How To Style Dresses for Winter

Five key winter dress ideas to know about this season, from luxe velvet minis to cosy jumper dresses. Just add hard-working accessories and you're good to go

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Dulcie Emerson

A woman wears a grey winter dress and knee high boots

Master the winter dress and boots outfit formula

If you’re looking for versatility, a simple jersey column dress is what you need. It’s equally at home in the office, at weekend brunch or even on those spontaneous nights out. This ribbed column dress keeps things effortless, with a flattering shape and extra stretch for comfort.

If you’re unsure how to style dresses for winter, keep your line-up simple. Add heels and a sparkly grab bag for a quick lift, cinch in your waist with a statement belt or choose a faux fur coat and knee-high boots when the temperature dips.

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A woman wears a cream jumper dress with brown knee high boots and no tights

Cool-yet-casual dress outfits for chilly winter days

The jumper dress: winter's answer to effortless style and comfort. Made from cloud-yarn for a gorgeously soft feel and, this jumper dress lets you embrace chilly days without compromising on style. The creamy shade works with everything in your wardrobe, while adding a touch of lightness to you winter wardrobe.

Style it simply with tights and chocolate brown boots or layer it up for extra cosiness. Think thermal leggings or even a simple pair of straight-leg jeans. It's the perfect piece for staying stylish and snug all winter long.

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A woman wears a dark denim shirt dress and ankle boots, carrying a bag under her arm

How to wear dresses in winter? Just choose denim

A denim dress is the ultimate all-rounder: perfect for when you fancy a change from jeans, but don't want to stray too far from your comfort zone. A true year-round staple, a denim dress moves between seasons with just a few stylish tweaks.

We love this denim shirt dress - with its buttons and collared detail, it subtly nods to utility styling. Pair with ankle boots for a smart-casual look that'll take you everywhere, from a day in the office to a brunch date with friends. And if it’s feeling a bit chilly, throw on a cashmere polo neck underneath or some trusty thermals.

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A woman wears a short velvet mini dress, lacy tights and knee high boots

The best winter dresses for cosy glamour

We get it: when the temperatures drop, all you want to do is wrap yourself in soft, snuggly layers until spring. But with the right winter dresses, you can stay warm and feel instantly pulled together.

The secret is in the fabric. Velvet is not only luxurious but incredibly comfortable, and it’s far from a one-season wonder. It adds effortless polish to winter dress outfits without asking you to try too hard.

This Per Una velvet swing dress is the ideal throw-on-and-go piece for those evenings when you’d rather stay on the sofa. The relaxed swing shape keeps it comfortable, while its versatility means it can shift from day to night with ease.

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A woman wears a dark floral ruffle dress, black boots and carries a burgundy handbag

Scene-stealing winter dress outfits for those special events

Whether you’re heading to a winter wedding or marking a milestone birthday, this Monsoon floral dress guarantees you’ll feel confident and well-dressed. The fluid shape moves beautifully, while the darker florals keep things seasonal and easy to wear.

It also lends itself perfectly to a stylish winter dress and boots outfit. Pair it with black suede kitten-heel boots for a refined take on winter dressing. Add thermal tights for extra warmth, then finish with gold earrings and a faux leather clutch for a touch of evening-ready shine.

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Published 12.15.2025