June 3, 2023

The appeal of dresses is how easy they are to wear and the fact that they require little to no styling. This is certainly true in summer. However, in winter, it gets a little trickier, as you have the cold to contend with and layers become vital. I personally find myself wearing jeans and trousers with a jumper far more appealing than my usual uniform, a dress. But there are some styling tricks that you can do to make your dresses more winter appropriate, and below, I’ve listed eight in particular that I’ve saved recently.

If you opt for a simple slip dress or black dress, you can use it as a clever layering piece and wear it over roll-necks or long-sleeved tops. A dress, blazer and boots will be a trio that won’t need any introduction to you, but it’s a classic winter outfit that will always look elegant. The key to making a dress work hard in winter is the right pair of boots, and below, there are several styles that look amazing, including chunky hiker boots, cream knee-high boots and white ankle boots. If you are in need of some styling inspiration, keep scrolling for eight cool ways to wear a dress this winter.

1. Red Blazer + Cream Knit Dress

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Mango Woollen Wrap Suit Jacket
Mango
Woollen Wrap Suit Jacket
£80

Mango Ribbed Knit Dress
Mango
Ribbed Knit Dress
£36

The Row Everyday Small Brown Leather Shoulder Bag
The Row
Everyday Small Brown Leather Shoulder Bag
£1950

2. Black Slip Dress + Cream Roll-Neck

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12 Storeez Open Back Slip Dress
12 Storeez
Open Back Slip Dress
£140

& Other Stories Fitted Rib Top
& Other Stories
Fitted Rib Top
£27

Aquazzura So Nude 105 Gold Leather Sandals
Aquazzura
So Nude 105 Gold Leather Sandals
£440

3. Feather-Trimmed Dress + Spotty Tights

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Kitri Carlotta Malachite Print Mini Dress
Kitri
Carlotta Malachite Print Mini Dress
£145

Aeyde Donna 55 Silver Leather Ankle Boots
Aeyde
Donna 55 Silver Leather Ankle Boots
£325

Heist The Polka Dot
Heist
The Polka Dot
£28

4. Blazer + Slip Dress

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Arket Oversized Wool Hopsack Blazer
Arket
Oversized Wool Hopsack Blazer
£135

Vince Navy Hammered Satin Slip Dress
Vince
Navy Hammered Satin Slip Dress
£280

Paris Texas Kiki 100 Ivory Leather Knee-High Boots
Paris Texas
Kiki 100 Ivory Leather Knee-High Boots
£615

5. Knitted Vest + Oversized Black Dress

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Ganni Logo-Jacquard Wool-Blend Vest
Ganni
Logo-Jacquard Wool-Blend Vest
£160

COS Puff Sleeve Dress
COS
Puff Sleeve Dress
£79

M&S Collection The Chunky Leather Chelsea Boots
M&S Collection
The Chunky Leather Chelsea Boots
£69

6. Floral Dress + White Boots

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Doen Eugenie Lace-Trimmed Floral-Print Crepe Dress
Doen
Eugenie Lace-Trimmed Floral-Print Crepe Dress
£249

BY FAR Sofia 65 Off-White Leather Ankle Boots
BY FAR
Sofia 65 Off-White Leather Ankle Boots
£405

7. Navy Coat + Floral Dress

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COS Belted Wrap Coat
COS
Belted Wrap Coat
£190

& Other Stories Statement Collar Floral Mini Dress
& Other Stories
Statement Collar Floral Mini Dress
£75

Arket Chunky Leather Boots
Arket
Chunky Leather Boots
£175

8. Black Mini + Striped Jumper

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& Other Stories Half-Zip Sweater
& Other Stories
Half-Zip Sweater
£95

Ba&Sh Dress Faya
Ba&Sh
Dress Faya
£143

Alexander McQueen Wander Black Glossed Leather Chelsea Boots
Alexander McQueen
Wander Black Glossed Leather Chelsea Boots
£690

Next up, see our guide to the key trends for autumn/winter 2021.