Dress Up: Mini, Midi and Maxi Styles for Day, Night and Everything In-Between This Winter

Photo: Courtesy of Maggie Marilyn

Lean into the long black dress, don’t shy away from printed pieces and put your knee-high boots to work with higher hemlines. These are the dresses you’ll want to wear all season long.

Have you found yourself in a jumper-jeans-boots repeat outfit rut? Same. We might have passed the winter solstice but there are still plenty more chilly days ahead.

I challenge you to put down the denim and remind yourself how fancy it feels to wear a winter dress. The one-and-done appeal actually makes your morning routine easier. And if you’re worried about warmth, this is a safe space to talk about strategically layering Uniqlo Heattech or your favoured thermals.

Day

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Knit dresses are a no-brainer. Subtle florals remind us that spring will eventually arrive. And backless styles simply need to be layered with a fine knit and fleece-lined stockings – this is also the time to make the most of your knee-high boots with mini hemlines.

Jillian Boustred Chloe Dress

$450 Jillian Boustred Chloe Dress A brand signature, this ribbed silhouette is the perfect 9 to 5 outfit. Not too cosy (thanks to a cotton construction) for office heating. Not too cold (thanks to long sleeves and a maxi hemline) for the arctic outdoors. Just right.

Kowtow Yves Shirt Dress

$329 Kowtow Yves Shirt Dress Long sleeves and a long hemline. Are you sensing a theme here? This cotton poplin style wouldn’t look out of place with a turtleneck layered underneath its collar.

Wynn Hamlyn Edie Macramé Mini Dress

NZD$250 Wynn Hamlyn Edie Macramé Mini Dress Long sleeves and a short hemline. This one is made for your knee-high boots. Or a pair of sheer tights and Mary Janes. There’s also a top version if you can’t quite give up the wide leg denim.

Alemais Gisela Dress

$725 Alemais Gisela Dress These balloon sleeves will hide anything you want to layer under them. And if you’re heading to Europe at this time of year, they’ll make the perfect partner to spritz-filled hands.

Sir Libertine Midi Dress

$440 Sir Libertine Midi Dress Wear this red floral style with the scoop to the back as you layer up in coats and cardis. And then turn it around and show off the matching bralette on your next holiday.

Night

The events don’t stop just because it's cold and dark outside, so let the long black dress reign this winter. Sequins and sheet silhouettes are another option if you’re looking to heat up evening affairs.

A Emery Lowe Dress

$550 A Emery Lowe Dress The ultimate one-and-done dress, this maxi silk style oozes elegance. Pearl earrings, pointed-toe pumps and a tiny handbag is all you need to add at any time of the year.

Christopher Esber Open Twist Anglaise Dress

$800 Christopher Esber Open Twist Anglaise Dress An Esber signature, this twist-front style could always be layered with a contrasting top underneath if needed. And there’s this purple beaded mini if you’re willing to forgo a bit of warmth in the name of fashion.

Harris Tapper Mira Lace Dress

$615 Harris Tapper Mira Lace Dress You don’t have to dismiss the naked dress just because it’s winter. Because you’ll be the hottest thing in the room. Also, if you’re not sick of me saying this: layer, layer, layer.

Paris Georgia Audrey Dress

$990 Paris Georgia Audrey Dress There’s no formal evidence that sequins conduct heat. But wear this one with a faux fur jacket and see what happens. Don’t make me say mob wife.

Somewhere in-between

You know those styles that can go either way – wear them with sneakers or flat boots to the office and add a kitten heel to take them to cocktail hour. Some of these styles wouldn’t be amiss at winter weddings and others can pull double duty at any time of year.

Camilla & Marc Litha Dress

$550 Camilla & Marc Litha Dress The neckline says night but the cotton construction adds a casual air to this one. Lean into the moment for red and double down with your accessories. Pumps or flats. Boots or dad sneakers. Dealer’s choice.

Maggie Marilyn Slow Dancing Dress

$895 Maggie Marilyn Slow Dancing Dress Maggie Marilyn is the master of modern whimsy. Layer this silk style with a white turtleneck sweater for winter weddings, letting it shine on its own once spring events roll around. This vintage-inspired tweed mini is a good choice if you’re looking for sleeves.

Friends With Frank The Liberty Dress

$449 Friends With Frank The Liberty Dress A ’90s slip is never a bad idea. Wear this one with minimalist boots or embellished pumps depending on the occasion.

Lucy Folk Eos Embroidered Dress

$3400 Lucy Folk Eos Embroidered Dress Another one to layer with a turtleneck, thermals and knee-high boots – we’re not so silently obsessed with this statement pair from St Agni. Lucy Folk is always a good reminder that summer will come again.

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