How to Style Dresses for Winter

by ANTOINETTE STONHAM

6 Easy Tips to Stay Warm and Stylish

Do you have favourite dresses you wore over and over again through the summer months?
Good news, you don’t need to pack them away just because the weather’s cooled down! With the right layering tricks and cosy accessories, you can enjoy your dresses all year round. 

Whether you're grabbing coffee with a friend, heading to the office, enjoying date night, or just creating something fresh for your everyday wardrobe, these six tips will help you style your dresses for winter without sacrificing warmth or style.

1. Start with Smart Layering

One of the easiest ways to convert your summer dresses for use in the cooler months is by layering underneath. Thermal singlets play an important part in the art of layering. You can also wear long-sleeved tops, fitted turtlenecks, or shirts underneath. This is especially great with sleeveless or slip-style dresses and give your outfit a warm and stylish 'look'.
Stick to neutral or tonal colours for a streamlined look, or have fun with contrasting shades for a pop of personality.

2. Add Tights or Leggings

Tights are your winter best friend, warm without the bulk. Choose opaque, thermal, or fleece-lined options to suit your climate. Do you really feel the cold? Try thick leggings paired with tall boots for extra insulation.

I personally love patterned or coloured tights as they add both fun and texture to any outfit.

3. Knitwear is Your Secret Weapon

If you throw a jumper over your dress you’ll have created a top-and-skirt look!
Go for lighter knits or cropped styles so you don’t overwhelm your shape. Jumpers that are too long will unbalance your body shape.

If you're an hourglass or triangle shape, a cropped knit is especially flattering. My favourite trick? Add a belt to highlight your waist and pull the look together.

4. Invest in a GREAT Coat

I may not love cold weather, but I do love a fabulous winter coat!
A long, elegant coat instantly makes your winter outfit look fabulous and keeps you warm. It’s perfect for throwing on top with a scarf when you’re running out the door. No one will ever know you are secretly in a track suit underneath.

A good quality coat that will last for years is a big investment.
Before buying one, consider your lifestyle, personality, colour palette and the style of coat that will suit you best. Whether it is a wool coast, puffer or trench, choose something that hits below the knee or full length for maximum warmth and style. 

Choose a style that’s roomy enough for layering underneath, especially around the shoulders and arms. A wide or coloured belt will give your outfit structure, and a point of difference if you want to change the style. 

5. Accessorize with Purpose

Accessories are going to be your best friend.  Oversized scarves, beanies, berets not only keep you warm, but add texture, colour and personality to your outfit. 

So don't be afraid to express your personality with a bold or patterned scarf or a fun fuzzy hat. You can transform a basic outfit and bring a plain dress to life. 

6. Choose the Right Footwear

Boots are a winter must-have. Whether knee-highs, mid-calf, ankle boots or a fun furry style, they keep you warm while adding a touch of style to your outfit. This year I’m loving block heels, chunky soles, and textured finishes.

Want a bit of fun? Try chunky boots with knee-high wool socks peeking out—it’s a great look and adds extra warmth.

Bonus Tip: Layer Smarter, Not Heavier

To avoid that bulky feeling, start with thinner layers (like thermals or fitted knits) and work your way outwards to heavier ones (coats and scarves).
Smart layering lets you peel off as the day warms up—and stay comfy from morning to evening.

Remember, ladies: shop your wardrobe first.

Start by styling the dresses you already love. Take some photos of outfit combos, note down what’s missing, and then hit the shops with purpose.

If you loved this post, be sure to subscribe to the blog (or our YouTube channel!) for more styling inspiration.  And remember to share this with a friend who’s always cold but still wants to look stylish!