If you work in an office, you’ll likely be familiar with the phenomenon that takes place most mornings whereby you open your wardrobe and stare into it for a good five minutes as you wonder what you’ll wear to work that day.
For some, the separation between work wardrobe and casual attire forms a clear divide, but for others (arguably the luckier group) the two overlap like a stylishly curated Venn diagram.
And yet, no matter which column you fall into, finding chic work-appropriate outfits can feel like an endless struggle.
Whether you’re in a corporate or casual setting, opting for work dresses that seamlessly transition through the cooler season, possessing the ability to be worn alone or layered on particularly icy days, always prove a worthy investment.
Below, we’ve found the best winter work dresses to shop this season for every workspace.
The best winter work dresses for 2024
01
Isabel Marant Ulani Asymmetric Crepe Midi Dress
$1495 at Net-A-Porter
If you want to embrace colour this winter but still stay within the seasonal colour palette, this flirtatious midi from Isabel Marant is our top pick. It embodies French-girl chic and is ideal for layering as the temperatures start to drop.
Sizes: 6 – 16 size range | Colours: Plum graphic print | Materials: 65% Viscose, 35% Silk
Key features:
- Draped bodice
- Lightweight crepe material
- Asymmetric hem
02
Riba Mini Blazer Dress
$950 at Camilla & Marc
A pristine white winter dress is the ultimate statement piece. This elegant cream blazer dress is office-appropriate but transitions seamlessly to drinks after a long day’s work.
Sizes: 6 – 14 size range | Colours: Cream | Materials: 100% Polyester
Key features:
- Peaked lapel
- Mock welt pocket
- Fitted silhouette
- Button closure at centre
Available at:
- $950 from The Iconic
- $950 from David Jones
03
Annex Wool Midi Dress
$480 at Jac & Jack
A knitted dress is a winter wardrobe essential, and if you’re in search of a lightweight, high-quality wool option, Jac & Jack’s Annex midi dress is a standout choice. Its construction avoids the bulky, heavy feel, making it versatile for trans-seasonal wear and perfect for layering as the temperature drops.
Sizes: 6 – 14 size range | Colours: Charcoal Melange Grey and Navy | Materials: 100% Merino wool
Key features:
- Midi length
- Crew neckline and long sleeves
- Lightweight Merino wool
04
DÔEN Kira Belted Pussybow Mini
$713.97 at Net-A-Porter
Florals for spring? Boring. Florals for autumn and winter, however, we can get on board with. This elegant mini dress from LA-based label DÔEN is perfect for the colder seasons. Expertly layer it with sheer tights and knee-high boots when the temperatures drop, but don’t be surprised if you find yourself reaching for it year-round.
Sizes: 4 – 14 size range | Colours: Red floral pattern | Materials: 100% Silk
Key features:
- Lightweight silk georgette material
- Self-tie belt
- Pussybow at neck
05
Zip Detail Jersey Midi Dress
$325 at Cue
With a statement zipper right up the centre of the dress, you can take this from the boardroom to the bar with ease. Its expertly cut design hugs the figure, accentuating your curves in all the right places.
Sizes: 6 – 16 size range | Colours: Black | Materials: 100% Viscose
Key features:
- Form-fitting silhouette
- Full-length sleeve
- Funnel neckline
Available at:
- $325 from The Iconic
- $325 from David Jones
06
Minima Esenciales Cove Cashmere Blend Sweater Dress
$260 at The Iconic
A classic sweater dress is the perfect low-effort, high-impact winter ensemble. Made from a luxurious Merino wool and cashmere blend with contrast statement stitching, this piece feels elevated yet will keep you comfy and cosy all day.
Sizes: 6 – 18 size range | Colours: Black and Cream | Materials: 47% Merino wool, 38% Viscose, 10% Nylon and 5% Cashmere
Key features:
- Bateau neckline
- White contrast stitching on shoulders and side
- Full-length sleeves
07
Alemais Evergreen Printed Dress
$901 at Farfetch
Designed in collaboration with Meagan Boyd, the print on this stunning shirt dress is the splash of colour our winter wardrobes need and makes for a timeless piece that could be worn from your desk to dinner and even on your Amalfi Coast vacay.
Sizes: 4 – 8 size range | Colours: Green Multicolour | Materials: 100% Ramie and 100% Cotton lining
Key features:
- Straight point collar
- Balloon sleeves
- Front button fastening
08
Monument Long Dress
$1295 at Christopher Esber
Designed in a way to give the effect of a silk maxi skirt and the perfectly oversized knit jumper, this opulent piece is a worthy investment piece you’ll find yourself wearing year after year.
Sizes: 4 – 14 size range | Colours: Black, Cocoa and Light Steel | Materials: 100% Cashmere and 100% Silk
Key features:
- Long sleeves and crew neckline
- Maxi length skirt
- Relaxed, oversized fit
09
Printed Crepe Mini Dress
$375 at Ganni
Look Copenhagen-cool with this mini dress from cult-label Ganni that is just perfect for the office without feeling boring or stuffy. The unique monochrome floral print adds a point of interest, while the timeless silhouette ensures versatility.
Sizes: 4 – 14 size range | Colours: Black Print | Materials: 50% Lenzing™Ecovero™, 50% Viscose
Key features:
- Shorter puff sleeves
- Round neckline
Available at:
- $315 from Mytheresa
How do you make a winter dress work?
Taking your dresses from summer into the cooler seasons is easier than you would think. Instead of pairing your pieces with strappy sandals, turn to knee-high boots that add warmth alongside layers like tights and thermals if the weather calls for it.
Don’t forget the ultimate everyday coat that you can throw over your shoulders on extra chilly days, layering your dresses also adds a level of dimension and texture to your winter outfits.
Looking to save money on your winter wardrobe? Check out our coupon codes for Net-A-Porter, The Iconic and more.
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- 8 Pairs Of Bootcut Jeans Deserving Of A Place In Your Winter Wardrobe
