Mini, Midi and Maxi Dresses for Day, Night and Everything In-Between This Winter

Photo: Courtesy Of Sir

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

Words by Simone Richardson · Updated on 08 Sep 2025 · Published on 15 Jul 2025

Have you found yourself in a jumper - jeans - jacket 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 preferred thermals.

Maxi dresses for winter

Long hemlines don’t mean forgoing shape or structure. These floor-grazers are built for layering, with fluid silhouettes, cut-out detailing and heavyweight knits for details steeped in cool-weather credibility.

Marle Foundations dress

$400

Bring a colour hit to your cold-weather wardrobe with this plum-toned style from the New Zealand label. It’s cut from a soft cotton blend for a fluid drape, with contrasting ivory buttons down the front. Pair with ballet flats – or layer over trousers for a refined take on the re-emerging 2000s trend.

Buy at The Iconic Buy at Marle

Sir Lisander long sleeve dress

$550

Sheer polka dots soften the long-line silhouette of this floaty Sir style. It comes with a removable black slip – so you can lean into layering now and pare it back once the weather warms.

Buy at Sir

St Agni Bateau cut out dress

$400

The Byron Bay label’s signature restraint shows in the contrast between a knitted bodice and crisp cotton-poplin skirt. A boat neckline and ruched waist deliver shape, while the mixed textures do the styling for you.

Buy at St Agni Buy at End

Kowtow T-shirt Swing dress

$189

From the Kiwi label’s core Essentials range, this A-line dress is cut from soft organic cotton jersey with dropped shoulders and wide sleeves for extra ease. A woven belt lets you cinch the waist if you’re after more shape.

Buy at The Iconic Buy at Kowtow

Midi dresses for winter

There’s a reason this is the most versatile length. This season, midi dresses lean into texture and tailoring, with long sleeves and details that invite movement. Layer on top of – or below – sheer layers, soft tailoring and contrasting palettes.

Kahe I’m Hooked dress

$347

From slow-fashion label Kahe, this cotton–silk style features raw-edged hems and corset-inspired seams for an ethereal finish. The sheer fabrication makes it a natural pairing with black barrel jeans, or you can fasten the hook-and-eye closures all the way down and layer it with a slip to wear as a dress.

Buy at Kahe

Kloke Patch dress

$398

Thanks to denim, blue feels like an approachable way to add colour to a winter wardrobe. Kloke leans into the easy-wearing palette with a blocked patchwork of sky and indigo. The 100 per cent cotton style has white contrast seams, an oversized fit and just the right amount of structure to wear on repeat.

Buy at Kloke

All Is A Gentle Spring The Eternal dress

$1350

Melbourne designer Isabelle Hellyer draws on 1800s corsetry and ’80s activewear for her sculptural silhouettes. This double-weave silk–wool design features a spiral-boned bodice and subtly exaggerated hips – a 2025 take on historical shape-building techniques.

Buy at All Is A Gentle Spring

Proenza Schouler White Label Layla dress

$359.25

This midi from NYC label Proenza Schouler doesn’t shy away from structure. It’s cut from a stretch tailoring fabric with an ink-hued check and features a cinched waist that drops into a flared skirt and asymmetric hem.

Buy at The Iconic

Mini dresses for winter

The secret to pulling off a mini in cold weather? Weighty fabrics, clever layering and an epic pair of leather boots. These styles hold their own under wool coats and over textured tights – but work just as well bare-legged on bolder days.

Henne Lyra Knit dress

$289

A staple of the brand’s ongoing rotation, the Lyra is back in black – and in a new rich chocolate. Cut to a mini length but made from a wool-blend knit, it features a high neck and voluminous balloon sleeves, making for a reach-worthy essential in any winter wardrobe.

Buy at Henne

Elka Collective Amber Knit dress

$299

A single colour, but far from simple. This cotton-blend mini features exposed seams and a soft funnel neck for serious design appeal. It’s pared back enough for loafers by day, but easily elevated with heels for dinner.

Buy at The Iconic Buy at Elka Collective

Courtney Zheng Dana mini dress

$640

Preppy, but grown up. Emerging designer Courtney Zheng reimagines the school uniform, giving it timeless appeal. Made from 100 per cent wool, this tailored mini features a structured pinafore-style neckline, pleated skirt and a drop waist with matching belt. It nods to the ’90s which, naturally, reads as right-now.

Buy at The New Trend Buy at Courtney Zheng

Wynn Hamlyn Utility Vest mini dress

$385

This is part of the designer’s SS25 collection, but it calls for winter layering. The tailored style blends elements of suiting and utility wear, with oversized patch pockets and a clean finish. Fully lined and crafted using a neutral mushroom tone, it works well over a black skivvy and tights or layered under a heavy wool coat.

Buy at The New Trend Buy at Wynn Hamlyn

Additional reporting by Alice Jeffery.

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About the author

Simone is Broadsheet's shopping editor.