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Fashionable Dressing: How To Wear Dresses In Fall and Winter

Updated: Dec 13, 2023

How to stylishly wear your dresses in fall and winter.

tips on how women can wear dresses during fall and winter
How to Fashionably wear dresses in fall and winter

How to wear dresses in fall, or as we call it in the UK 'autumn', and look fashionable. Majority of dresses are designed to keep you cool, so when the weather changes and you are in need for more warmth it can be tempting to pack away those lovely pieces. Here at Calycious_Loves, we love versatile styling and making the most of our wardrobe - maximising cost per wear. Be rest assured that by the time you finish reading this blog post you will be confident enough to put those dresses on rotation during the colder months.

Here are some easy ways to make the most of your wardrobe by styling dresses in fall and winter.


Keep It Simple

Start small by wearing dresses that can easily be adapted to cold weather. Think below the knee and long sleeves, such dresses do not need a lengthy outfit formula, just add a warm blazer or jacket and you will be good to go.

Get Used to Layering

The secret, well not much of a secret but skill, is in putting the right pieces together to create a weather appropriate outfit. Take out the boringness in knit jumpers and put some sassy into them.

My favourite outfit formula for wearing a dress is: wearing a high waisted belt and a knit jumper on top. Then tuck the front of the knit jumper in the belt to create a feminine silhouette. Add warm boots and a coat for a stylish finish - WATCH VIDEO BELOW.

"the skill is in putting the right pieces together to create a weather appropriate outfit."

Turtlenecks Are Your Best Friend

Some dress are just showstoppers and it can feel like you are doing them injustice wearing knits or coats on top. Invest in a turtleneck, wear it underneath the dresS. Keep the cold at bay whilst keeping the dress star of the show.

a woman wearing a cami dress with a turtleneck underneath
styling a dress for fall winter

a turtleneck under a cami dress with knee high boots
How to wear a dress in fall winter

Footwear Is Key

I struggle when my feet are cold and the easiest way to stay fashionable and stylish in fall/winter is to have a good pair of boots.

knee high boots styled with a dress in fall winter
Make a wardrobe statement with fall winter boots

add warmth to dresses in fall and winter by wearing boots
Warm and stylish boots for fall winter

Think Hosiery

hosiery to keep warm in fall and winter
Warm hosiery is a fall winter must-have - opt for higher denier

To keep things warm, opt for thicker denier tights. If you struggle with your tights sliding down every time you style them, watch my YouTube video below for a great hack.

Fashionably wearing your dresses for fall and winter need not be stressful, start small and work with what you are most comfortable with and in no time you will be a pro.

Wearing a summer dress and styling it for fall winter by layering a blazer and trench coat
Outfit formula: Dress + Blazer + Trench Coat + Boots

In a nutshell, nothing is more satisfying that maximising your wardrobe. Click Here to watch a video I shared a few years on how I styled 1 summer multiple ways for winter for more styling tips. Please consider subscribing to my channel :). Thank you.


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