How To Wear Midi Dresses In Winter

How to wear midi dresses in winter
In the past I used to wear super short skirts all the time. Okay, they weren’t necessarily super short and it wasn’t all the time, but a few years ago, barely a week would pass without seeing me in my old denim mini skirt or flared black skirt that skimmed my thighs (nice face there, Sian :/). A skirt that hit at or below the knees was definitely not a thing of style to me, aside from the occasional maxi dress for holidays. However, in recent years, especially since leaving uni, I’ve noticed my skirts getting longer and longer, and it’s now rare to see me in a dress or skirt that sits too far above the knees. I’ve got rid of pretty much all of my old pieces that skim the thighs and feel far more comfortable in something a bit longer. It’s not necessarily that I’ve become more “modest”, I’ve just discovered that nowadays, longer lengths flatter my figure a bit more and balance me out, and who doesn’t love a figure flattering look?!
There’s only been one issue for me though, how are you supposed to wear midi lengths in winter?! I’ve seen plenty of uber cool bloggers and models rocking all sorts of looks with midi skirts, but not all of these are necessarily for me – some of them are wearing ankle boots (tends to make my legs look a little bit odd if the skirt is below the knee); some wearing over the knee boots (on me, where have my legs gone?!). The whole coat scenario is a different matter altogether – if your coat is just slightly longer than the dress or skirt, it looks a bit weird; if it’s too short you get cold. If you wear black tights, your legs look funny again, but nude tights are usually not as thick. Ah, the trials and tribulations of dressing oneself!
I decided to take a look back through my archives at ways that I have managed to pull off the midi skirt in winter, but obviously these aren’t absolute and are what have worked for me personally, so here are a few tips. I know that my dresses and skirts don’t all technically qualify as a true “midi” length, which is mid-calf, but this is what I think of as midi:

1. Go for nude tights

How to wear midi dresses in winter
I don’t know what it is, but for me, a pair of black tights looks a bit strange when you can only see the bottom half of my legs – I think it makes them look shorter or too “busy”, am I making sense?! Nude tights give the illusion on not wearing any, but your legs are still kind of (I repeat, kind of) warm. This can confuse people if you’re wearing them in the snow though; I speak from experience.

2. If you’re still stuck with tights, go for a paler shade

How to wear midi dresses in winter
If you find nude tights to be too thin, pale or chilly, one way I’ve figured out around this is to wear a paler shade of opaque tights, such as the grey ones from M&S above or these from Amazon which are available in about a bazillion colours (and I want them all!). By the way, this tartan midi skirt is my favourite AW purchase this year!

3. With a full midi skirt, go for a fitted, long sleeved or cropped top

How to wear midi dresses in winter
If the bottom half is full, go for fitted on the top and vice versa – that’s always been my rule for dressing myself in a more flattering way for my shape. It applies here especially since most of your legs are disappearing under the skirt, so you need to show there is a shape under there somewhere! The ASOS long sleeved bardot tops are my favourite way of creating this look at the moment, since I always need long sleeves!

4. Wear a cropped cardigan, jacket or coat

How to wear midi dresses in winter
If your cover up of choice (whether that’s a cardigan, jacket or coat) stops at your hips and doesn’t crop in at the waist, you’ll end up looking a little bit like a box unfortunately. While there’s nothing wrong with that, it’s not the way forward for the look I’m going for when I wear midi dresses, which is usually proportionate and ladylike.

5. Get a longer coat

How to wear midi dresses in winter
This may not be an option if you don’t often wear midi lengths, since it would be an expensive purchase to make, but I bought this fur collared and cuffed coat from Miss Selfridge this year and I haven’t looked back since. It is over the top, yes, but that’s never stopped me before, and I’m wearing it pretty much every day for work at the moment. I know it’s not technically “midi” length, and it has risen up a lot in this picture – it actually sits on my knees! A longer coat looks super sophisticated and grown up too (I promise, I am a grown up, really!).

6. Use heels to your advantage

How to wear midi dresses in winter
It’s pretty well known that wearing heels will lengthen your legs, and since midi skirts tend to chop off a big chunk of them, it’s only common sense to use heels to bring them back! I go for mid heels usually with midi lengths, only since I’m no good in massive heels. My latest purchase for this look is my Dorothy Perkins grey block heels – they’re really comfortable and just the right height for work and evening.

7. Ignore the rulebook

How to wear midi dresses in winter
Who decided these rules anyway? Oh yeah, that was me, above. And as you can see, they’re not exactly rules, and I don’t even stick to them anyway. Half the time you’ll find me in flats and midis, today I’m wearing a hip length cardigan with a fitted midi dress, above I’m wearing black tights, a fitted top and bottom, and flats – basically, I threw out all the rules and it didn’t look half bad, just goes to show really!


  1. November 17, 2014 / 9:24 pm

    I loved this post! I have very similar thoughts to you on styling midis (as well as problems, you couldn’t have phrased them better) I love all the outfits in this post (but pleeeeease you must stop making me want that tartan midi! :D) xxx

  2. November 17, 2014 / 9:41 pm

    you look so lovely in all these outfits! xx

  3. November 18, 2014 / 11:20 am

    I have similar issues with styling midis in winter, and also swear by the nude tights – I know a lot of people seem to hate them, but black tights DO make my legs look weird (or make the skirt/dress just blend into my shoes and tights, so the lower half of my body is just one black blob!) and coloured tights make me look about five, so nude it is! People do react quite strangely, though, and constantly tell me I “must be freezing” – I actually don’t find them much different from opaques in terms of warmth, though, so I just put up with the comments 🙂

    P.S. Loving the new layout, by the way!

  4. Jen
    October 12, 2019 / 2:16 pm

    Where did you get the red cropped jacket??

    • Sian Thomas
      October 14, 2019 / 8:16 am

      I believe it was from a brand called Sirens in Canada – it was probably about 7 or 8 years now I’m afraid, not much help, sorry!

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