidi 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 problematic, 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 shoesHow to wear a midi skirt: choosing your skirt 

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 these photos (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 skirtMy first two tips, then, are these:

01.  It’s all about proportion:

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?

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?

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

what top to wear with a midi skirt

How to wear a midi skirt: choosing a top

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?

what NOT to wear with a midi skirtI didn’t think so.

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:

midi pencil skirt and slouch sweater
Even then, I’d still want to tuck it, to create the illusion of a waist:

stripe top with tuckThis still isn’t a great look on me, which is why you don’t see me wearing slouchy sweaters all that often, but still, you get the point: volume on the top = no volume on the bottom. 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:

what shoes to wear with a midi skirtBy 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… (Now there’s a sentence I never thought I’d type…)

How to wear 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…

How to wear a midi skirt with boots

When it comes to boots…

what boots to wear with a midi skirtAnkle 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:

midi skirt and tightsIt’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 coat to wear with a midi skirtHow to wear a midi skirt in winter

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:

what coat to wear with a midi skirt?

biker-jacket-and-midi-skirt

How to Wear a Midi Skirt

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 - and how not to wear one

How to wear a midi skirt
56 Comments
  1. 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 🙂

  2. 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!

    1. 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!)

  3. 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.

    1. 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!)

  4. 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. 🙂

  5. 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!

    1. 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!

  6. 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).

      1. 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.

  7. 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!

  8. 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?)

  9. 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

  10. 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.

  11. 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!

  12. 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?

    1. 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!

  13. 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 ?

    1. 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?

      1. 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 !

  14. 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?

  15. 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!

  16. Sorry, but most of this advice is just wrong. Tucking a tight top into the waist of a flared midi looks absolutely old fashioned, very 50’s. The pumps only make it look worse. And those tall boots are awful with that skirt. Those tall boots are just awful, period. If you want to wear tall boots with midis you need to have a little more bulk at the ankle, rounded toe, and block heel, not those form-fitting pointed toe things. Ankle boots look fantastic with midis and they also look very current, but like the tall boots the ankle boots need to have some heft, a rounded toe and block heel. And no “shooties”! As for tops, tight tops look horribly old fashioned. If you want to tuck, wear a looser fitting tee or shirt/blouse. If you don’t want to tuck, wear a cropped or slightly longer loose fitting tee or sweater. You really don’t want to look like you stepped out of the pages of a 1950’s magazine ad for stoves!

  17. Amber,
    I like the advice you give about how to wear a midi skirt. It is spot on. While fashion is very personal, a close-fitting top with a midi skirt gives an optimal profile especially for us shorter women, because we don’t want to compromise the look by looking like we’re drowning in fabric.

  18. Hey Amber, really love your post and it couldn’t have come at a better time. I have this full midi skirt and I am wondering if I could pair it with sneakers but I am worried about that it’ll make my legs look short. I have to wear it to a dinner party, casual that is.
    Help

  19. I could swear I am following all the rules, but still get unfavorable reviews whenever I wear my “midi” (just below knee, as advised on here). I’m starting to think it’s a cultural thing because, living in Brazil, the Audrey Hepburn look isn’t quite as valued as the Kim Kardashian look…

  20. Finally some good advice about midi skirts! I love mine but never know what jacket to wear it with, thank you!!
    Can I ask where the long greenish coat is from? Its beautiful

  21. Thank you for this, it’s so useful to see the midi skirts paired with different shoes and jackets! I was wondering if you happened to have any tips about wearing palazzo pants, for a future post? I think I’m at the opposite end of the height scale to you at almost six foot tall, but I have two fabulous pairs of palazzo pants and I struggle with the shoes and jacket for them!
    Lisa | http://www.whatlisadidnext.com

  22. You addressed every single concern I have with midi skirts! Finally…someone who gets me! However midi skirts still look absolutely terrible on me. They are my favorite thing in the world but I think it’s just not meant to be 😢💔

  23. You look super cute but my problem is that I have a bit of a pudge to contend with and tucking is not a good idea so any tip on that! I love midi but usually wear a nice shirt but most definitely no tuck! Loved your article BTW. Hope to read more!

  24. I love this article. I am also 5’4 and for some reason it never occurred to me to get the midi dresses/skirts hemmed. I have now done that with all of my skirts to where they hit below my knee and it makes a world of difference, I have legs again! Thank you.

  25. I have just been looking at said magical unicorn girls on Pinterest for A/W fashion trends and I’m soooo glad I came across your article! It’s so great to see a trend converted in to common sense for normal people ( being more of a muggle fashion donkey than a magical unicorn…). I might actually attempt to buy one now and look nice not ridiculous. Loving your site. Will be back.

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