How to Wear Dresses in Winter... Without Catching a Cold

July 22, 2022

As temperatures fall below 20 degrees celsius (well below 20 in some areas — Victoria and Tasmania, we’re looking at you), most of us banish our dresses to the back of our wardrobes, where they’ll remain until spring comes around again. But it doesn’t have to be this way — dresses do have a place in your outfit rotation during these chillier months. If just the thought of slipping into your favourite midi dress has you shivering, we’ve got you covered. Below, we explain exactly how to wear a dress in winter without catching a cold. It can be done, we promise!

Styling a Dress for Winter

When it comes to wearing dresses in winter, the key is in how you style the dress. We’re firm believers that you can make any dress work for you in winter — yep, even mini dresses.

Let’s take a look at some tips for styling your dresses for the cooler days ahead.

Layering Summer Dresses for Winter

First, let’s consider how you can make some of your favourite summer dresses thrive in winter.

Hint: the secret is in layering and accessories.

Tip 1: Layer Up

Warmth is key — we’re not about catching colds for the sake of fashion. But that doesn’t mean your dresses are out of bounds. All you need to do is layer up!

Take your favourite mini-length LBD, for example. We love adding a long, oversized coat on top of a mini dress. Not only will you stay nice and cozy, but the contrasting lengths create a balanced look that really works for winter. If you’re feeling extra chilly, you could also add a longline cardigan as a middle layer.

As for keeping your legs warm, you may want to opt for a pair of tights. There’s something very chic (and very 90s) about a semi-sheer pair of tights under an LBD.

Tip 2: Say Hello to Knee-High Boots

You’ve seen them on all of your favourite celebs and street-style influencers. Knee-high boots are a must-have winter item.

Knee-high boots are key in transitioning your favourite summer dress to winter. They work particularly well with mini dresses, but can also be paired with midi or maxi dresses that have floaty hems or side-splits.

They’ll give your legs that extra bit of warmth and help to give your summer dress a wintery feel.

Tip 3: Consider a Statement Jacket

Looking to take your winter styling up a notch? Add a statement blazer or faux fur jacket on top of your favourite summer dress.

Let’s return to the LBD example. You’ve slipped on your mini-length LBD and added a pair of black knee-high boots to match. For a chic business-attire-meets-street-style look, add an oversized blazer the same length as your mini dress. It’ll keep you warm while transitioning your summer dress into the colder months with ease.

For the most daring among us, opt for a full-glam look by throwing on a faux fur coat. Faux fur coats are unmatched in coziness, and they exude old-world elegance — it’s a win-win!

Styling Maxi Dresses for Winter

While maxi dresses are more commonly associated with warmer weather (floaty, floral maxis are a suitcase essential for balmy beach holidays) there’s no need to bid them farewell just because of the chill in the air.

Maxi dresses can add contrast to your winter wardrobe; they help to break up the monotony of the structured silhouettes we commonly see during colder months.

Tip 1 – The Leather Jacket Layer

There are two options to consider when putting an outfit together: you can follow the same silhouette structure from head to toe — for example, pairing an oversized blazer with oversized wide-legged pants — or you can use contrasting silhouettes to balance out the look.

Adding a cropped leather jacket on top of your maxi dress is a good example of the latter approach. If you’ve opted for a floaty maxi dress, a cropped leather jacket adds an unexpected edge to the look. Leather jackets are a pillar of winter fashion, so popping one over your maxi dress instantly makes the look season-appropriate.

Leather jackets are also particularly useful if you’re petite. Layering a longline coat over a maxi dress could overwhelm your figure, but a cropped leather jacket does just the opposite. It cinches the waist and balances the proportions of the look, which creates the illusion of length in the body.

Tip 2 – Add a Faux Fur Vest

If you consider your style a little less edgy and a little more boho, we recommend layering a faux fur vest over your maxi dress. Faux fur vests work particularly well over long-sleeved maxi dresses — you’ll still want coverage on those arms!

When it comes to the dress itself, knitted or dark-based floral long-sleeved maxi dresses are ideal. Keep the look cohesive by opting for a faux fur vest that matches the outfit tonally. So, if you’ve opted for a red-based floral maxi, go for a mahogany brown faux fur vest. If your dress is light grey, go for a darker grey vest on top.

As for accessories, we love adding sunglasses to round out the boho-chic look.

Tip 3 – Consider Your Shoes

For a casual look, pair your maxi dress with chunky boots or sneakers. Maxi dresses can feel a little formal, so styling yours down with an unexpected white sneaker or combat boot gives the outfit a surprising edge.

If you are going for something a little more elevated, we love a sock boot. Sock boots fit closely to the foot, delivering a neat and streamlined shape. This creates the perfect contrast against a floaty, long maxi dress.

Styling Midi Dresses for Winter

Midi dresses are considered wardrobe heroes for a reason. They’re versatile, flattering, and can be easily transitioned from season to season with just a few adjustments to your accessories.

Whether you’re a knitted midi dress-lover or you’re all about a pleated hem, it’s time to retrieve your midi dress from winter-wardrobe exile.

Tip 1: Bring Out the Boots

While you can definitely pair sneakers with a midi dress, we generally recommend opting for boots instead.

A midi dress will generally cut off somewhere between the calf and ankle. When you pair your midi with sneakers, there will be a gap left between your shoes and the hemline of the dress. This creates a bit of a clunky ‘break’ in the outfit and interrupts the flow of the look.

When you go for knee-high or ankle-length boots instead, you avoid creating this gap between the hem of the dress and the shoe. This helps to lengthen your figure, as the eye is drawn in one continuous sweep down the body.

Want to really lean into this lengthening effect? Opt for pointed-toe boots!

Tip 2: Take On the Turtle Neck Trend

If you’re looking for a way to bring your slip dress or spaghetti strap midi to winter, popping a turtleneck on underneath is our favourite hack.

Opt for a thin, skin-tight turtleneck to avoid any bunching under your dress. Choose a turtleneck in a hue that complements the colour of your dress. Generally, white, black, or beige turtlenecks are safe.

If you’ve opted for a black slip dress, go for a white turtleneck underneath for a Parisienne flair. Alternatively, if you’re throwing on a bright orange midi, a black turtleneck makes for a great contrasting base.

Accessorise this look by throwing a coat or leather jacket over your shoulders and popping on a pair of sleek boots.

Tip 3: Layer For Your Silhouette

You can’t really go wrong when it comes to layering a coat or jacket over your midi dress. Our tip? Layer for your silhouette.

For those on the taller side, accentuate your height by adding a long coat over the top of your midi dress. The hem of the coat should be just above or equal to the hemline of the midi dress. This creates a chic, elongated silhouette. We recommend going for a classic trench coat or simple black wool coat.

If you’re petite and find your figure is swamped by lengthy coats, go for a cropped jacket instead. A short faux fur jacket or leather jacket will give you shape at the waist and lengthen your legs.

Styling Long-Sleeved Dresses for Winter

If you’re looking to stock up on some winter-appropriate dresses, long sleeves are a must.

There are three key long-sleeved styles to consider adding to your outfit rotation this winter. These styles return season after season and have long proven that they transcend trend cycles.

Consider these long-sleeved dresses investment pieces you’ll come back to each year.

Tip 1: Shirt Dresses

For an understated look, we love a good shirt dress. We’re talking an oversized, button-down shirt dress in classic blue or crisp white.

If you’re willing to brave the cold, go for a midi-length shirt dress with an oversized coat thrown over the top, and knee-high boots to complete the look.

Need a little extra warmth? Go for a slightly shorter shirt dress (thigh to knee-length is ideal) and keep the last few buttons undone. Add a pair of straight-cut jeans or leather pants underneath, and drape a coat or leather jacket over your shoulders.

Add sneakers to dress the look down, or elevate the outfit with heeled boots.

Tip 2: Knitted Dresses

Long-sleeved knitted dresses are an absolute must during winter. They’re chic, timeless, and oh so easy to style — you’ll be reaching for yours constantly this season.

For winter, we love knitted dresses in earthy hues. Think chocolate, olive, black, and grey tones.

Our favourite styling tip? Pair a long-sleeved black knitted dress with a black overcoat and boots, and add a scarf in a bright hue for a pop of colour. We’re loving cobalt blue or bright green.

Tip 3: Floaty Dresses

If you’re looking to take a break from your heavier winter-wardrobe items, go for a floaty long-sleeved midi dress.

Look to styles with pleated or tiered hems. Inject colour into your wardrobe by opting for a jewel-toned dress. Emerald green, royal blue, and ruby red all work well.

Alternatively, choose something in a dark-based floral print. These prints style well with dark or neutral-coloured coats, boots, and accessories.

When it comes to floaty silhouettes, it’s best to balance out the look by selecting a structured coat to layer on top. To prevent the outfit from appearing too busy, go for straight silhouettes rather than fit-and-flare designs.

What Do You Wear Under a Dress During Winter?

On the coldest of dress-wearing days, you might need a little extra warmth. So, what can you do to stay cosy and chic?

Tip 1: Add a Slip

Slips are seriously underrated.

They help to keep you warm and also stop your dress from clinging uncomfortably to your skin. We recommend going for a black, white, or beige slip, as these will work under most dresses.

Tip 2: Add Tights

Layer up by adding tights under your dress this winter. We particularly love tights paired with black or neutral-toned mini dresses and pointed-toe heels.