10 Ways to Style Dresses in Winter

How to make dresses warmer is a common problem we all face when we style dresses in winter. It seems excessive to have a summer AND a winter wardrobe, without being able to transition any of our favourite pieces between the seasons, doesn’t it? But don’t worry, I’ve got you covered with my best styling tips for wearing your dresses in the colder months.

Here are some initial ideas to get you inspired before we dive into the 10 best ways to style dresses in winter, with picture examples styled by me.

How to style dresses in winter

1. Wear a cropped knitted sweater over your dress that cinches at the waist for a trendy and warm silhouette
2. Pair your dress with leggings or thermal tights
3. Wear a turtleneck or an extra layer under your dress
4. Pair a bodycon dress with a faux fur coat for a chic yet cosy outfit
5. Layer a chunky scarf over your dress to add stylish warmth

Now let’s get dressed…

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1. Pair your dress with leggings or thermal tights

Wearing your dress with cosy leggings, fleece-lined tights, thermal tights or even ‘temperature controlled’ tights, can be a great way to warm up your winter outfit, whilst still being able to wear your favourite year-round dresses.

The tights I’m wearing in the below picture are a set of ‘temperature controlled tights’ from Marks and Spencer’s here in the UK, that warm you up in winter and keep you cool in the warmer months – sounds like magic, right? They work wonders for keeping legs warm under dresses in winter, and feature as an essential piece of my winter wardrobe.

Get a similar pair of thermal tights on Amazon here:

Leggings will work just as well and are a great way of keeping your legs warm when wearing shorter dresses in the winter. Fleece-lined tights are a super snuggly option too!

Leggings or warm tights under your dress work great for keeping you warm in both indoors and outdoors during the winter months. If you are stepping out, just throw a coat on over your dress and your outfit is complete.

Wearing leggings with your dress whilst working in an office is a great way to warm up at work too.

In the below picture I styled one of my favourite summer dresses with a pair of temperature controlled tights, black boots and a plaid handbag. This summer dress was easy to style in winter, as the floral pattern features black as one of it’s colours, which I could match to the tights, boots and handbag. To finish off the look I added a super soft black fur coat for when stepping outdoors.

To make the above outfit even warmer, I would add a thermal vest underneath the dress, or I would pair it with a simple black cardigan.

If you like my boots shop a similar pair here:

2. Wear a turtleneck or an extra layer under your dress

Style dresses in winter by adding additional layers of clothing underneath, such as thermals, an extra t-shirt or camisole, or a turtleneck, for a warm yet stylish look.

A turtleneck looks great underneath a dress in winter, and is an easy way to transition your summer dresses into winter outfits.

The dress I’m styling in the above picture is a short, summery wrap dress, which I initially thought would be difficult to style for winter. However with a black turtleneck, warm tights, black boots and a monochrome bag, the dress looks great!

I could also have paired the dress with a white turtleneck, to match the polka dots on the dress.

Tip: take a look at the colours and patterns of your summer dresses and see if you could match any of the elements to a turtleneck, a cardigan or a shrug that you already have in your wardrobe.

Whilst we’re on the topic of warming up short dresses, let’s answer the following…

What to wear with short dresses in winter

1. Thick leggings underneath your short dress in winter instead of tights
2. Additional layers, such as a thermal camisole or vest, under your short dress in winter
3. Tall thigh-high or knee-high boots to warm up your legs when wearing short dresses in winter
4. A long coat to warm up your legs when wearing a short dress in winter
5. Layer another close-fitting dress under your short dress in winter, such as a bodycon dress or a slip

3. Wear a jumper over your dresses in winter

Layering a jumper over your dress in winter is a great way to warm up your outfit, whilst staying stylish. The best style of jumper to wear with a dress is a cropped, knitted jumper that cinches at the waist to maintain a flattering silhouette.

Adding a jumper over your dress is a cute and cosy way to stay warm when transitioning your wardrobe between the months. It’s easy to add a cropped jumper to a strappy bodycon dress that you might wear by itself in the summer, so you can wear the dress all year round. This way your tighter-fitting dresses will see use in the winter months!

I added a red cropped jumper with frilled cuffs, neckline and hem to my strappy black bodycon dress to cover up my shoulders and arms and create a classy style. I finished off the look with a red handbag to tie in the colours. This is an easy way to style a midi bodycon dress in the winter.

For a shorter bodycon dress you could simply add some warm tights to complete the look.

4. Add a slip or extra skirt under your dress for warmth

An easy way to make dresses warmer in winter is to add a skirt underneath for a hidden layer of extra warmth.

Pairing your dress with a hidden skirt is a quick way to warm up your legs, without compromising the look of the outfit. Have a look through your wardrobe and see what skirts you have that would fit underneath your dresses and experiment with hiding them under the fabric.

I find skater skirts of a jersey material work particularly well for this (as pictured above), as the material is thin enough for it not to bulk out your dress, and the waistband is closely-fitted, so it isn’t noticeable under the fabric.

This is a super easy way of warming up your lower half in winter, and works well with long and short dresses. Simply add a longer skirt under your midi and maxi dresses, for a hidden layer of warmth.

You could also add a full body slip if you have one, as this follows the same principle.

Finish the look with a jacket to cover your upper body. I paired a leather jacket with a velvet green dress, with a black skater skirt hidden underneath.

If you like my jacket, shop a similar one here:

5. Choose a sweater dress or a dress with sleeves in winter

A simple way to style dresses in winter is to opt for a sweater dress or a dress with longer sleeves, to keep your upper body warm. Pair your dress with thick tights and a jacket to finish the look.

Sleeved dresses are versatile pieces to keep in your wardrobes for transitioning between the fall and winter months. Add layers over them in winter, or a light jacket over them in autumn.

Sleeved dresses are also a great option for work/office wear in the winter months, as you can wear them alone, or with an indoor-appropriate jacket.

I have styled my sleeved orange dress with a tweed jacket, that can be layered underneath a coat, or worn as an indoor jacket in the office, for a stylish yet warm look.

If you like this tweed jacket (it’s one of my wardrobe staples, and really affordable too!), you can shop a similar one here:

6. Pair your dress with an indoor jacket or blazer when at work

Stay stylish and warm in the winter months by wearing an indoor jacket or a blazer when at the office.

Many office workers complain of chilly working conditions – we all know what it’s like to have a boss be stingy with the heating! Wear a blazer or an indoor appropriate jacket over your work-wear dress to keep your upper body warm without compromising your professional style.

I paired a shift dress with a tweed jacket in the below picture to show how a summer dress can be styled in winter with an office-appropriate jacket. The dress is sleeveless, which makes it difficult to wear alone in the office in the colder months, but styling it this way was perfect.

Add a thermal layer underneath and a professional blazer or jacket to transition your summer shift dresses into winter-ready office outfits.

Whilst we’re on the topic of summer dress, let’s look at…

How to wear summer dresses in winter

1. Add a slip or a thermal layer underneath your summer dress
2. Wear a blazer or an indoor appropriate jacket over your summer dress whilst at work
3. Pair your summer dress with tights of a colour that matches or compliments your dress

7. Wear a long coat and long style dresses in winter

Wear a long dress and a long coat in winter to stay warm without compromising style. Pair dresses and coats together of the same length and of colours that compliment one another.

When choosing a coat to pair with your long dress in winter, opt for a coat that is cut to the same length of your dress, to create a seamless look. If the layers are of different lengths the outfit won’t look as put-together. When picking out a long dress choose a material that isn’t bulky and will be easy to layer.

I layered a long lapel-collared coat over a black bodycon dress that I usually wear in the summer. For extra warmth add a turtleneck underneath the dress to cover the shoulders and arms, whilst creating a chic style. I find that turtlenecks always look classy and can elevate any outfit.

How to wear a midi dress in winter

1. Pair your midi dress with a coat of the same length, to maintain a seamless silhouette whilst staying warm
2. Wear tall boots underneath your midi dress to keep your calves warm
3. Add a slip or layer another dress underneath your midi dress for a hidden layer of warmth

8. Add a chunky scarf to style dresses in winter

Add an extra layer of warmth when you style dresses in winter by adding a chunky scarf. A large scarf will cover the shoulders and neck area, to trap your body heat whilst still looking stylish.

Scarves are an easy way to both warm up an outfit and elevate the style of an outfit with a cosy and classy touch.

I paired a chunky felt scarf with a fleece jacket, over a black bodycon dress, for a chic yet warm look. Finish off the outfit with a bright handbag, for a pop of colour.

Whilst we’re on the topic of trendy winter accessories, let’s answer…

How to wear dresses in winter 2021

1. Pair a bodycon dress with a faux fur coat for a chic yet cosy outfit
2. Wear a cropped knitted sweater over your dress that cinches at the waist for a trendy and warm silhouette
3. Layer a chunky scarf over your dress to add stylish warmth
4. Pair your dresses with trendy chunky boots in winter 2021

9. Wear a faux fur coat with your dress for stylish warmth

Style dresses in winter by pairing them with a long faux fur coat, for a timeless and elegant look that doesn’t compromise warmth.

Faux fur coats are a winter staple in the wardrobes of best dressed celebrities and influencers, and with good reason – they always look classy whilst keeping you really warm. Layer a faux fur coat over your dress in winter to elevate your outfit and stay cosy.

In the above picture I paired a floral dress with black detailing with a long black faux fur coat, as an easy way to transition a summer dress into a winter outfit. Add heeled boots for an extra touch of style.

Here are some more ideas…

How can I be warm and stylish in winter?

1. Wear a chic turtleneck underneath your dress for a classy layer of warmth
2. Pair your dress with a faux fur coat for a cosy and cute look
3. Style your dresses in winter with thigh-high boots over tights for a sexy yet warm look

10. Wear tall boots and thick socks over your tights to style dresses in winter

Wear thick socks underneath tall boots to keep your ankles and legs warm whilst you style dresses in winter.

In the above image I paired woollen grey socks with gold heeled boots for a stylish twist. I would recommended wearing even taller boots than those pictured above, with knee high socks over tights, to keep you extra cosy.

Shop a similar pair of boots here:

Thank you for reading this article on ‘How to Style Dresses in Winter’ – I hope you feel inspired to have a look through your wardrobe and start pairing items! For more style articles, check out the below…

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