When I say that winter is my favourite season to dress for, it comes with a caveat: it’s only my favourite when I have the time to do it justice.
If my morning is slower, I revel in layering up merino tops and cashmere layers, mixing and matching knitwear and satins and indulging in playful accessories like cosy mittens and sleek scarves. But at the busiest time of the year, those languid mornings are few and far between, and getting dressed during winter can feel like an added task that our extensive to-do lists simply don’t need. My solution? The winter maxi dress.
Easy to throw on and even easier to style, it’s a piece that will consistently serve your wardrobe when the temperatures drop. Whether you’re facing a day in the office, a stroll to your favourite coffee shop or even an evening out, let a maxi do all the heavy lifting this winter.
The elegance of a maxi silhouette speaks for itself, so you don’t have to do much to form a seriously put-together look when you only have five minutes to get ready. For the day, simply slip on boots or flats with a dash of classic jewellery and you’re all set; and for the evening, swap in mules or heeled boots for a more elevated appeal. Finally, call upon your trusted winter coat to pull the ensemble together and you’re ready to take on the day, come rain, shine or even snow.
Taking inspiration from some of our favourite fashion people, I’ve separated the best winter maxi dresses into four categories, covering the most popular, wearable and timeless styles around.
Keep scrolling to explore them now.
The Best Winter Maxi Dresses
1. The Best Knitted Winter Maxi Dresses
Style Notes: For those who always want to be cosy, a knitted dress is ideal, and if you choose an elegant silhouette, it can easily transform for the evening as needed.
Shop the Best Knitted Winter Maxi Dresses:
COS
Brushed-Cashmere Maxi Dress
If cosy and chic is what you’re looking for, meet COS’s brushed cashmere maxi dress.
A.W.A.K.E. MODE
Off-The-Shoulder Knit Maxi Dress
I adore everything about this dress.
Hush
Tilly Tie Waist Merino Wool Midi Dress
Norma Kamali
Knitted Maxi Dress
From the bold shoulders to the softly draped pleats, there’s a lot to love about this dress.
MANGO
Knitted Turtleneck Dress
For a more affordable option, look to this classic offering from Mango.
GUEST IN RESIDENCE
Ribbed Cashmere Turtleneck Maxi Dress
2. The Best Evening Winter Maxi Dresses
Style Notes: With plenty of parties, drinks events and celebrations on the horizon, I’ve whittled down a selection of compliment-inducing maxi evening dresses that are ready to become your go-to “going out dress.”
Shop the Best Evening Winter Maxi Dresses:
Reformation
Nemy Knit Dress in Pine Tree
This also comes in deep red and classic black.
TOVE
Silk Jenna Maxi Dress
You’ll wear this every season.
E.STOTT
Silk-Crystal Cleo Gown
Just wait until you see the back.
ZARA X Kate Moss
Scarf Dress
I can’t believe this is still in stock.
STELLA MCCARTNEY
Ruched Stretch-Jersey Maxi Dress
Sometimes, simple ruching is all that’s needed for a highly elegant look.
Reformation
Anaiis Silk Dress
Reformation always excels in the dress department.
Toteme
Evening Jersey Maxi Dress
I have a feeling this will become a new Toteme icon.
3. The Best Black Winter Maxi Dresses
Style Notes: The Little Black Dress can take a break whilst the Long Black Dress steps in. You can’t go wrong with any of these picks.
Shop the Best Black Winter Maxi Dresses:
COS
Cowl-Neck Long-Sleeved Maxi Dress
A black maxi dress with black accessories is so elegant.
Anna Quan
Phoebe Off-The-Shoulder Knit-Cotton Maxi Dress
Off-the-shoulder necklines are trending right now.
& Other Stories
A-Line Maxi Dress
A style you’ll wear all year round.
COS
Dropped-Waist Jersey Maxi Dress
RIXO
Losanna Velvet Maxi Dress
Hush
Talen Long Sleeved Knitted Maxi Dress
For evening, I’d add oversized gold jewellery and a matching chain belt.
4. The Best Patterned Winter Maxi Dresses
Style Notes: If monochromatic palettes just won’t do, there’s an array of playful prints ready to join your winter wardrobe immediately. From florals to stripes, these contenders will stand the test of time.
Shop the Best Patterned Winter Maxi Dresses:
FAITHFULL
Faroe Open-Back Printed Satin Maxi Dress
Just add brown knee-high boots.
Reformation
Evra Dress in Lydia
The burgundy tone brings this dress into winter.
Alexandra Miro
Ava One-Shoulder Maxi Dress
This dress is destined to turn heads.
Zebra is coming for leopard next year.
ULLA JOHNSON
Evangeline Striped Pleated Metallic-Knit Turtleneck Maxi Dress
I’ve had my eye on this dress since it first launched.
John Lewis
Rose Print Batwing Maxi Dress
ZARA
Flocked Tulle Maxi Dress
The back is so beautiful.