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Jeans, boots and jumpers.If that describes the extent of your winter style, you’re not alone.

When temperatures start to drop, our sartorial selves tend to go into hibernation, with even the most style-savvy among us choosing warmth over fashion and practicality over personality. But what if there was a way to keep cosy without abandoning that carefree one-and-done maxi dress feeling you enjoyed all summer? Well, there is, and it involves a few simple styling tricks that will help you keep snug and super chic, now and into the freezing cold months. This your guide for how to wear dresses in winter.

First, there are a few things you need to know about the winter dress. This is not just about throwing a jacket on top of your best-loved beach frock. Pack anything in lightweight cotton or an obviously summery print away in the cupboard, because right now, it’s about a deeper colour palette of autumnal hues and rich (but not necessarily heavy) fabrications – silks, denim, leather and even lace will easily cross over with some clever layering.

Consider accessories as your new best friend. While a sandal or sandshoe may have cut it in the warmer weather (and, let’s face it, may still be in rotation well past the appropriate time of year), it’s time to turn to well-maintained, closed-toe shoes and boots that can form the basis of your look. Waisted belts are big at the moment and can play a crucial part in pulling your ensemble together, not to mention giving your silhouette form, amid all those layers. And not to be overlooked, structured bags, statement sunglasses and even woolly hats can add an element of finesse to winter dress outfits.

Ultimately, what we’re aiming for is a winter look that appears polished yet takes minutes to master. Read on for nine winter dress ideas, from how to style a midi dress to cold-weather proofing your office dresses, nailing ankle boots with a dress, and season-appropriate dress colours and dress patterns. By the time you’re done, warm winter dresses will be your wardrobe mainstay. Bring on the big chill!

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1.Wear your dress
under a vest

If the words “sweater vest” are conjuring up long-forgotten memories of your fourth-grade maths teacher, it’s time to reframe your thinking. What was once seen as a dowdy throwback to the 1970s, is experiencing a return to fashion.

The latest knitted vests are modern and minimalistic, with a refined nomadic feel that perfectly complements the folk-style full-sleeved winter dresses that are so on-trend right now. And that might just be the best thing about the sweater vest – the ability to keep your core warm while still showing off what is typically the most striking feature of your dress, the sleeves.

Ways to Wear It:

In a fine cable knit, a wool vest is a great way to add an element of texture to an outfit, especially when your look is kept tonal. While creamy tones might feel more familiar, the knit vest takes on a dashing – dare we say darkly romantic – note when done in a midnight hue. Teamed with glossy leather accents like a long belt or alligator-effect boots, it’s an elegant way to encourage warmth without having to excessively rug up.

How to Style It:

The shape you’re looking for is slightly oversized, wide-on-the-shoulder and hip-length. It’s a style best worn with a midi-length dress to avoid the prep-school connotations that a mini hemline might suggest. And make sure your dress is in a fluid fabric that gives good contrast to the more structured vest.

Expert Tip:

Breaking the vest directly in half with your belt (tied in a casual knot around the waist) will help you minimise bulk around the middle while creating the illusion of length. A pair of knee-high, high-heeled boots add strength and balanced proportion to the look.

2.Layer your
dress over pants

Who ever said you can’t have your cake and eat it, too? If you want to try a winter dress but can’t quite let go of the pants, this look is for you. In perhaps the best alternative we’ve seen to trusty opaque hosiery, slim trousers or leggings layered under a dress is not only a fabulously functional workaround to ward off the biting cold on your work commute, but also a fashion-forward look that you can have some fun with.

The trick is to take the best elements of a look made popular in the 1980s (think Madonna circa Like a Virgin) and make it contemporary. While the strategy works with any skinny or straight-leg trousers, why not get adventurous with a leather legging? They will add just the right level of toughness to an otherwise classic outfit, and you can’t get a warmer pant without veering into tracksuit territory (which, comfy as they are, have no place under a dress).

Ways to Wear It:

There is one style of dress that is especially successful with this technique: the shirt dress. There’s a cool nonchalance to this perennial piece that means you can push up a sleeve, unbutton the hem and really make it your own. Choose a traditional longline white shirt for a timeless approach or get experimental with prominent details like outsized patch pockets, snap stud closures and statement sleeves.

How to Style It:

With attitude. Wearing a dress over pants requires confidence and intent. A sash belt decisively secured around the waist, a stiletto pump that showcases the ankles, even a flick of the hair to frame the collar is enough to elevate what is at its core an incredibly easy equation, aka dress plus pant.

Expert Tip:

Layering a basic tee under your shirt dress should get you by in a heated office but for cooler climates consider a fine thermal. While traditionally they’ve been a garment to be hidden away, some of the latest styles are more than fit for poking out of a neckline and will keep you toasty under denim or flannel without adding any extra thickness. We’d stop short of a long john unless you’re heading to the ski slopes – the best kind of layers are the ones you can easily slip on and off.

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3.Go grunge

Ok, so it’s not exactly Nirvana-era ‘90s grunge we’re referring to here. But there are elements emerging this season that give a nod to that iconic anti-fashion period while keeping this side of stylish and snug, which is the point.

Exhibit A: the check. Of all the winter patterns, this one would have to be the easiest and most striking to wear. Specifically, we’re talking plaid or tartan checks – stripes crossing each other in varying widths. With a long history of counterculture associations, including the Scottish Rebellion, punk movement and, of course grunge, plaid has shaken off its anarchistic reputation of late, yet retains a subversive subtext that can absolutely work in your favour. Done in a baby doll-style dress that employs a sweet cut, it’s a perfectly pitched juxtaposition for a winter dress outfit.

Ways to Wear It:

We say, go with it. No demure court shoes or ladylike handbags here. This type of winter dress needs to err on the side of cool rather than caution. So, channel the spirit of grunge and relax into it. A little slouch goes a long way.

How to Style It:

It’s the under-the-radar touches that count. A jacket or sweater tied around the waist will instantly achieve an alt rock attitude. A pair of dark glasses. A cross-body clutch bag. On-the-go pieces that appear effortless, and in this case, actually are.

Expert Tip:

Leave the stockings at home. A suede boot that reaches almost to the knee should be enough to keep your legs comfortable in the cold, but that flash of skin at the knee is essential to maintaining the edge on this outfit. If you’re still concerned, opt for a low denier stocking (between five and 30) that will still give the look while providing the sensation of covering up.

4.Add faux fur to
any dress outfit

There’s nothing quite like the feeling of cuddling up to faux fur, but while not every occasion calls for a Hollywood-worthy overcoat, a neat aviation jacket with soft furry trim is a city-ready alternative that will work – day in, day out. Like a scarf and leather jacket in one, the cropped coverall is just the thing to ready a flirty floral dress for the outdoor elements.

Ways to Wear It:

This is a youthful look that leans on casual but given the new normal work practices we’re adjusting to, it could just as easily stride into the office as stomping around on the weekend. The trick is to keep your colours earthy and tonal, and your floral print muted and micro – go too bold and you’ll upset the balance. That said, there’s no reason why you can’t play with unexpected colours like pistachio or rust when it comes to your faux fur – life’s too short to be limited to brown.

How to Style It:

The perfect grounding for this urban uniform also happens to be this season’s favourite footwear: the hiking boot. Slightly chunky, superbly practical and fit for winter pavement pounding, these utilitarian must-haves provide the perfect foundation for a flighty dress and fanciful faux fur. Wear them with long, fine rib socks, pushed down for a look that says you’re straight from the hiking trail.

Expert Tip:

Save the deep V neckline for warmer weather and layer a fresh white crew-neck tee underneath your dress and keep your chest stylishly protected from the elements.

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5.Try the
sweater dress

Remember when we said it was possible to embrace that one-and-done feeling you so loved last summer? Well, winter’s answer to the t-shirt dress is here: the high-neck, long-sleeved, ribbed sweater dress. It’s a non-negotiable must-have in any woman’s wardrobe, not only for the chic factor but because it will hands-down be the single most comfortable dress you own.

Ways to Wear It:

While any length is a good length when it comes to a sweater dress, the latest styles typically fall to mid-thigh, with a studied slouch and scrunch about the sleeves, room through the body and slim across the hips. Anything goes when it comes to neckline, though a funnel (where the fabric stands against the neck) or turtleneck (where the fabric folds over) is the most sensible and, fortunately for us, the most sophisticated.

How to Style It:

If you’re after that rich-girl glamour then toffee tones should be your go-to. Not only because they look expensive (even if they’re not) but because they lend themselves to luxurious leather accessories in interesting autumn colours like cherry or oxblood. If you’re keeping your hemline short, then opt for larger accessories to offset the proportion. This is your chance to whip out your knee-high or over-the-knee boots – worn with a sweater dress, it’s a perfect match.

Expert Tip:

Wearing a short slip underneath means the ribbed fabric will skim, not cling, to your curves, while also solving any static issues that may arise, especially if you choose to team with tights.

6.Get sporty

It goes without saying, wearing a dress doesn’t have to mean dressing up. In fact, it can mean exactly the opposite. Dressing down no longer involves Lycra exercise tights – we’ve all seen more than our fair share of those lately. Now, we want our leisure wear to feel, well, leisurely. And the right dress can deliver on the need for a laid-back look that still has one sneakered foot firmly in fashion.

Ways to Wear It:

The look involves a dress that’s form-fitting; a streamlined silhouette with an element of stretch, perhaps the perfect traditional winter office dress. A long-sleeved, high neck knit dress in a neutral colour will provide the best base to build on and can be worn time and time again with an easy tweak of a jacket, shoe or accessory.

How to Style It:

A jacket with some volume to it will balance your body-skimming tube dress. A quilted parka, cropped at the hip for a longer dress or reaching the hemline of a shorter one, is an ideal choice that’s incredibly flattering and fit for whatever the weather throws your way. Teamed with a chunky leather sneaker, the combination has a sporty vibe without looking like you’ve just rolled in from the gym.

Expert Tip:

A word on winter headwear. There is no single piece that will keep you more cosy in a cold snap than a hat. Yes, your mother was right. If your head is uncovered, you’ll lose body heat – up to 50 per cent of it according to Harvard Medical School – even if the rest of your body is rugged up. Good news is – beanies are back. Find one that fits snug to the head and covers your ears and make your mum proud.

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7.Double up
on leather

There are not many items that come under the banner of fashion that carry the same kind of longevity as leather. It’s luxe, for sure, and incredibly of-the-moment, but it’s also exceptionally durable and – in the right shape – can be timeless. At a time when we all need to be considering where our purchases end up, it’s encouraging to know that a well-chosen leather piece will age beautifully with you.

The key is in the choosing. Your investment piece doesn’t have to be trendy, edgy or rewrite the style rule book. What it does need to be is chic and classic, with the ability to make you feel amazing. No pressure – you’ll know when you see it, though. A buttery smooth feel, a tailored cut, quality finishes and a deep, rich colour that will instantly chime with everything else you own. If you love it now, chances are you’ll love it forever.

Ways to Wear It:

Look for pieces that have already proven their staying power. The leather coat dress, for one, is a recurring style that has reigned supreme since the 1970s. If you’ve ever scoured a vintage store for this gem, you’ll know they don’t stay on the rack for long. Stiff leathers don’t lend themselves to this button-up style so it’s all about a super soft material that already feels lived in and can be worn over light layers.

How to Style It:

If we’re talking long-term investments then the next item on the list is a knee-high boot. Look for a rounded point, room through the leg and a colour that will look just as good pulled over denim as it does peeking out under the hem of your leather dress.

Expert Tip:

Choosing a button-down leather dress with a coordinating belt means your item can work overtime, left open over trousers and worn as a coat.

8.Play with
knitwear

How to wear a spaghetti strap dress in the winter? Knitwear. The best way to shore up a sheer dress? Knitwear. And how about a flippy dress that feels a tad too frivolous for the office? You guessed it, knitwear. An instant fix for almost any dress deficiency: a great knit that can be layered over the top. Not to cover up, but to complement and enhance.

Ways to Wear It:

That’s not to say you can just pull on the shaggy knit you wear down to the shop on your weekend milk run. But a well-cared-for sweater can upgrade your favourite floaty dress and feel reassuringly appropriate for almost any occasion. Tone the knit in with your frock, keeping to a palette of navy, grey and black for ultimate understated elegance.

How to Style It:

A long cardigan, loose-fitting turtleneck, or cape-style knit can transform a dress, whether a mini that falls above the knee or a maxi length that scrapes the ankle. Leave your knit loose for a less styled approach or step it up with the simple addition of a knotted belt.

Expert Tip:

Suede boots in a complementary colour create a cool texture play against a fuzzy knit and fluid dress. Opt for either an ankle or knee-reaching height.

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9.Embrace the
winter skivvy
underneath a
dress

Our final winter dress style tip is arguably the easiest, quickest, chicest hack you’ll try all winter, and it involves an underpinning you’ve probably worked hard over the years to eradicate from your wardrobe. But trust us when we say that a skivvy or three (black, grey and cream) will undoubtedly be the best purchase you make all season.

Ways to Wear It:

The look is most successful when wearing a dress with sleeves. This way the skivvy shows at the forearms and neck but leaves the focus on your dress, which is still the star of the show. This is not a job for a bulky turtleneck – a very fine gauge wool knit with a slim-fitting neck and sleeve is what you’re after.

How to Style It:

For a nice finishing touch, add some delicate pieces of silver jewellery on your fingers or ears, leaving the neck and wrists free.

Expert Tip:

Choose a knit that is long in the body as there is truly nothing worse than an under layer riding up around your middle.

A Note On Styling Your Winter Dress

We get it. Winter dressing can be overwhelming. Which is the best knit? How many layers is too many? Why won’t these stockings stay up? It can be especially challenging for those living in warmer climates who can get by nine months of the year with barely a jacket. That’s why mastering the winter dress can be your style saviour.

The three takeaways? Choose pieces you feel good in. Stick to a neutral colour palette. Get yourself a killer pair of boots that you can walk a mile in. Oh, and continue to wear sunscreen. It can be as simple as that.