Your guide to choosing a versatile winter dress and how to style it best

by Сашка

Thinking about investing in a new dress? Living in the UK means it’s worth considering how well it will serve you when the seasons change.

Even at the peak of summer, your best dress might need to be cold weather-ready at the drop of a hat.

So we're on a mission to help you find the perfect frock to see you through the year, despite what Mother Nature has in store.

With just a few smart style hacks, you can nail your outfit any time of year.

Unsure of the way forward? Fear not.

We're covering how to find a great warm-weather dress that seamlessly lends itself to winter weather. To fill out the vision, we've got some of our favourite pieces to fill out your wardrobe, too.

Best Buys' favourite versatile dresses

Invest in midi and maxi designs

Warm-weather dresses in midi and maxi lengths make for versatile and reliable wardrobe staples. They’re lightweight during the warmer seasons but can be worn with tights or even leggings underneath for a little extra comfort and warmth during the winter months.


Your guide to choosing a versatile winter dress and how to style it best

Photo: River Island

River Island Knit Cut Out Bodycon Midi Dress

You save £20 (44.44%)£45

A black dress is a classic piece that will work well no matter the season. We love the attention to detail on this River Island bodycon one; it has a cut-out detail on the chest, a kit ribbed design and two small side splits at the hem. Wear it to brunch at the weekend, that glitzy party, your next friends’ get-together or whatever life throws at you. The versatility of this black midi dress knows no bounds.

Transition it to winter: Wear with black or nude tights and ankle boots.

Your guide to choosing a versatile winter dress and how to style it best

Photo: Mango

Mango Knitted Turtleneck Dress

Chic and figure-hugging, the length of this Mango knitted jumper dress makes it an elegant winter dress ideal for cooler weather. Its sleeves and roll neck should keep you cosy.

Transition it to winter: Pop leggings on underneath to feel extra toasty.

Buy a dress that works well with tights

One of the easiest ways to transform a dress into a warmer outfit is by incorporating a pair of tights into your look. Opaque black tights work best with darker, richer hued dresses while funkier, statement tights will suit block-colour dresses.

Your guide to choosing a versatile winter dress and how to style it best

Photo: ASOS

In The Style Plus Button Through Mini Smock Dress

You save £14 (40%)£35

When it comes to plus-size winter dresses, we like this pretty blue smock-style piece. It comes with slightly puffed sleeves, a gingham design and a button-through front that sets it apart from other basic smocks.

Transition it to winter: Pair this dress with sheer black tights and a pair of ankle boots.

Buy a winter dress to wear with boots

Boots (no matter the style) are the staple of any winter wardrobe. Mini dresses are one of the easiest pieces to wear with a pair of boots. And of course, a mini dress is perfect when worn with sandals during the sunshine, too.

Your guide to choosing a versatile winter dress and how to style it best

Photo: New Look

New Look Black Leaf Print 3/4 Sleeve Belted Mini Dress

With puff sleeves and a belted waist, this flattering dress is perfect for warm and cool temperatures, as well as day-to-night looks.

We love how its leaf print pattern is eye-catching yet neutral.

Transition it to winter: Match with your favourite pair of boots (ankle and knee-high boots work equally well) and some thick tights.

Pick up a long sleeve winter dress

British weather isn’t exactly the most reliable — one minute the weather’s warm and sunny, the next it’s raining cats and dogs. So buying a dress that comes with sleeves is a safe bet for chillier spring evenings as well as icy winter days.


Your guide to choosing a versatile winter dress and how to style it best

Photo: PrettyLittleThing

PrettyLittleThing Recycled Stone Fitted Waist Long Sleeve Shirt Dress

You save £6.25 (25%)£25

Made using an innovative recycled yarn from plastic bottles, this shirt dress comes with a daringly short hem and a fitted design that flatters your waistline. Clean lines at the collar and cuffs make this an elegant piece that suits spring and summer perfectly.

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But with a few additions, you've got a smart winter dress perfect for the cooler months.

Transition it to winter: Wear with tights and chunky trainers for a more informal look.

Buy a dress you can layer

One of the best ways to nail dressing for winter is by incorporating layers into your outfit. Invest in crop cardigans or jumpers that stop just above your waist for a layered look that doesn’t make you look too shapeless.

Your guide to choosing a versatile winter dress and how to style it best

Photo: ASOS

ASOS DESIGN Knitted V Neck Midi Dress

The delicate neckline and side split make this ASOS buy a pretty warm-weather dress while its slim silhouette is flattering even if you’ve piled on a heap of chunky knits.

Transition it to winter: Pair with chunky boots and a cream or camel-hued cardigan for a sophisticated look.

Go for a knit dress for a little warmth

Knit dresses are one of the easiest pieces that can be tailored to the weather. Even lightweight ones will provide a little warmth that’s just right for chilly months but not stifling during warmer summery days.

Your guide to choosing a versatile winter dress and how to style it best

Photo: H&M

Collared Rib-Knit Dress

We can’t get enough of this fun pink mini-dress from high street giants H&M. Its short hemline is balanced tastefully with long sleeves, and the retro-style collar makes it totally trendy.

Transition it to winter: Wear with heeled boots and a thick pair of tights.

Buy something you can pair with a turtleneck

After you’ve invested in layers like cardigans, jumpers and shawls, don’t forget to pick up a turtleneck or two that could work well under your favourite dress. Fitted turtlenecks in block colours work best when under something strappy and simple.

Your guide to choosing a versatile winter dress and how to style it best

Photo: SHEIN

SHEIN Pocket Front Corduroy Pinafore Dress

You save £5 (41.70%)£11.99

Cheap winter dresses that are also versatile can be hard to come by.

Cute and preppy, this deep orange pinafore is brilliant for layering over long-sleeved or short-sleeved tops. It has a unique vintage quality thanks to its pockets and button detailing running down the front of the dress.

Transition it to winter: Pop it over a white or black turtleneck and pair with matching ankle boots.

Invest in rich colours

Deep, warm and velvety colours will forever and always be on-trend during the winter. But when paired with a mauve, burgundy or navy hue, you’ll have yourself a spring dress that's suitable any time of year, depending on the occasion.

Your guide to choosing a versatile winter dress and how to style it best

Photo: ASOS

Hope & Ivy Bardot Velvet Midi Dress

You save £30 (40%)£75

No matter the time of year, this party dress will do the trick. Its pretty neckline and bardot design make it a perfect piece for a winter wedding guest while its deep wine colour will look stunning at a Christmas party.

Transition it to winter: Wrap up and stay warm with a longline coat over this dress when you’re out and about.


Can you wear a dress in the winter?

While wearing a dress in the middle of winter might seem a little odd, it’s easy to style a dress so that it’s appropriate for cold weather. When shopping, try to take into consideration how you can revamp the piece to make it work for the different seasons.

How do you convert warm-weather clothes to winter wear?

Converting warm-weather dresses into winter wear isn’t as hard as you might think.

Investing in cardigans and tights is an easy way to update your spring/summer wardrobe. Alternatively, buying dresses that work well with boots or layered with jumpers is a smart move.

How to make a winter outfit more interesting

To elevate a winter outfit, we suggest focussing on sleek layering.

Opt for chic, monochromatic tones and try mixing fabrics like cashmere and silk for a luxurious feel. Finishing your look with a statement coat or pair of trendy boots can also work well.

Finally, incorporating minimalist jewellery and accessories will elegantly tie your look together.

What are the must-have winter clothes for women?

Essential winter clothes include a versatile coat, insulated boots, cosy jumpers and a trusty pair of jeans or thermal leggings.

Hats, scarves and gloves are a must for particularly chilly days when you need a little extra warmth.

And do consider investing in thermal layers for added warmth without the extra bulk.

What are the winter fashion trends for 2023?

From embracing red hues to power dressing and donning winter florals, the 2023 fashion trends are fun to play with this year. Some of our favourites include:

  • Metallic fabrics

  • Loose-fitting trousers

  • Lusciously soft textures

  • Quiet luxury

What is the best winter dress for women?

The dresses from this list we like best include the Mango Knitted Turtleneck Dress, the New Look Black Leaf Print Mini and the H&M Collared Rib Knit Dress.

However, we think any of the pieces recommended above would be an excellent addition to your wardrobe no matter the season.

The information presented above is accurate as of 22/12/2023. We are not responsible for any changes to the prices. The 'Best Buys featured' badge indicates sponsored content, and we may earn commission when you make a purchase.

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