Styling dresses for Autumn/Winter ❄️

Hi Darlings, how cold is it right now ❄️?!Are you lost for inspiration now the weather has changed and you feel like you’re lost under all those layers? Well never fear, your girl is here to give you some inpiration when it comes to winter wardrobes. I am a huge lover of dresses and love to style these throughout the seasons. Don’t be put off during the Autumn and Winter, this is still a perfect time to make the most of styling your dresses.

Controversial, but I am just not a fan of the big cream chunky cable knit jumper dress, I don’t know why but they just aren’t for me. I am not one for separating my clothes into seasons either, I like to invest in pieces that can take me through any season, and can be styled in a multitude of ways. After all, who wants to stash away their favourite pieces for 6 months of the year… not me! I wanted to bring you some inspiration when it comes to all different types of dresses, even your print dresses, to show you that they don’t have to waste away in a box for the rest of the season now. I’m going to show you just how easy it is to keep your wardrobe favourites out all year round. Also, don’t forget, the winter also includes being inside, and we need something fabulous under those coats, scarves and winter woolies.

If your dresses are refusing to be packed away this year, this blog is for you. Let’s have a look just how easy styling is 👗.

Enjoy x


My Best Friends Wardrobe Paisley Dresses

First up, these two dresses from My Best Friends Wardrobe give me all the Autumn/Winter styling vibes. If you haven’t seen the dresses this brand have to offer, where have you been?! The quality and design of their dresses ooze elegance and they have been a firm favourite of mine when picking out an outfit. The ladies behind the brand are also super helpful and always happy to help if you have a specific need or something in mind.

These two dresses mentioned are quite similar, but in my opinion one is more every day dress, and one is more ‘party or evening’ dress. Let’s start with the ‘everyday’ dress.

This dress is absolutely stunning. The colours are perfect for Autumn/Winter, and the different colours within the dress actually make styling easier not harder, as you can pick out a specific colour to accessorise with, or pull through into your layers. The design of the dress is more of a smock style, meaning it is loose and easy to wear. It has a lower v to the front, meaning it would be more difficult to layer up underneath, but the movement of this dress means layering over the top is nice and easy, and you wont have restricted movement like it some dresses!

I chose to pair the dress with Chocolate Fairfax and Favor Regina Boots (linked here). These are my ‘go to’ winter boots girls. These are the flat version, and I find the chocolate suede is practical and durable in the Autumn/Winter months. Wearing longer boots means you can tuck cosy warm socks inside, and no one knows! If you’re styling a dress in winter, you do want to utilise hidden layers where ever you can – and after all, no one wants cold feet do they! Paired with a tan belt round the waist, this helps to nip the dress in, and keep things looking feminine.

I also paired this look with the Fairfax and Favor Elizabeth Gilet, which was released earlier in the year (linked here). The chocolate tones of the gilet compliment the whole look of the outfit, and a cosy Toscana Gilet is the perfect addition to your winter laying.

For the second dress, this is similar sorts of colours, but there is a subtle glitter thread that runs through the dress, making this the perfect party season dress. The dress is also redder in colour, making it absolutely perfect for this time of year! The dress nips in at the waist with an elasticated waistband, creating an ultra flattering fit, it also has a gorgeous high neck bow. The sleeves on this dress are full length. This dress is so easy to layer underneath. You could wear a top or thermal underneath the dress and the bow would hide this away, keeping you warm, but also looking ultra stylish.

I’ve paired this dress with a black velvet jacket, to create a classic, cosy winter look, perfect for your Christmas parties, meals out or evenings with friends. I’ve opted for ankle boots with a heel, but cosy fleece tight to keep me warm. You can pick up these types of tights from Primark for a few pounds. They are fleece lined. I will often wear them to the races if I want to wear a skirt – but I also wear them under trousers when it is really cold as an extra layer!

I’ve also styled this dress with a fur snood. This particular one is from Eton Taylor (linked here). This is the perfect accessory for pairing with dresses or skirts this winter to keep your outfits looking cosy and warm. Adding layers in the winter doesn’t have to be bulky, you can see keep it feminine and elegant looking.

Ultimately these dresses are fabulous for layering with with if you’re going to be outside, but also have the ability to be dressed up perfectly for your evening plans.

Shop the My Best Friends Wardrobe dresses here.


Teddy Edwards Lily Dress

If you follow me on Instagram, you’ll have seen how obsessed I am with the Teddy Edward Moleskin Jeans (linked here). Moleskin is such a great fabric for this time of year, it is warm, comfortable and stylish. When I saw the Lily Dress, I instantly fell in love. A unique take on the popular shirt dress, this gorgeous dress can be dressed up or down, depending on the look you are going for. I absolutely love this dress and was so excited to get styling with it.

The Lily dress comes in women’s sizes 6-16. It is designed for a tailored fit, and should fit above the knee. The moleskin has a slight stretch with achieves comfort as well as style. Nickel buttons finish off the look.

Styling a dress with a fedora is an easy way to dress it down and create a more casual every day look – also perfect for the wet weather and showers we see in our good old British weather! Don’t be afraid to try a fedora with a more dressy dress, I’ve used this technique all Summer at shows, and it really works! Paired with over the knee boots, you can easily create a look that will transition you from summer sunshine to autumnal evenings.

I’ve also paired this dress with tan over the knee boots, and some fur. Accessorising with fur/faux fur adds an instant autumn/winter feel to your outfit, and keeps it looking cosy and warm. You could layer up underneath the lily dress, or throw on an additional jacket and woolies to keep you warm until you head inside.

Don’t forget with your winter styling, that if you are laying up, but are ultimately going to be spending time inside, you will need layers that are easily removable when you warm up! If you are going to be stood outside all day, concentrate on thermals and under layers to trap heat!

The Lily dress from Teddy Edward has a timeless elegance about it, a subtle country take on a classic style, this dress is sure to carry you season to season, and inspire endless outfit ideas.

Shop the Lily Dress here.


Latham and Taylor v neck dress

The Latham and Taylor Whalley V Neck dress is a Mongolian cashmere dress, available in Oatmeal and Sand. This dress comes in S/M or M/L sizing.

This beautiful dress is an a timeless classic, perfect for dressing up or down. This style comes up as a looser fit on me and is more of an oversized look. Traditionally I wouldn’t go for anything too oversized, but this was the perfect amount, and gave it an elegant but cosy feel. With these sorts of dresses, you can nip them in at the waist with a belt. I opted for the Fairfax and Favor Sennowe Belt in Oxblood (linked here). This complimented the tan tones in the outfit perfect, but also the warmer tones add a subtle hint of Autumn/Winter.

I’ve paired this dress with a classic long line tweed jacket. Tweed jackets can instantly add a more Autumn/Winter feel to your outfits. This gorgeous tweed is from Welligogs (linked here), and styles amazingly well this time of year. I am absolutely someone that will wear tweed all year round, however, paired over a dress at this time of year helps to achieve the perfect autumn/winter styling you are desiring to achieve. The red and green tones in this tweed also add to the desired styling affect. This outfit is perfect for town or country, so you really aren’t limited.

The dress is a longer length so I’ve gone for a subtle pair of ankle boots. Tights in the same colour as the boot help to elongate the leg, particularly with a longer style dress and short boot. I think you’ll agree this outfit has achieved perfect autumn/winter elegance.

Cashmere is such a desirable clothing material, and these clothes are an investment that will last and last, carrying you through all the seasons, and remaining a firm favourite in your wardrobe, whatever the occasion.

Shop Latham and Taylor dresses here.


Missguided Animal Print Dresses

I picked up these Missguided dresses fairly recently as an impulse buy. They came up as a sponsored ad on one of my social media sites, and I immediately knew I could have some fun styling them. I also knew they could work for both Summer and Winter fashion. For me, I don’t put any of my clothes away for the change of season, I like everything to be fairly versatile.

First up is this gorgeous pink pattern dress. This reminds me of a porcelain print effect. The dress is long sleeved and has a tie up by the neck, although I actually left this undone for a different look.

I chose to style this dress with a Toscana gilet again. This is fast becoming my go to item when styling up my autumn/winter outfits. It pairs so beautifully over a dress, whilst ensuring warmth and practicality is still a priority here. I have again paired the look with ankle boots – these just don’t need to be packed away in the winter – continue to utilise them, just find a way to style them that works best for you. The fleece lined tights are again another way to ensure warmth when wearing a shorter boot.

The second dress I picked up for the same sport of pattern, but in a light blue. This dress was more of a shirt dress, than the one above. But also with long sleeves, meaning a really simple styling cheat!

Pairing this type of pattern with long boots and fur can distract from thinking it is a summer pattern. I personally think it works really well under layers, particularly a cosy fur. Using Navy accessories has helped to darken the whole outfit style, further creating a winter look instead of summer style.

I have loved styling both of these Missguided dresses. I rarely buy from high street style stores, however it is so easy to show with these dresses just how affordable country styling can be. These two dresses are fast becoming a couple of my favourites, and I have already been styling them in so many different ways!

Shop the Missguided dresses here.


Take Home Top Tips:

– Primark or similar stores offer fleece lined tights. These will be one of the best investments that you could make if you love styling dresses in the winter. I rely on these, particularly at the races, when I want to style a dress, without getting cold legs.

– Utilise your layers! Just because it’s a dress, don’t let that stop you layering. Gilets, coats and scarves all layer really well together. Alongside this, use thermals or tops underneath your dresses if they have a high neck, this will allow you to stay really cosy!

Boots! Tall boots are a great way to finish off styling your dress in Autumn/Winter. Whether knee high, or over the knee, a pair of boots will help to keep your lower leg warm and you can hide your toasty socks inside!

Fedora hats are perfect for protecting your hair and head from unexpected showers, or unpleasant winds.

Don’t be scared! It’s all too easy to pack away what we think is our ‘summer wardrobe’, but if you are investing in clothing, it often has the ability to carry you through all the seasons, and why would you want your favourite pieces to be hidden away – I certainly don’t.


I’ve loved putting together this little style guide for you! I wear dresses so much that I wanted you to see just how easy it is to still style them during the Autumn/Winter period.

I can’t wait to see how some of you chose to style your own dresses!

Until next time,

Lots of love, Lucinda, xo

‘It’s not about the dress you wear, but the life you lead in the dress’ – Diana Vreeland

{some dresses were supplied for this blog post. None of the links in this blog post are affiliate links}

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