Styling Full Skirts in Cold Weather

Winter Midi 11

This isn’t really a post I expected to write at this time of year. My head was full of outfits featuring pastels and peep toes by now, but sadly the weather is not cooperating. Bearing in mind a large chunk of my wardrobe is made up of retro styles – specifically full, midi length skirts and dresses – this has posed a bit of a challenge. I don’t think from looking through the last few months of outfit posts you would even know what a passion I have for 50’s style shapes as they just aren’t all that easy to wear in the cold. I have my ways though, so since it doesn’t look as though I’ll be ditching the tights just yet, I thought I’d fill you in on how I manage to wear my prettier frocks without freezing (when there isn’t a few inches of snow on the ground, at least…)


The beauty of the 50’s silhouette is of course the nipped in waist, so you don’t want to add too much bulk around the middle. Still, it isn’t impossible to maintain this shape with some added warmth – try layering a cropped cardigan or sweater on top, or in absence of one of those, knitwear can be tucked in to a skirt – just go with something in a fine knit and not too bulky.


This is where things have always gotten difficult for me, because I despise tights and really feel like these styles look better without, however I’m too old and wose now to attempt foregoing them in the name of fashion! So I have a few selected options for combatting this without feeling like I’ve ruined the look entirely…

Over The Knee Boots

Many a time have I waxed lyrical about my love for my Dune ‘Stretchy’ boots, they were a pricey buy, but well worth it as they are a lifesaver when temperatures plummet thanks to their slimline shape which means they can be worn under both full skirts and pencil skirts without creating lumps and bumps. Back then, the style was quite tricky to come by, which slouchier shapes being the look of the time, but this year the shops have been full of ‘sock’ boots, and I highly recommend you invest in a pair! I love how they keep you warm all the way up (oo-er) but since you can’t see the tops they still look conservative (I personally have no issue with showing the tops of my OTK boots, BTW, but it’s a look I reserve for weekends rather than the office) The resulting look is beautifully streamlines and doesn’t alter your proportions like calf or knee high boots might do.

Winter Midi 1Winter Midi 2

‘Hepburn’ Dress, The Pretty Dress Company (other colourways available) – ‘Stretchy’ Boots, Dune (Similar)

Ankle Boots

Now, this one may be contentious, as plenty of people have a strict rule against wearing ankle boots with midi length skirts due to the potential to ‘chop up’ your legs. This can be true, particularly if you go with a flatter or chunkier boot which can make the whole look a little frumpy. I find if you stick with a high and slender heel you should be fine. Most of the time I will match the colour to my tights to replicate the above streamlined effect, however in this example I’ve picked out a colour from the pattern in the dress which can also work quite nicely. Incidentally, I used to have a real issue with wearing anything other than black footwear with black tights for no real reason at all – I’m glad I managed to overcome the aversion as it can get pretty boring wearing the same shoes day in day out!!

Winter Midi 4Winter Midi 5

‘Vivi’ Dress, Lindy Bop  – Ankle Boots, Primark (Similar)


Similar to the above, I used to have a real problem wearing tights with shoes of any description! It’s all entirely in my head I’m sure, but I used to get completely irrationally bothered by and wrinkles around the toes or bobbles around the ankles – things that literally only I could see! I have found the best way to combat this is go with something that fastens around the foot – laces, straps or ribbon ties, anything really that adds a little coverage. Mary Jane’s have therefore become my favourite style during the colder months. The same principle works with flats – I’ll admit, I wear flats far less with midi’s as it can make me feel a little drab, especially with tights as well, but when it’s all a bit slippery and icy outside I’m not really willing to break a leg getting to work, so needs must!

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‘Peggy’ Skirt, Lindy Bop (other colourways available)

‘Aurora’ Shoes, Kurt Geiger (Similar) – Red Lace Up Flats, Zara (Similar)


What to wear on top of my outfit has always been the biggest challenge for me. Until my mid twenties, outwear was always a bit of an afterthought to me – one of those things you bought out of necessity rather than pleasure, and I was always more allured to a beautiful dress or an amazing pair of shoes when it came to spending my hard earned cash. Perhaps it was the fact that as I got older I started spending far more time at Gin Festivals and Farmer’s Markets than in pubs and clubs that made me realise investing in some great coats was more than worth it, as they are just as much a part of the ensemble as everything else! These days I have a far bigger selection to choose from, but these are the shapes that I find suit this style the best:

A long, belted style

Obviously, replicating the shape of the dress or skirt, with a nipped in waist, is always going to be a winner, but the key is in the length of the hem. Ideally you want it to be the same length or longer than the hem of the dress or skirt for a clean look. I am yet to invest in a really good Winter coat in this style, which is why it’s been a while since I wore a full skirt – it’s just been too cold! But I do have this lovely green trench from Collectif which is just perfect. It’s still a little chilly for a trench at the moment, but this one is actually padded and a little snugglier, so will be making an appearance any time now!

Winter Midi 3

Trench Coat, Collectif (Similar

A cropped jacket

Much like the knitwear situation, a cropped shape which cuts you at the same point as the waistband on your dress and skirt will complement the look perfectly. Anything that hits you lower – say at the hips – will lose that lovely hourglass shape you’ve strived so hard for! Smart jackets can be tough to find in this shape these days, but you can almost always find a good leather jacket which will do the trick nicely. As my style tends to be a nod to retro rather than full on repro, I like that it gives a slightly more modern twist to the look, and you can always layer up with a thick, blanket scarf for added warmth!

Winter Midi 10

‘Peggy’ Skirt, Lindy Bop (other colourways available) – Black Ankle Boots, Primark (Similar) – Leather Jacket, Oasis (Similar)

How about you – any tips I’ve missed, Vintage fans?



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