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How To Wear A Dress In Winter Like A Fashion Insider

How to wear a dress in winter, when the wind is howling outside and the rain seeps into your bones?

When you think of winter wardrobe staples, you think chunky jumpers, puffer jackets and heavy boots. One thing that might not immediately come to mind is a dress. But, why not? Just because it’s cold outside, doesn’t mean you have to ditch the romantic, flowy silhouettes. All you have to do is style them a little smarter.

See for yourself below, and take inspo from street style experts to take on the colder months with flair.

How to wear a dress in winter

Layers, layers, layers

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Moritz Scholz

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Moritz Scholz

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Edward Berthelot

It’s not just a practical dressing tip: layering has been quite the trend in recent years, from skirts worn over trousers to tops peeking out from underneath each other, Miu Miu style. While your favourite lacy, silky, nightie dress might not offer much in way of warmth, when combined with other practical wardrobe staples it will provide a pop of fun and texture.

You could style it with a turtleneck underneath, tights and long boots for a more classic look. Or, if you want to go a little weirder, layer over jeans, pop on a cosy jumper and finish off with wintery finishes like a high-necked wool coat, moon boots and a fluffy headband.

Low Rise Loose Wide-Leg Jeans

Black Essential Ribbed Polo


Babushka, ya ya!

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Moritz Scholz

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WWD

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Christian Vierig

Another rising trend is the babushka scarf, wrapped around your head as if you’re heading to church or the market to buy some vegetables for soup. (My own grandma is Polish, so I’m rather well-versed in this aesthetic.) Or, perhaps you want to opt for the Old Hollywood strain of this style, with a silk scarf and sunglasses in a Brigitte Bardot cosplay. Or, another option still, you can opt for the balaclava which has risen in popularity over the past few years, transforming from the black ski mask to a girly accessory in bright colours and pastels, or encrusted in pearls a la Simone Rocha.

Wren Hooded Wool Scarf

Balabonnet


Bells and whistles

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305pics

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Raimonda Kulikauskiene

Accessories are an outfit’s best friend. A long-sleeved dress can be made more winter-appropriate with some trusty trimmings. Long, black leather boots are an obvious choice, since they offer both attitude and much-needed protection from the elements. Black leather gloves, too, enhance the look and can be styled with chunky bangles on top if you still want to make a statement while being wrapped up. Have fun with your hat choice, especially if the rest of your accessories are black. Something like the purple fuzzy hat above is cosy but show-stopping, since fashion doesn’t stop when the temperature drops.

Nancy Bonnet

Halton Over The Knee


Embrace the fluff

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Moritz Scholz

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Valentina Frugiuele

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Edward Berthelot

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Streetstyleshooters

A fluffy coat – in faux fur or a thrifted vintage model – is a classic for winter. With the swing towards maximalist, retro-inspired glamour, they’ve been even more popular as of late. It’s completely up to you what shade you opt for (I’m all for daring colours!), but neutrals like chocolate brown, ecru and white will obviously provide you with the most versatility. Boots are a sensible pairing for this look, and a pair of oversized sunnies will have you looking like you just stepped out of fashion week.

Annice Faux Fur Coat

Faux Fur Collared Longline Trench Coat


Wrapped in wool

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Hanna Lassen

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Christian Vierig

And, finally, why not opt for a knitted wool dress? While the rest of the entries on this list suggest how you might style a dress for winter, why not go straight to the source and buy a dress that is made from winter-appropriate materials? Cosy yet chic, the favourite shade this season is grey. Style with slouchy boots or riding boots, a chunky belt, a chainmail bag, and lots of silver jewellery. A slicked back hairstyle will complement the outfit perfectly, breaking up the long, straight silhouette.

Grey Ava Round Neck Knitted Dress

Long Dress


LP Staff Writers

Writers at Lord’s Press come from a range of professional backgrounds, including history, diplomacy, heraldry, and public administration. Many publish anonymously or under initials—a practice that reflects the publication’s long-standing emphasis on discretion and editorial objectivity. While they bring expertise in European nobility, protocol, and archival research, their role is not to opine, but to document. Their focus remains on accuracy, historical integrity, and the preservation of events and individuals whose significance might otherwise go unrecorded.

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