How to Wear Dresses in Winter

Disclosure: This post on how to wear dresses in winter contains Amazon affiliate links

If you’ve come here after typing some variation of the phrase “how to wear dresses in the winter” into either Google or Pinterest, I’m just going to begin this post by reassuring you that it’s OK: I’m not suggesting you wear this EXACT outfit in the winter. Calm down. 

No, this outfit is very obviously retro-inspired, and, to be totally honest, it’s not something even I would wear these days (I originally wrote this post in 2013, at the height of my pin-up style obsession, but I’m updating it in 2024, when my winter style mostly revolves around leggings and puffer coats, so this look is a little bit ‘extra’, even for me…)

But the principles are the same, though. Regardless of the dress itself, or your own personal style, there are some basic techniques that will allow you to wear dresses in the winter without freezing. Here are a few of them…

How to Wear Dresses in Winter

1. Pick the right dress to start with 

Again, I’m not talking about personal style here, because it’s a given that you’ll pick a dress you actually want to wear, not one some random redhead on the internet told you about. But you all those advice posts you see about how to wear a summer dress in winter, or whatever? Guys, this is not one of those posts. In fact, I’ll even go so far as to say you’ll never see me write one of those posts, because my philosophy on this is simple: DON’T DO THAT. Don’t try to wear a summer dress in winter. Don’t tell yourself you can just ‘layer it up’ with boots and tights and it’ll look fine, because, honestly? It won’t? It will look like a summer dress being worn with boots and tights: and summer dresses aren’t designed to be worn with boots and dresses, so unless you’re the kind of magical fashion unicorn who can just throw on anything and look amazing (And if you are, then I’m going to guess you don’t need to read this article, do you?), it’s going to be really difficult to make that look work. So choose dresses designed for the weather. Thick fabrics. Long sleeves. No weird cut-outs at the waist or shoulders. And then move on to step 2….

2.  Add tights (or leggings)

Boots and tights might not make a summer dress look wintry, but they will make a winter dress much warmer, which means it’s just a question of figuring out WHICH boots and tights to go for. Personally, I can’t stand ANY kind of tights: no, not even those ones you’re about to suggest that never fall down or make you feel like your legs are in some kind of horrible lycra jail. I hate all of them, so, instead, I’ll normally wear leggings, which look exactly LIKE tights once you’ve added your trusty pair of boots to them, but which I find much warmer, and more comfortable – especially the fleece-lined or thermal variety. Obviously this preference is purely a ‘me’ thing, so you do you, and wear tights if you want to; just make sure your legs are adequately protected from the cold, is all I’m saying. 

3. Add boots 

Next up: boots. My preference here has always been for over-the-knee boots, which are one of those items which look like they might be difficult to wear (Let’s just say that if you’re going to try it, you should probably brace yourself for all of the ‘Pretty Woman’ comments you’re going to get…), but which can be surprisingly versatile when you know how to style them. I like wearing them with dresses which are midi or knee length because the boots disappear under the hemline, creating a much smoother silhouette than you’d get with ankle boots, say, or any other footwear that basically draws a line across your leg at some point. With that said, ankle boots would also work with an outfit like this one: all you have to do is make sure your boots are same colour as your tights if you want to lengthen (or at least not shorten) the appearance of the leg. 

3. Petticoats / slips / whatever you want to call them

These days, petticoats and slips (we used to call them ‘underskirts’ when I was young, but I’m from Scotland, and we talk funny here, so take that with a pinch of salt…) are something a lot of us associate with a bygone age, much like Elizabethan ruffs and 19th century bustles. Actually, though, slips are still around today, and if you’ve never worn one, you’re missing out, because, as well as making your clothes fall more smoothly, and preventing your skirt from sticking to your tights due to static, slips will also help keep you warmer if you’re wearing a dress in the winter. 

As you can see, I’m wearing a tulle petticoat with this dress, which makes the look spectacularly “extra” and not at all practical for modern life. (Seriously, what was I THINKING?) For most of the dresses you might wear today, though, I’d actually recommend a simple silk slip, which won’t add any volume, but which will add warmth. (And some are really quite pretty, too, so you get to feel like you’re wearing something a little bit special…)

4. Other layers

In point number one, I mentioned choosing a dress with long sleeves. Well, as you can see, Past Me didn’t take her own advice on that, and the dress in the photos has three-quarter length sleeves, which I’ve cunningly made more wearable in winter with the addition of elbow length gloves. These would be of no use to me at all when I was inside, obviously, but when you’re outdoors, make the most of the gloves, scarves and hats at your disposal, kids – this is their time to shine. 

Oh, and one last “tip”…

 

Wear a freaking coat. 

I took my coat off purely to take these photos, but, rest assured, it was just out of sight, waiting to put back on as soon as we were done – there’s absolutely no way I’d spend more than a minute or two in the snow without one!