Longline coats and shorter jackets are typically safe bets because they either cover up the hem of the skirt or show it off, but with midi-length dresses, aim for a jacket that matches the hem to keep your look balanced and streamlined.

3. Boots and Shoes

At one time, wearing dresses with anything other than heels was unthinkable, but thankfully since then times have changed. Whether it's a pair of chunky combat boots worn with a prairie style dress or a pair of shearling sneakers worn with a chic pencil skirt, the options are endless, and much easier to get about in.

4. Don't Forget Your Thermals

Depending on how cold it is, it's up to you how warm you need your base-layer to be, but there are a few options out there, so decide which one is for you. Many stores now sell thermal tops and leggings made from material designed to adapt to your body temperature, while others such as Tencel^TM offer a kinder and more sustainable alternative to silk.

5. Layers

We've all heard how important it is to dress in layers during the colder seasons. The main trick is to make sure they're not too tight, to allow for air to circulate, and to help to insulate your body against the cold. For extra warmth, consider adding a piece of knitwear on top of your dress and under your jacket.

6. Sweater Weather

A sweater dress not only feels like being wrapped up in a blanket all day long; they can also look super chic. A classic fitted style with a roll neck will never steer you wrong, but if you're going for something a little looser, pay attention to accessories; for instance, a well-placed belt can add the perfect finishing touch.

7. How to Layer Your Knitwear

Mini dresses look fabulous with long-line cardigans and work surprisingly well with longer length sweaters. The ruffle of the hem at the bottoms can create a charming drop-waist look. If you prefer your hemlines a little longer, try tucking your sweater into a belt before blousing slightly to add a cropped effect, or knot it to one side for a more asymmetric look.

8. Add Some Winter Warmers

Gloves, scarves and hats are all great ways to accessorize your dress for winter, but pay attention to two key elements: suitability and coordination. To keep things simple, stick to a palette of your favorite colors and choose winter accessories that match your dress.

9. Fake the "Bare Leg" Look

Another thing we often see in fashion editorials and on Pinterest boards is bare legs paired with winter outfits. While this looks good in theory, in real life it can be another matter. If you love this look, nude fleece-lined tights are your new best friend. Be sure to double up with some long socks for added warmth. 

10. Legs for Days

One of the best things about fall and winter is the return of hosiery, especially if you prefer to wear shorter hemlines to show off your pins. These are no longer limited to black and nude options; now there's an array of designs and colors to choose from: you just have to decide what to match with your outfit.

11. Wear Your Summer Dresses

You can still wear your summer dresses even when the mercury dips. The main key here is to play with texture; since the majority of summer dresses tend to be floaty and light material (often with floral prints), try balancing out the look with a chunky sweater layered on top.

12. Winter, But Make It Glam

If you're headed on a night out, or to a more formal event, you don't have to shiver the night away: choose for cover-ups in luxe materials to contrast with your outfit: brocade jacquard or faux fur are all great options, but if you prefer something a little more minimal, for a classic, slightly oversized blazer looks chic while keeping you warm.

The Takeaway

Wearing dresses in colder weather can be a little challenging, leading to wardrobe mishaps that can mess with the overall look of your outfit, but with a little strategic layering and some careful coordination, you can create looks you'll want to wear all winter long.