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23 Oct These Autumn Winter Dresses are Perfect for Transitional Dressing

Posted at 13:01h in Dresses, Fashion, Seasonal, Wardrobe staples by

There is nothing more exciting at the start of a new season than wardrobe planning. OK, there are potentially more exciting things, but when you’re heading into autumn/winter, conjuring up snug outfit concoctions is surely a highlight. Digging out some beloved cosy autumn treasures after a summer sans layers (yes, I know that part is tricky to let go of…) can really get the creative juices flowing for the season ahead.

And, with great layers, comes great possibilities. The scope for reinvention come the new season is like a clean slate for your wardrobe. Which, arguably can be somewhat overwhelming on occasion. This is where dresses come in. As a category, dresses can always be relied upon for a great reward vs. effort ratio. Slip into one single piece and you are pretty much good to go out the door, with the addition of a few choice accessories.

This season plump for a trending maxi dress, a classic midi, wear-anywhere denim number, or an autumnal hue, all are perfect autumn winter dress options for easy transitional dressing. Layer with a roll neck, knee high boots and bare legs on milder days and bring on the cosier layers when things get nippy.

The Ultimate Transitional Autumn Dress – Midi Dresses

Midi dresses might not be a headline trend, but they are an ultimate classic we will never stop wearing. Perfect paired with socks and loafers or layered with knee high boots, a midi dress will never fail you.

An elegant silhouette meets a statement scarlet shade to create this panelled midi dress. Crafted from modern crepe with a flattering fluid drape, it's an effortless office and occasionwear solution.
Me + Em Elegant Panelled Midi Dress Modern Crepe, £250.00

In this seasons biggest colour trend and a gorgeous silhouette.

The silhouette of this dress riffs on a signature style from the COS archives. Designed to highlight the form, it has gathers at the hips that create soft ruching, a subtle boat neckline and an asymmetric hem. It's offered in an enduring black shade and crafted from satin that has a subtle sheen.
COS ASYMMETRIC GATHERED SATIN MIDI DRESS, £110

Update your black midi with an asymmetric twist this season.

Zara polka dot Midi dress made of viscose. Round neck and long sleeves with a flared hem. Creased fabric detail. Invisible back zip fastening.
Zara ZW COLLECTION CREASED POLKA DOT DRESS, £49.99

Polka dots have been reemerging amongst streetstylers this fashion month. Reignite your love with this chic crinkled midi dress.

Raey’s black sweatshirt dress will impart a contemporary mood to your off-duty edits through its oversized construction. It’s made from a recycled-cotton blend then finished with a ribbed crew neckline, raglan sleeves and side-slip pockets.
RAEY Recycled-yarn cotton-blend sweatshirt dress, £250

Raey’s black oversized sweatshirt lets you take your loungewear game beyond the house.

Gabriella, the bestselling ALIGNE dress, has had an autumn/winter make-over in our new true-to-size fit. It’s the kind of easy dress that always leaves you looking put-together, but without all the effort. Crafted from deadstock cord and finished in a beautiful, rich toffee shade, it’ll carry you through the cold(er) months. Complement with your favourite boots for an elevated look.
Aligne GABRIELLA CORD ZIP NECK MIDI DRESS, £129.00

You know the amazing denim version of this classic throw on midi. Keep yourself notified for the return of this Autumn take from Aligne.

Valentino's elegant approach is communicated through the house's concise tailoring. The Cady Couture dress is made of blue silk and boasts a self-tie gathered panel that offers soft dimension to the button-up bodice.
VALENTINO Cady Couture silk shirt dress, £3,450

This colour is dreamy.

The Trending Autumn Winter Length – Maxi Dresses

If you want an update for your classic midi, then the maxi dress is the way to go. This trending length is going nowhere fast as the SS24 catwalks proved, and provides a little extra glamour to your cosiness this season.

Reformation Olive Sai dress is a perfect autumn midi dress with a mock neck, no sleeves and a full skirt.
Reformation Sai Dress, £228

So pretty. This olive wonder could work in any season and also comes in black.

& Other Stoires Knitted boat neck midi dress crafted from a blended material. Designed with three-quarter-length sleeves in a straight, midi-length silhouette. The back features a scooped neck with a tubular tie detail.
& Other Stories Knitted Boat Neck Midi Dress, £75

Perfect for the minimalists out there.

A forever investment, this V-neck maxi dress is crafted from elegant pure silk in a versatile neutral hue and features our signature intelligent design details for styling versatility and a flattering fit.
Me + Em Silk Statement V-Neck Maxi Dress + Belt, £550.00

This dramatic black maxi also comes in red.

A subtle black-lace trim outlines this ankle-grazing dress's V-neckline and bodice, adding texture and depth to the style's satin-back crepe with an elegantly soft drape.
Me + Em Satin And Lace Full-Length Slip Dress, £295.00

Me + Em’s navy and black lace edged slip is so gorgeous. It also comes in cream and black.

Raey’s ivory dress is characterised by raw-edge seams that run diagonally across the wool frame and frayed edges along the hem and neckline.
RAEY Raw-edge sleeveless wool dress, £525

Layer this chic cream wool maxi over a roll neck and knee high boots to brave the autumn/winter chill. It also comes in black.

Alignes leopard print dress Kylie slip dress is designed in a statement-making leopard that's going to steal all the attention wherever you go. Designed in a flattering maxi length with a v-neck and spaghetti straps, it can be worn on its own or paired with a leather jacket or layered with a top for a more relaxed look.
Aligne KYLIE V NECK SLIP DRESS, £119.00

Leopard print is so classic and this will be equally great layered with a knit in winter, as worn alone with sandals in summer.

This roll-neck dress marries two key trends for the upcoming season: power shoulders and maxi hemlines. It's knitted from pure merino wool that's luxuriously soft and shaped to highlight the form before flaring out to an exaggerated flared hem. The shoulder pads can be removed should the occasion call for something a little more pared back.
COS POWER-SHOULDER MERINO WOOL MAXI DRESS, £115

So chic. Is it Saint Laurent, or COS?

The Autumn-Ready Prints – Dark Based Print Dresses

Dark florals trend pretty much every autumn/winter, and this season is no exception. If you’re not a fan of florals, then try a classic animal print that will never fail you.

H&M Short dress in softly draping satin with a collar and buttons down the front. Long balloon sleeves with buttoned cuffs, narrow elastication at the waist and a straight-cut hem. Unlined.
H&M Satin shirt dress, £18.99

Easy peasy.

Cementing floral prints in your autumn wardrobe, this long-sleeved dress features our bespoke Scribble Flower print in a combination of navy and khaki set on a black backdrop.
Me + Em Scribbled Floral Print Fit and Flare Maxi Dress, £195

The zip detail on Me + Em’s pretty dark floral dress adds a point of difference.

& Other Stories black Mock neck mini dress featuring gathered shoulders and long cuffs.
& Other Stories Mock Neck Midi Dress, £75

A great style for showing off your best knee-high boots and flashing a little thigh whilst the weather still allows.

& Other Stories Frill midi dress crafted from a silk-like fabric. Designed with a v-cut neckline decorated with frilled detailing and a buttoned front with a plain bodice tied with a thin belt at the waist. The skirt is embellished with cascading frills.
& Other Stories Frill Midi Dress, £175

A little bit gothic and plenty romantic.

Arket Midi dress with long sleeves crafted from a bias-cut Ecojilin and Ecovero viscose weave. Babylock finishes and darts at bust.
Arket Bias-Cut Midi Dress, £97

This is such a great printed all rounder. This Mango dress has a similar feel and also comes in sizes 4-26.

Raey's multicoloured dress is shaped in the UK from silk that's enlivened with a floral chrysanthemum print. It's shaped to a V-neckline and features a gathered waist and cropped sleeves.
RAEY Chrysanthemum print elasticated-waist silk dress, £495

Perfect for any season, and occasion.

The Best Cold Weather Dresses – Knit Dresses

What could be more comforting than swathing yourself in knitwear come colder days? Nothing, that is what. And what better way to do it than a chic knit maxi, or cosy chunky cable knit mini?

Spun from recycled cashmere and wool, Raey’s navy dress features a deep V-neckline, dropped shoulders and a floor-grazing length for a relaxed mood.
RAEY Cashmere-blend deep V-Neck dress, £425

Raey’s cashmere blend maxi knit is so cosy and chic all at once.

Keep warm with the Aligne Kyrony dress. Designed for a relaxed feel, it's a versatile piece that can be worn on its own with knee-high boots or paired with a pair of wide-leg trousers for everyday dressing. The design features cable detailing, wide sleeves and is finished in subtle camel colour.
Aligne KYRONY CABLE FUNNEL NECK DRESS, £149.00

Show off your new season boots in this knitted mini dress.

Introducing a gilded touch to an occasionwear favourite, this LBD is woven with glittering gold-toned threading that works its way vertically over the softly knitted fabric that gently hugs your frame for a structured yet comfortable fit.
ME + Em Fashioned Rib Metallic Fit and Flare Midi Dress, £225.00

This metallic stripe detail knit dress is ready for after-dark.

& Other Stories black Relaxed mini knit dress featuring a mock neck and a tonal buckle belt.
& Other Stories Belted Mini Knit Dress, £55

A cinched or belted silhouette is a trend that isn’t going away this season, or next.

& Other Stoires deep green Flared midi dress knitted from a wool-blend, featuring an allover ribbed finish.
& Other Stories Flared Rib Midi Dress, £110

The colour…

The Autumn Winter 2023 collection is peppered with fringed accents for texture and movement. This black midi dress is crafted from 100% RWS-certified wool and knitted in rectangular panels that are stitched together to create a quilted effect. It's finished with knotted tassels at the hem.
COS FRINGED PANELLED WOOL MIDI DRESS, £135

Tap into one of this (and next) seasons most fun trends with a little unexpected fringe action.

Mango cream knit midi dress with mock neck and long sleeves. It has a form fitting silhouette and a rib knit.
Mango Perkins-neck ribbed dress, £35.99

So chic.

Arket black rib. knit maxi dress with high neck and relaxed fit.
Arket HIgh Neck Rib Knit Dress, £129

Staple.

H&M striped Ankle-length, fitted dress in a soft rib knit with a round neckline, long sleeves and a gently flared skirt.
H&M Rib-knit dress, £32.99

The uneven stripes make this H&M knitted midi dress stand out from the other Breton knits.

The Timeless Staple – Black Dresses

A black dress is the ultimate wardrobe staple for any season, and any occasion.

Arket black Dress crafted from a smooth satin weave of pure silk. The bias-cut fabric gives a natural stretch to the style. Slim fit.
Arket Silk Slip Dress, £129

A trans-seasonal special.

Arket black Long-sleeved dress with frills at centre seam and at back of sleeves. Standing collar with a visible button and slits at sides. Boxy shape.
Arket Black Frill Dress, £87

If it’s slightly Wednesday Addams, it’s very on-point.

Raey produces minimalistic wardrobe staples such as this black oversized slip dress, constructed from panels of lightweight silk satin with a fluid drape.
RAEY Oversized panelled v-neck slip dress, £250

A slip is the ultimate in versatility.

zoomed image favourites.icon.add.accessibility SCARF-DETAIL MAXI DRESS £115 COLOUR BLACK EU SIZE 32343638404244 SIZE GUIDE ADD TO BAG FIND IN STORE DESCRIPTION-DELIVERY & PAYMENT-DETAILS Taking inspiration from '70s styles, this dress has an oversized neck scarf that cascades all the way down to the maxi skirt – wrap it around your neck or drape it over one shoulder. It's crafted from a fluid ECOVERO™ viscose blend and shaped for a relaxed silhouette that's enhanced by the dropped, curved hem.
COS Scarf Detail Black Maxi Dress, £115

70s vibes with a very AW23 scarf detail.

H&M Long, fitted, sleeveless lace dress with a V-shaped neckline at the front and back. Concealed zip and hook-and-eye fastener at one side and a wide, asymmetric flounce below the hips. Lined.
H&M Flounced lace dress, £44.99

H&M’s black lace dress has witchy vibes in a good way. Layer over a roll neck for a more winter hardy take.

Raey's black dress is draped from heavy double-faced silk and shaped with a cowl-neck, dolman sleeves and an open back.
RAEY Cowl-neck silk dolman dress, £395

A dress that can take you from day-to-night.

H&M black Ankle-length dress in a pleated weave made from a viscose blend. Long, flared sleeves and a wrapover front with a deep V-neckline and a wide tie belt at the waist. Unlined.
H&M Pleated wrap dress, £32.99

This looks so easy to wear.

The Multi-Tasking Dress – Denim Dresses

If you find it hard to prise yourself away from your jeans, take baby steps with a denim dress you can wear just as easily going into autumn/winter as you can heading into spring. Plus, a denim dress can be worn in so many ways.

Denim takes on a new direction in our Autumn Winter 2023 collection. Washed a faded light-blue shade, this Western-inspired shirt dress is designed with a double-layered yoke, a pair of flap pockets and a maxi-length hem with a high slit. Style it with cowboy boots and one of our signature bags.
COS DENIM MAXI SHIRT DRESS, £135

Make it statement in this COS denim shirt dress.

This Me + Em denim midi dress is a versatile autumn investment, this denim dress is shaped to a midi length and features a line of buttons through the centre to adjust the neckline and accommodate base layers when temperatures start to drop.
Me + Em Denim Midi Dress + Belt, £250.00

This denim midi has a 70s feel.

Reformation The Kendi Denim Midi Dress is a slim fitting midi dress with wide straps, crew neck and back zipper.
Reformation Kendi Denim Midi Dress, £228

A sassier take on the staple denim dress.

No wardrobe is complete without a timeless wear-with-anything denim dress. Flowy, elegant and with lots of volume in the sleeves, Hibiscus is the perfect dress for the office and beyond. Wear with your favourite sandals for a relaxed take, or layer with a pair of wide leg trousers for a statement look.
Aligne HIBISCUS DENIM BUTTON VOLUME SLEEVE MIDI DRESS, £119.00

This will work just as well going in and out of winter.

Khaite's minimalist designs exude modern sophistication and effortless elegance. The Franka maxi dress is made from light blue cotton denim and has pitched sleeves, curved seaming, and an open collar.
KHAITE Franka cotton denim maxi dress, £800

Khaite’s cool denim dress looks fabulous with elevated cowboy boots.

H&M Short dress in sturdy denim with a collar, buttons down the front and a yoke at the back. Detachable tie belt at the waist and long puff sleeves with buttoned cuffs. Visible seams down the front and back. Unlined.
H&M Tie-belt denim dress, £37.99

Pair this with knee-high boots for transitional days.

Every wardrobe needs an easy throw-on-and-go denim dress. Crafted from 100% organic cotton that uses 80% less water than regular denim, Kierfer is that dress. Designed for a flattering midaxi silhouette with contrast top-stitching and paneling, it’s the kind of piece you’ll want to reach for again and again.
Aligne KIERFER MIDAXI DENIM DRESS, £149.00

Such a great autumn wardrobe staple.

The Trending Colours – Autumnal Hues

We all know red is trending hard, but her more autumnal (and some may say wearable) sister burgundy is also big news for autumn/winter and spring/summer 2024. Shades of cinnamon and chocolate brown are also high on the fashion hit list for cosy autumn/winter days this season.

Gitty is an ALIGNE classic. Crafted from buttery-soft chrome-free leather, it's a midi length dress with a flattering, straight fit and self-tie belt to cinch the waist. Perfect for the office and beyond, it can be styled with just about anything and is the kind of forever piece that transcends seasons.
Aligne GITTY LEATHER SHIRT DRESS, £289.00

Aligne’s chocolate/burgundy leather midi shirt dress is so good. I am also a big fan of the denim version.

H&M burgundy Calf-length, fitted dress in a rib knit made from a LivaEco™ viscose blend. Sweetheart neckline, long sleeves with gently flared cuffs, and a straight hem.
H&M Rib-knit dress, £32.99

This winning burgundy rib knit dress comes in XS-4XL and a petite range.

Reformation burgundy floral midi dress. Mock neckline, side slit, long sleeves and tapered waist.
Reformation Castalia Dress, £298

This autumnal floral could easily be dressed up or down.

Raey cuts this burgundy dress from textured washed silk to an elegant silhouette that’s gathered at the waist before falling to a front-slit hem.
RAEY Gathered waist silk wrap dress, £395

Raey’s deep burgundy dress cut from textured washed silk would look great worn alone or layered over a second-skin knit.

In an homage to Erdem's Bloomsbury home and its Victorian wallpapers, this dress is made from burgundy cotton faille and decorated with the Gilman Iris print. The abstract floral detailing complements the fitted waist and full, midi-length skirt on this whimsical design.
ERDEM Floral cotton faille midi dress, £1,995

Full skirts are trending.

Reformation chianti cashmere sweater midi dress is designed to be fitted at bodice and waist with a relaxed skirt
Reformation Evan Cashmere Sweater Dress, £378

This cashmere sweater dress comes in this Chianti shade, or grey.

H&M Short dress in a viscose crêpe weave with a collar and buttons down the front. Gently dropped shoulders, long balloon sleeves with buttoned cuffs, a fitted bodice and a flared skirt. Unlined.
H&M Crêpe shirt dress, £32.99

Pumpkin spice anyone?

This story was published at an earlier time and has since been updated.

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