There was a time (hello 2012-era me!) when you’d rarely find me in a skirt longer than mid-thigh. 

Denim minis, flared skater skirts, anything short and swishy — that was my entire wardrobe (we’re going to take a dive into the past with this post by the way!). 

A skirt that hit below the knee felt far too “grown up”, and the idea of wearing a midi dress was just not something I really ever considered.

But somewhere between leaving uni and figuring out what suits my shape best, midi dresses and midi skirts have become absolute staples in my winter wardrobe. I find the longer lengths balance my proportions, skim nicely over the old hips, and feel far more flattering and confident than anything too short. (Doesn’t mean I don’t still wear mini skirts though, maybe that’s a post for another day!)

There’s just one problem I’ve often come across:
How do you actually wear midi lengths in winter without freezing, looking boxy, or feeling like your legs have vanished?

After more trial and error than I’d like to admit, I’ve worked out some simple styling rules (and when to break them) that make wearing midis in cold weather feel effortless. 

I’ve been having fun finding my personal style again after getting a colour analysis by House of Colour last year. This season, I’ve really dived into what I’m calling my “Practical Magic era” – swishy skirts, 90s/00s inspired witchy vibes, quirky details and all that. I’m also trying to buy secondhand wherever feasibly possible, so mostly charity shops and Vinted. More on this another day, but after seeing that there are enough clothes on the earth to clothe the next 6 generations, I’ve decided that I should try to get through some of those – a bit like ticking off books on your shelf!

So it’s time to dive back into the past, as well as showcasing some new outfits I’ve put together recently and loved. Whether you love full skirts, fitted knits, pleats, wrap dresses or casual midi daywear, here are the winter outfit tricks that I’ve been using to get my style back on track in the colder months.

How I Style Midi Dresses & Skirts in Winter

Okay, so I’ve tried to be like the cool girls on Instagram and I’ve filmed an outfit video (or two or three, keep an eye on my socials for more!). I have no idea why I thought it was a good idea for me to get out the treadmill and do that, but here we are. And I haven’t broken my ankle doing so – I think that’s a win!

This is a little peek into my current wardrobe – how I’m wearing midi skirts and midi dresses in autumn and winter time of year along with the right accessories to try and keep warm!

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What Top To Wear With A Midi Skirt

My favourite tops to wear a midi skirt in autumn and winter are:

• Mesh top – this adds an extra layer of warmth over a vest top as well as visual interest.
• Bodysuit – a bodysuit helps with a smooth line under your skirt.
• Turtleneck fitted top – with full midi skirt
• Oversized jumper – tucked in to a fitted midi skirt

Top Tips for Wearing Midi Dresses and Midi Skirts in Winter

These are my tried-and-tested ways to create warm, flattering outfits that look polished, without bulky layers or awkward proportions.

1. Choose the Right Tights

Tights can make or break a winter midi outfit. They’re not only an opportunity to keep warm, but also give you the chance to have some fun with your clothes in the winter weather.

Nude tights

Tights that match your skintone create the illusion of bare legs but still add a little warmth. They work beautifully with both dresses and skirts. The only caveat is to make sure you get good quality ones, as I’ve definitely suffered at the hands of baggy tights bunching around my ankles before!

Opaque tights in softer shades

If nude feels a bit chilly or just looks a little bit off (especially if it’s snowing!), try:

• grey
• charcoal
• chocolate brown
• soft navy

They keep you warm without cutting the silhouette in half.

Black Tights

So a lot of people don’t like to wear a pair of black tights under longer skirts as they think it creates a harsh dark line that shortens the leg. I’ll be honest, I don’t live by that rule – as you can probably see from my video above! I wear black tights 90% of the time, sometimes a solid opaque black (which is probably a huge style no-no!), sometimes a more sheer black pair of tights.

Colourful Tights

Back in the day, I used to wear every possible shade or colour of tights under the sun. In fact, I once wrote a post about all my different coloured tights (which desperately needs updating!). 

Last weekend, I decided I’d give that old way of styling my outfits another chance – and here’s what I’m wearing today: a pair of bright fuchsia tights with a colourful midi skirt! This also fits the brief for a jewel winter outfit too, so I feel like I’m ticking all the boxes.

Wearing a pair of colourful tights that coordinates with your outfit gives you a chance to rewear and remix items of your wardrobe with lots of different looks – remember back in the day when remixing an item of clothing was all the rage?! I’m planning to bring that back!

Thermal leggings under longer styles

For windy days or very cold weather, thermal leggings with a midi length dress or skirt are a game changer. Nobody sees them, but you get that extra layer of warmth that even a pair of thick tights can’t give.

2. Balance Full Skirts With Fitted Tops

If you’re wearing a full, pleated, or A-line midi skirt, pair it with:

• fitted jumpers
• long sleeves
• bodysuits
• ribbed tops

It creates the most flattering silhouette and stops your shape from getting lost under bulky winter layers.

The same works in reverse: if your skirt or dress is fitted, you can go slightly looser on top with a knit or chunky cardigan.

3. Get Strategic With Coats and Jackets

This was my biggest winter struggle for years. The wrong coat can make midi lengths feel frumpy, especially if it hits just above the hemline of your midi skirt – argh! Here’s what actually works:

Cropped coats and jackets

A cropped cardigan, leather jacket, denim jacket or fuzzy jacket keeps your waist visible and avoids the “boxy” effect.

The longer coat (my favourite)

A long coat, wrap coat or belted wool coat that reaches your knee or below creates a long, sleek line. No awkward hem clashes. No random proportions. Just warm, elegant winter outfits.

If you’re buying one coat to wear with midi lengths, make it long to cover all bases!

4. Pick the right boot

Footwear can completely change how a midi dress or skirt looks. 

Knee-high boots

These are perfect for cold weather and the easiest way to create a seamless leg line. They look super chic under:

• A-line midi skirts
• pleated skirts
• sweater dresses
• ribbed knit dresses

Over the Knee Boots

This is something of a new one to me! I used to have a pair of thigh high boots back in 2016, but I got rid of them a few years ago as they just didn’t get enough wear and were taking up too much room (they’re so big!). 

After seeing influencers wearing thigh high boots again, but this time under midi skirts and dresses, I thought I’d better give it a go. 

Game-changer!

You get the same sleek line that knee-high boots give, but with added warmth too! 

Mine are heeled, black ones, but not too high – I’m slowly learning my lesson on that!

Ankle boots

I’ve always found ankle boots with midi lengths quite tricky. They sometimes create an awkward line across your leg.

They’re still a great option, especially with casual midi dresses, as long as the boot sits close to the ankle to avoid shortening the leg. They’re also good with maxi dresses in the winter too.

Heeled boots

A mid or block heel adds length back if your dress cuts mid-calf. Great for work or formal occasions.

Knee-high socks under boots

This is just a hidden little trick for extra warmth, add extra socks under your boots on top of your tights!

5. Don’t Fear Layering (Just Make It Intentional)

Winter outfits often need more layers, but you can avoid bulky looks by choosing them thoughtfully.

Longline cardigans

Perfect for soft, relaxed outfits with casual midi dresses. Just watch that the hemlines align nicely!

Cropped Cardigans

A cropped cardigan is sometimes considered a style fail with a midi skirt or dress since it chops that long silhouette in half. But honestly, I’ve always been a fan of this look! It nips you in at your narrowest point. I feel it gives more of a retro vibe, which is kind of my thing anyway, so I’m okay with it.

Vests

This is my new thing, if you haven’t already figured out from my video – a denim vest or waistcoat with a midi length just looks so perfect to me! Not only have you got an extra layer for warmth, it also adds visual interest to your winter wear. It’s a great way to show your style personality a little bit.

Same with a corset – I LOVE adding a corset to a midi dress! It’s just not all that easy to wear in day to day life, but, you know, I’ll suffer!

Sweater dresses count as midis too

A ribbed or knitted dress is an effortless winter outfit. Add ankle boots or tall boots and a warm coat, and you’re done without having to overthink accessories (which I’m terrible at remembering about!).

Belts are your best friend

A slim (or chunky) belt can add instant shape under an oversized layer without adding bulk. I also like adding a dainty belt for a whimsical touch.

6. Accessorise Smartly in Cold Weather

Accessories make a huge difference to your winter midi looks (even if I forget about them all the time):

• belts to define the waist
• scarves in complementary tones
• berets or knit headbands
• a structured bag to contrast softer silhouettes
• minimal jewellery for formal events

A balanced outfit always looks that little bit more polished. I learned about the 7-point rule of style at my House of Colour analysis which says that every component of your outfit counts for one point, and 7 is the ideal number. I try to do it when I can!

7. Break the “Rules” Whenever You Want

Everything above is what I personally find most flattering or comfortable, but I still break my own rules all the time! 

Most days you’ll see me:

• in black tights with a winter midi dress
• wearing flats with an A-line skirt (literally right now)
• pairing a hip-length cardigan with a fitted midi
• choosing comfort over proportions
• a casual midi dress with smart shoes (why not?!)

Your personal style matters more than any styling trick.

Midis are meant to be fun, expressive and comfortable. If you feel good, that’s the only rule that counts.

How to Wear Midi Skirts and Midi Dresses for a Special Occasion

Back in the day (how old do I sound right now?!), we used to exclusively wear mini skirts and dresses to go out on the town – literally, the shorter the better. And tighter too. Remember bandage skirts?!

Nowadays, it’s going back the other direction. For special occasions, midi skirts and midi dresses just feel that bit more sophisticated and put together. For example, I wore a gorgeous tulle ballet inspired midi skirt for my work Christmas party one year:

Styling Midi Skirts in Winter: Your Extra Guide

While midi dresses get most of the attention, midi skirts deserve their own section because they’re incredibly versatile and easy to adapt throughout the winter season.

Choose a skirt with structure

Winter-friendly fabrics keep their shape and hold up in windy weather:

• wool blends
• pleated chiffon with lining
• corduroy
• thicker rib knit
• structured A-line silhouettes

These pair well with boots and winter coats without clinging or flying everywhere.

Use the half-tuck trick

A jumper or long sleeve top half-tucked into a midi skirt gives instant shape and stops the skirt looking overwhelming.

Experiment with oversized knits

A cropped chunky cardigan or boxy jumper works beautifully if the skirt is fitted. Use the “bra tuck” shortcut if you want faux cropping without committing to a cropped knit.

Shop My Favourite Winter Midi Outfit Pieces

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FAQs About Wearing Midi Dresses in Winter

Are midi dresses warm enough for winter?

Yes, with opaque tights, a longer coat and tall boots, they’re much warmer than short skirts!

Are midi skirts flattering?

Midi lengths balance out proportions beautifully on different body types, especially when styled with fitted tops or structured knits.

What shoes go best with midi dresses in winter?

Knee-high boots for warmth, ankle boots for casual days, heels for formal occasions. I also wear ballet flats with midi skirts and dresses often too.

What coats work best with midi skirts?
Long coats, leather jackets, cropped cardigans and wrap coats all work depending on the look.

Once you figure out your ideal proportions, whether that’s knee boots and a long coat, or a fitted top and pleated skirt, midi dresses and skirts are one of the easiest and chicest ways to dress for cold weather. I love the versatility of being able to take a summer midi dress and making it work for winter.

They’re versatile, cosy, flattering on different body types, and perfect for various occasions from workdays to winter evenings.

If you want to see more styling ideas (and more winter midi looks!), make sure you’re following along on Instagram, TikTok and YouTube Shorts. I’m going to try and post new outfits there as often as I can!