When I say that winter is my favourite season to dress for, it comes with a caveat, and that’s when I have the time to do it justice. If the mornings are slower, I revel in layering up merino tops and cashmere finishes, mixing and matching knitwear and satins and indulging in playful accessories of cosy mittens and sleek scarves. But as the busiest time of the year, those languid mornings are few and far between, and getting dressed for the winter months 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 facing a day in the office, a stroll to your favourite coffee shop or even an evening out, simply let a maxi dress do all the heavy lifting this winter.
The elegance of the silhouette speaks for itself, meaning you don’t have to do much to form a seriously put-together look when there are only 5 minutes to get ready. For day, slip on boots or flats with a dash of classic jewellery and you’re all set, and for 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 all set to take on the day, come rain, shine or snow.
At this time of year, our dresses deviate from the linens of summer or light cottons of autumn and spring, honing in on soft knits for the day, and elegant silks for evenings. 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 the best winter maxi dresses now.
Shop the Best Winter Maxi Dresses:
1. The Best Knit Winter Maxi Dresses
Style Notes: For those who want to be cosy, a knit dress is ideal, and with an elegant silhouette, these can easily transform to evening as needed.
Shop the best knit 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 Mango’s classic knitted turtleneck dress.
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 pulled together a selection of compliment-inducing evening dresses in maxi form that you’re sure to re-wear come 2025.
Shop the best evening winter maxi dresses:
Reformation
Nemy Knit Dress
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
Scarf Dress X Kate Moss
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, as the Long Black Dress steps in. Find the best black maxi dresses for winter below.
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
It’s hard to believe this is from the high street.
Hush
Talen Long Sleeved Knitted Maxi Dress
For evening, I’d add oversized gold jewellery and a gold 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 are sure to be favourites through 2025 too.
Shop the best pattern winter maxi dresses:
FAITHFULL
Faroe Open-Back Printed Satin Maxi Dress
Just add brown knee high boots.
The burgundy tone brings this dress into winter.
Alexandra Miro
Ava One-Shoulder Maxi Dress
This dress is destined to turn heads.
RIXO
Suzanne – Zebra Black
I can see this selling out quickly.
ULLA JOHNSON
Evangeline Striped Pleated Metallic-Knit Turtleneck Maxi Dress
I’ve had my eye on this dress since it first launched.
John Lewis
John Lewis Rose Print Batwing Maxi Dress
ZARA
Flocked Tulle Maxi Dress
The back is so beautiful.